Tag: M.W=200-300

Reference of 1092460-79-1, A common heterocyclic compound, 1092460-79-1, name is 3-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 3-chloro-4-(trifluoromethyl)-benzonitrile (2 g; 98%; 9.53 mmol) in CHCI3 (16 ml) and MeOH (4 ml) was cooled to 0C. Then HCl-gas was bubbled through this solution for 45min. The flask was closed and stored overnight in the fridge. Then argon was bubbled through to remove excess of HCl-gas and all solvents were evaporated. NH3 (2M solution in MeOH; 24 ml; 47.7 mmol) was added and the solution was stirred at RT for 2 h. The reaction mixture was concentrated to dryness. Then again NH3 (2M solution MeOH; 24 ml; 47.7 mmol) was added and the reaction mixture was stirred at RT overnight. The solvents were removed and the remaining white foamy solid (2.56 g) was used without purification for the next step. MS (ESI): 223.1 (M+H)+.

The synthetic route of 1092460-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAAP, Wolfgang; KUEHNE, Holger; MAUSER, Harald; (95 pag.)WO2016/87352; (2016); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 90110-98-8 as follows. Recommanded Product: 90110-98-8

1.4 (Z)-3-bromo-N’-hydroxy-4-hydroxymethyl benzamidine (1-3) Hydroxylamine hydrochloride (0.524 g, 7.54 mmol) and sodium bicarbonate (1.27 g, 15.08 mmol) were added successively to a solution of 3-bromo-4-hydroxymethyl benzonitrile (1-2, 0.80 g, 3.77 mmol) in methanol (120 mL) to obtain a suspension which was then heated to reflux for 5 hours. It was then cooled down to room temperature and filtered. The filter cake was washed with methanol (10 mL), and the filtrate was concentrated to obtain 3-bromo-N’-hydroxy-4-hydroxymethyl benzamidine which was a white crude product (1-3, 0.90 g, 97% yield), which was directly used in the next step. The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 245/247 [M+H]+.

According to the analysis of related databases, 90110-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUZHOU CONNECT BIOPHARMACEUTICALS, LTD.; ZHENG, Wei; PAN, Wubin; YANG, Xin; (47 pag.)EP3048103; (2016); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3108-23-4, name is 4,4,4-Trifluoro-2-(4-fluorophenyl)-3-oxobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3108-23-4

Reagents and conditions: (a) EtONa, EtOH, refluxing; (b) CH3NHNH2, HC1, EtOH,MW, 100C, 40 mm; (c) Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoyl chloride,DCM, then DBU. A mixture of 1.8 ml (15 mmol) of ethyl 2,2,2-trifluoroacetate (ib)and 0.96 g (7.1 mmol) of 2-(4-chloro-2-fluorophenyl)acetonitrile (3a) in 10 ml ofethanol was slowly dropped into hot solution of 1.2 g of sodium in 20 ml of ethanol.The mixture was refluxed overnight. The solution turns red. After cooled down, thesolution was poured into 250 ml of cold water acidified with 10 ml concentrated HC1.The mixture was extracted with ethyl acetate. The ethyl acetate extraction was washedwith water, brine and dried over Mg504. Ethyl acetate was removed and the residualreddish oil of 4,4,4-trifluoro-2-(4-fluorophenyl)-3 -oxobutanenitrile (3c) was obtained in1.3 g. The raw material was dissolved in 10 ml of ethanol and used in next step withoutfurther purification. A mixture of 2.8 ml of the above ethanol solution and 125pi ofmethylhydrazine with 0.2 ml of concentrated HC1 was irradiated in microwave oven at100C for 40 mm. The solution was treated with saturated NaHCO3 and extracted byethyl acetate. The organic layer was washed with water, brine, dried over Mg504 andconcentrated. The yellow residue was subjected to flash chromatography purificationwith MeOHIDCM to give 165 mg of 3-(trifluoromethyl)-4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-amine (3d) as light yellow solid. ?H NMR (500 MHz, CDC13) 7.32 (s,2H), 7.14 (t, J = 8.0 Hz, 2H), 3.76 (d, J = 33.5 Hz, 3H), 3.65 (s, 2H). M/Z =260.6(M+1). To a solution of Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoyl chloride (43mg, 0.20 mmol) produced from Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoic acid(from Chem Impex International) and thionyl chloride in 10 ml of anhydrous DCM were slowly added 3 -(trifluoromethyl)-4-(4-fluorophenyl)- 1-methyl-i H-pyrazol-5 – amine obtained as described above (39 mg, 0.15 mmol) in 5 ml of anhydrous DCM. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with methanol and solvents were removed. The residue was purified via silicagel with MeOHIDCM to obtained Fmoc protected product. Fmoc protected product was dissolved in 10 ml of ethyl acetate and 0.15 mmol of DBU was added. After 20mm 20 ml of ethyl acetate was added and mixture was washed with 20 ml of water. The organic layer was collected and solvent was removed. The residue was dissolved in MeOH and acidified with 0.2N HC1. The solution was purified via preparatory RP-HPLC, elutingwith H20/CH3CN gradient (+0.05% TFA). Product fractions are collected and concentrated. The residue is dissolved in a small amount of 2M HC1 in methanol and, after concentration in vacuo, 50 mg of Compound (3) is obtained as an HC1 salt. ?H NIVIR (500 IVIFIz, MeOD) 7.40 – 7.08 (m, 6H), 7.02 (t, J = 8.8 Hz, 2H), 3.77 (d, J = 15.4 Hz, 3H), 3.37 (dt, J = 7.9, 6.6 Hz, 1H), 2.64 (m, 2H), 2.42 (m, 2H). M/Z 439.4(M+i).

The synthetic route of 3108-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; DREXEL UNIVERSITY; UNIVERSITY OF WASHINGTON; BURROWS, Jeremy; WYVRATT, Matthew; VAIDYA, Akhil; KORTAGERE, Sandhya; FAN, Erkang; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; KATO, Tomoyo; WO2015/8246; (2015); A1;,
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Electric Literature of 57381-41-6, A common heterocyclic compound, 57381-41-6, name is 2,5-Dibromobenzonitrile, molecular formula is C7H3Br2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The 5.00g (19.16mmol) 2,5- dibromobenzene cyanide, 24g (76.65mmol) 1- (4- methoxybenzyl) pyrazole boronic ester, 11.64g (76.65mmol) of cesium fluoride, 1.11g ( 0.96 mmol) tetrakis (triphenylphosphine) palladium, ethylene glycol dimethyl ether was added to 300mL 500mL three bottles, sealed, vacuum, nitrogen atmosphere, for 6 hours at 100 .After stopping the reaction, extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure, purified by silica gel column chromatography purification, 2,5-bis (1- (4-methoxybenzyl ) lH-pyrazol-4-yl) benzyl cyanide 6.5g, yield 71.33%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Beijing industry university; Li, Jianrong; He, Tao; Xie, Yabo; Bai, Jinquan; (10 pag.)CN105541717; (2016); A;,
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Electric Literature of 134604-07-2, A common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Description for D422-(2-methylpropyl)-5-nitrobenzonitrile (D42)To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D42) (11 g) as a light yellow oil. deltaEta (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1H, dd), 8.51 (1H, d).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; ZHANG, Haibo; WO2011/113309; (2011); A1;,
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Synthetic Route of 57381-37-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under the protection of nitrogen,To 2-(3-((6-fluoroquinolin-4-yl)oxy)-8-azabicyclo[3.2.1]oct-8-yl)propanamide (100 mg, 0.3 mmol),2-bromo-5-chlorobenzonitrile (63 mg, 0.3 mmol) and NaOH (14 mg, 0.3 mmol) in 2 mL of NMPCuI (6 mg, 0.03 mmol) was added to the solution.The reaction mixture was stirred at 120 C overnight.The reaction system was poured into 10 mL of water.Extract with EA (10 mL x 3).The organic phase is washed with saturated brine.Dry anhydrous Na2SO4 and concentrate under reduced pressure.The residue was chromatographed on silica gel (DCM:MeOH = 10:1)Purification afforded 30 mg (yield: 21%) of the title compound.It is a white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chengdu Hai Borui Pharmaceutical Co., Ltd.; Chengdu Beite Pharmaceutical Co., Ltd.; Huang Haoxi; Liu Guanfeng; Ren Junfeng; Yi Shoubing; Chen Tonghun; He Quanhong; Wu Xiancai; Li Yingfu; Su Zhonghai; (91 pag.)CN109575022; (2019); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8F4N2

With reference to Compounds 15 and 16, an exemplary synthesis and characterization of F34 cZn (hereinafter “Compound 15″) and F52Pc’Zn (hereinafter”Compound 16”) are depicted. In particular, twenty (20) thick walled glass reaction vessels(about 10 mL volume) are charged each with about 0.4 g (about 0.62 mmol) perfluoro-3,5,6- triisopropyl phthalonitrile, (depicted in FIG. 1 1 as P3 and hereinafter “Compound 14″), about0.04 g (about 0.2 mmol) tetrafluorophthalonitrile (depicted in FIG. 1 1 as P0 and hereinafter”Compound 13”) and about 0.04 g (about 0.22 mmol) zinc(II) acetate dihydrate. Then, catalytic amounts of ammonium molibdate, and about 1 mL nitrobenzene are added to each vial. The sealed vessels are heated in a microwave reactor at approximately 180 ¡ãC for about1 min. The crude solid of each vial is extracted with about 50 mL ethyl acetate, the organic fractions are combined, concentrated in vacuo and adsorbed to silica gel (mesh size approximately 70-230). Gel filtration using an acetone/hexane approximately 2:98 mixture(v/v) allows for the complete separation of nitrobenzene, unreacted Compound 14 and most yellowish impurities. The resulting blue-green solid is collected and subjected to column chromatography under gradually increasing solvent polarity. The rest of yellow impurities are removed with acetone/hexane approximately 2:98 mixture, followed by the separation of the green exemplary F52Pc’Zn, eluted with an approximately 10:90 mixture, the royal blue exemplary F34PcZn at approximately 20:80 polarity, and finally the dark blue exemplary Fi6PcZn as a side product using an approximately 40:60 mixture (v/v). The three colored fractions are evaporated and re-purified by gel filtration on short columns, eluting with the corresponding mixtures used for their initial separation. Removal of the solvent and drying of the compounds allows for isolation of exemplary FsaPc’Zn in about 13percent yield (about 0.42 g), exemplary T^PcZn in about 16percent yield (about 0.26 g) and exemplary FigPcZn in about 14percent yield (about 0.1 g), all based on starting material Compound 13.[0098] Specifically, the exemplary properties for Compound 15, i.e., F34PcZn, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): max (log e) 689 (5.09), 672 (4.99), 632 (4.44), 614 (4.41), 365 (4.69) nm (L mol 1 cm 1); IR (KBr): 1522, 1489, 1383, 1282, 1236, 1 133, 964 cm”1; 19F NMR (282 MHz, (CD3)2CO): delta -69.05 (6F, br, CF3), -72.25 (12F, s, CF3), -97.12 (IF, s, Ar-F), -131.4 (IF, s, CF), -135.09 (I F, d, Ar-F), -139.18 to -141.66.(5F, m, Ar-F), -149.92 to -151.6 (6F, m, Ar-F), -161.39 (IF, d, CF), -165.99 to -170.18 (I F, m, CF); HRMS (APCI+): calcd. for [M + H]+ (C4iHF34N8Zn)+ 1314.9067, found 1314.9080.[0099] With reference to FIG. 12, the measured exact mass spectrum (positive ion APCI) and isotope pattern of [M + H]+ for F34PcZn are depicted, indicating the calculated value for [M + H]+.[00100] Turning now to FIGS. 13(a)-(b), the UV-Vis electronic absorption spectra of F34PcZn are illustrated, showing solvent- dependent aggregation. In particular, FIG. 33(a) illustrates a spectrum recorded in chloroform, in which F34PcZn is a monomer, and FIG. 13(b) illustrates a spectrum recorded in ethanol, in which F34PcZn displays a significant degree of dimerization.[00101] Further, the exemplary properties for Compound 16, i.e., F52Pc’Zn, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): Xmm (log epsilon) 701 (5.10), 674 (4.97), 640 (4.62), 615 (4.44), 372 (4.78) nm (L mol”1 cm”1); IR (KBr): 1523, 1489, 1375, 1287, 1236, 1 166, 1 127, 1050, 966, 939, 737 cnT1 ; 19F NMR (282 MHz, (CD3)2CO): delta -63.23 (3F, br, C3/4 -68.52 (3F, br, CF3), -70.69 to -76.31 (30F, m, CF ), -97.56 (2F, br, Ar-F), -130.85 (I F, d, CF), -137.91 to -141 .55 (5F, m, Ar-F), -151.23 to -152.76 (4F, m, Ar-F), -161 .49 (I F, d, CF), -166.47 to -170.15 (3F, m, CF); HRMS (APCI+): calcd. for [M + H]+ 1764.8780, found 1764.8804.[00102] With reference to FIG. 14, the measured exact mass spectrum (positive ion APCI) and isotope pattern of [M + H].bul. for F52 c’Zn are depicted, indicating the calculated value for [00103] Turning now to FIG. 15, the X-ray structure of F52Pc’Zn(OPPh3) is depicted, showing a metal-coordinated triphenyl phosphine oxide molecule. The thermal ellipsoids are plotted at about 35percent probability and rotational disorder of the CF3 groups of -C3F7 is present, specifically shown as dashed lines.[00104] With reference to FIG. 16, the side view of the aggregation in solid state of F52Pc’Zn is illustrated. In particular, the toluene molecules in the crystalline lattice and the atoms of coordinated triphenyl phosphine oxide, except oxygen, have been omitted. Further, the /-C3F7 groups are shown in ball-and-stick representation and the interplanar stacking distance, approximately 3.663 A, proves the existence of pi-pi interactions.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1835-65-0.

Reference:
Patent; NEW JERSEY INSTITUTE OF TECHNOLOGY; GORUN, Sergiu, M.; LOAS, Andrei, Ioan; GRISWOLD, Kimberly; LAPOK, Lukasz; PATEL, Hemantbhai, Hasmukhbhai; GERDES, Robert; WO2012/61344; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1953-99-7, Application In Synthesis of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

To a 100 ml flask were added 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dibromophenol (2.45 g), K2CO3 (3.9 g) and N,N-dimethylformamide And the mixture was stirred while heating to 70 ¡ã C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and vacuum dried to obtain 3,4,6-trichloro-5-(2,6-dibromo-phenoxy)-phthalonitrile.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samsung SDI Co., Ltd; Seo Hye-won; Shin Myeong-yeop; Jeong Ui-su; Han Gyu-seok; (56 pag.)KR2019/11995; (2019); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Step 1 4-chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile 185b 2-Bromo-4-chloro-benzonitrile 185a (5.92 g, 27.33 mmol, prepared by a known method disclosed in “”) was dissolved in 180 mL 1,4-dioxane, then compound 1d (5 g, 27.33 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.03 g, 2.73 mmol) and potassium carbonate (11.33 g, 81.98 mmol) were added. Under an argon atmosphere, the reaction solution was warmed up to 110C, and stirred for 16 hours. The reaction solution was naturally cooled to room temperature, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column with elution system B to obtain the title compound 185b (6.5 g, yield: 86.59%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 57381-49-4.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); A1;,
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Electric Literature of 90357-53-2, A common heterocyclic compound, 90357-53-2, name is N-(4-Cyano-3-(trifluoromethyl)phenyl)methacrylamide, molecular formula is C12H9F3N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 29; S-r¡ã-Fluoro-phenvO-S-methYl-S^-dihydro-SigmaH-pyrazole-S-carboxylic acidM-cvano-S-trifluoromethyl-PhenvD-amide and S-r¡ã-Fluoro-phenvO-S-methvM.S-dihvdro-SH-pyrazole-S-carboxylic acid r¡ã-cvano-S-trifluoromethyl-phenvQ-amide; Compound No.1 and Compound No.64; 2-[(1 E)-(4fluorophenyl)methylidene] toluenesulfonylhydrazone, prepared according to the procedure described in Example 29 (600 mg, 2.1 mmol) in THF (20 ml) was treated by NaH (60%, 120 mg, 3 mmol) at 0C for 20 min, followed by the addition of N-(4-cyano-3-trifluoromethyl-phenyl)-2-methyl- acrylamide (500 mg, 2.0 mmol). The reaction mixture was then heated to 55C overnight, then quenched by NaHCO3, and extracted by ethyl acetate. The organic layer was combined, washed with brine, dried over Na2SO4 and concentrated to yield crude product as a mixture. Purification of the crude product on a column yielded the title compound as separate products, as a white solids.5-(4-Fluorophihenyl)-3-methyl-3,4-dhydro-2H-pyrazole-3-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide (Hexane: ethyl acetate, 2:1 , Rf= 0.45, 475 mg, 61 %)5-(4-Fluoro-phenyl)-3-methyl-4,5-dihydro-3H-pyrazole-3-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide(Hexane: ethyl acetate: 2:1 , Rf=0.6, 100 mg, 13%): MS (m/z): MH+ (391) EPO 1H NMR (CDCI3) delta 8.50 (s, 1 H), 8.10 (s, 1 H), 7.90 (del, J=1.5 Hz, 0.2 Hz, 1 H), 7.75 (d, J=1.5 Hz, 1 H), 7.20 (m, 2H), 7.10 (m, 2H), 5.60 (t, J=0.9 Hz, 1 H), 3.00 (dd, J=1.0 Hz, 0.8 Hz, 1 H), 1.87 (s, 3H), 1.55 (t, J=1.1 Hz, 0.6 Hz, 1 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/55184; (2006); A2;,
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