Month: March 2021

606080-43-7, name is Methyl 2-cyano-5-fluorobenzoate, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

b) Synthesis of 2-Cyano-5-dimethylamino-benzoic acid methyl ester (21b). To a stirred solution of 4.03 g (22,5 mmol) 21a and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 15h at 65C in an autoclave and is reduced with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 21b is obtained in 89.0 % yield (4.09 g, 20.0 mmol). MS-ESI: 205 (M+ +1, 100),

The synthetic route of 606080-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); A1;,
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Synthetic Route of 915394-28-4, 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. 915394-28-4, name is 2-Methyl-2-(3-nitrophenyl)propanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95%). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 7.06 (t, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 6.52 (d, 1H), 5.21 (s, 2H), 1.61 (s, 6H). MS (ESI+, m/z): 161 [M+H]+

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-Methyl-2-(3-nitrophenyl)propanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANMI PHARM. CO., LTD.; Bae, In Hwan; Han, Sang Mi; Kwak, Eun Joo; Ahn, Young Gil; Suh, Kwee Hyun; US2015/191450; (2015); A1;,
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Synthetic Route of 501420-63-9, 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 501420-63-9 as follows.

To a stirred suspension of NaH (16.3 g, 406 mmol, 3 eq) in anhyd THF (100 mL) at 0 0C was added dropwise a solution of 2-(3-bromo-4-fluorophenyl)acetonitrile (29 g, 135 mmol) in anhyd THF (200 mL). After stirring Ih, MeI (42.1 mL, 675 mmol, 5 eq) was added to the reaction mixture. After stirring 2h at 0 0C, the reaction was allowed to warm to room temperature, quenched carefully with H2O and extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4 and evaporated in vacuo to give 2-(3-bromo-4- fluorophenyl)-2-methylpropanenitrile (29 g, 88%). 1H NMR (400 MHz, CDCl3) delta 7.66-7.64 (m, IH), 7.44-7.40 (m, IH), 7.15 (t, J=8.4 Hz, IH), 1.72 (s, 6H).

According to the analysis of related databases, 501420-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
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Synthetic Route of 623-03-0, 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 623-03-0 as follows.

Under a nitrogen atmosphere, a reaction vessel of 20 ml in volume was charged with bis(pinacolate)diboron (1.1 Ig (4.4 mmol)), degassed methanol (7.2 g) and diisopropylethylamine (1.13 g (8.7 mmol)) and stirred at room temperature. The reaction vessel was charged with bis(l,5-cyclooctadiene)nickel (32 mg (0.12 mmol)), triphenylphosphine (61 mg (0.23 mmol)), and 4-chlorobenzonitrile (0.40 g (2.9 mmol)) and stirred at 3O0C for 21 hours, and thereafter stirred at 500C for 3 hours. The reaction solution was analyzed by gas chromatography. As a result, 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzonitrile was contained in an amount of 0.58 g(2.6 mmol, yield: 88%).

According to the analysis of related databases, 623-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; GENENTECH, INC.; MIKI, Takashi; SHIMASAKI, Yasuharu; BABU, Srinivasan; CHENG, Zhigang; REYNOLDS, Mark, E.; TIAN, Qingping; WO2010/110782; (2010); 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. 455-18-5, name is 4-(Trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H4F3N

Reaction Scheme 3, Step 1 4-Trifluoromethylphenyl-amidoxime A solution of 4-trifluoromethyl benzonitrile (Avocado 14514, 15 g) in toluene (200 ml) was treated with methanol (15 ml) followed by hydroxylamine hydrochloride (2.25 g) and potassium tert-butoxide (3.52 g). The mixture was heated to 80 C. and treated with further portions of hydroxylamine hydrochloride (1.07 g) and potassium tert-butoxide (3.52 g) after 2, 4 and 6 h. The mixture was stirred for 16 h, and then cooled. The solvents were evaporated and the residue partitioned between water (100 ml) and dichloromethane (200 ml). The aqueous layer was extracted with two further portions of dichloromethane (2*200 ml). The organic solutions were combined, dried (anhydrous magnesium sulphate), filtered and evaporated to give the title compound as a white solid (16.7 g, 93%). Mass spectrum, 215 [M+H]+.

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Edlin, Christopher David; Redshaw, Sally; Smith, Ian Edward David; Walter, Daryl Simon; US2003/69276; (2003); A1;,
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Synthetic Route of 105-34-0, 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. 105-34-0, name is Methyl 2-cyanoacetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

97 g (0.56 mol) of 1-nitronaphthalene,166.5 g (1.68 mol) of methyl cyanoacetate,40.1 g (0.62 mol) of potassium cyanide,62.9 g (1.12 mol) of potassium hydroxide,And the mixture was stirred.Dimethylformamide 970 mLAnd the mixture was stirred overnight at 60 C.After the solvent was removed by concentration under reduced pressure at room temperature, 10%500 mL of an aqueous solution of sodium hydroxide was added and the mixture was refluxed for about 1 hour.After separation by column chromatography, recrystallization from toluene and heptane gave 50.8 g of intermediate 4-a. (Yield: 54%)

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, Methyl 2-cyanoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SFC Ltd.; Choi Yeong-tae; Lee Se-jin; Park Seok-bae; Ryu Tae-jeong; Yang Byeong-seon; Lee Da-jeong; (92 pag.)KR2018/10087; (2018); A;,
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Reference of 75279-53-7, A common heterocyclic compound, 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, molecular formula is C8H5ClFN, 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.

Reagents and conditions: (a) EtONa, EtOH, refluxing; (b) CH3NHNH2, HC1, EtOH, IVIW, 100C, 40 mm; (c) 2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)acetic acid,Mukaiyama?s reagent, TEA, DCM, THF, MW, 75C, 30 mm. A mixture of 1.8 ml (15mmol) of ethyl 2,2,2-trifluoroacetate (ib) and 1.2 g (7.1 mmol) of 2-(4-chloro-2-fluorophenyl)acetonitrile (la) in 10 ml of ethanol was slowly dropped into hot solutionof 1.2 g of sodium in 20 ml of ethanol. The mixture was refluxed overnight. Thesolution turns red. After cooled down, the solution was poured into 250 ml of cold wateracidified with 10 ml concentrated HC1. The mixture was extracted with ethyl acetate.The ethyl acetate extraction was washed with water, brine and dried over MgSO4. Ethylacetate was removed and the residual reddish oil of 2-(4-chloro-2-fluorophenyl)-4,4,4-trifluoro-3-oxobutanenitrile (ic) was obtained in 1.2 g. The raw material was dissolvedin 10 ml of ethanol and used in next step without further purification. A mixture of 2 mlof the above ethanol solution and 72 tl of methylhydrazine with 0.14 ml ofconcentrated HC1 was irradiated in microwave oven at 100C for 40mm. The solutionwas treated with saturated NaHCO3 and extracted by ethyl acetate. The organic layerwas washed with water, brine, dried over MgSO4 and concentrated. The yellow residuewas subjected to flash chromatography purification with MeOHIDCM to give 120 mgof 4-(4-chloro-2-fluorophenyl)-3 -(trifluoromethyl)- 1-methyl-i H-pyrazol-5 -amine (id)as light yellow solid. M/Z = 294.6 (M+i). To a mixture of 2-(2-isopropyl-1H-benzo[d]imidazol-i-yl)acetic acid (0.16 mmol, from ChemBridge) and Mukaiyama?sreagent (0.38 mmol) in 1.5 ml anhydrous DCM, 4-(4-chloro-2-fluorophenyl)-3-(trifluoromethyl)- i-methyl-i H-pyrazol-5 -amine (1 d, 0.12 mmol) obtained as described above, triethylamine (0.40 mmol) and 0.5 ml of anhydrous THF were added. The mixture was vortexed and subject to microwave irradiation for 30 mm at 75C to give a deep green clear solution. Then 80 ml of ethyl acetate was added and washed with 80 ml of saturated NaHCO3 twice, brine and dried over MgSO4. After solvent removal andpurification on a flash chromatography, slightly brown color solid was obtained. After recrystallization in ethyl acetate/hexane, 45 mg of Compound (1) was given as white powder solid. ?HNMR (500 MFIz, MeOD) 7.79 (d, J = 7.7 Hz, 1H), 7.62 (dt, J = 15.8, 8.2 Hz, 3H), 7.36 – 7.15 (m, 3H), 5.55 (s, 2H), 3.89 (s, 3H), 3.55 – 3.44 (m, 1H), 1.47 (d, J = 6.9 Hz, 6H); M/Z =494.9 (M+1).

The synthetic route of 75279-53-7 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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63089-50-9, name is 4-Methylphthalonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H6N2

General procedure: A 50 mL round bottom flask equipped with a reflux condenser was charged with the appropriate amount of the substituted phthalonitrile (4.0 mM), zinc triflate (5.0 M%, 0.20 mM), and chlorobenzene (30 mL) under argon. The mixture was stirred to dissolve the phthalonitrile and then 2-aminoalcohol (8.0 mM), dissolved in dry chlorobenzene, was slowly added. The temperature was raised to 135 C and the reaction mixture was refluxed for 24 h. The product of the reaction, which was obtained as an oily residue, was dissolved in 30 mL of dichloromethane and then extracted twice with distilled water (20 mL). The aqueous layer was separated and washed with dichloromethane. The separated organic layers were dried using anhydrous sodium sulfate. The dichloromethane was removed under vacuum on a rotary evaporator to give the crude product, which was then purified using silica gel column chromatography with dichloromethane/ether (4/1) as eluent [14, 16, 17].

The synthetic route of 63089-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ibrahim, Mansur B.; Shakil Hussain; Fazal, Atif; Fettouhi, Mohammed; El Ali, Bassam; Journal of Coordination Chemistry; vol. 68; 3; (2015); p. 432 – 448;,
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Related Products of 628-20-6,Some common heterocyclic compound, 628-20-6, name is 4-Chlorobutyronitrile, molecular formula is C4H6ClN, 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.

General procedure: A mixtureof aziridine 1 (0.25 mmol), nitrile 2 or 4 (0.25 mmol) and perchloric acid(0.25 mmol) was placed in a mortar. The reaction mixture was thoroughlyground at room temperature for 5 min. After completion (TLC) the reactionmixture was diluted with a 1 : 1 water/ethyl acetate mixture (10 ml) andwashed with sodium bicarbonate (10 ml) followed by brine solution (10 ml).Then the combined organic layer was dried over anhydrous Na2SO4.Evaporation of solvent furnished the crude product which was subjectedto column chromatography using ethyl acetate-light petroleum as eluentto obtain the analytically pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chlorobutyronitrile, its application will become more common.

Reference:
Article; Charushin, Valery N.; Chupakhin, Oleg N.; De, Aramita; Kopchuk, Dmitry S.; Kovalev, Igor S.; Majee, Adinath; Santra, Sougata; Zyryanov, Grigory V.; Mendeleev Communications; vol. 30; 2; (2020); p. 188 – 189;,
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Electric Literature of 56043-01-7, These common heterocyclic compound, 56043-01-7, name is 2-Amino-6-methylbenzonitrile, 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 mixture of 6-chloro-N-(4-fluoro-benzyl)-4-isopropyl-nicotinamide (Description 6) (100 mg), 2- amino-6-methyl-benzonitrile (43 mg), cesium carbonate (168mg), tris (dibenzylideneacetone) dipalladium (0) (ex-Aldrich, 3.36mg) and 4,5-bis (diphenylphosphino) – 9,9-dimethylxanthene (ex-Aldrich, 2.3 mg) and 1,4-dioxan (1 ml) was heated to relux under nitrogen for 24h. When cool, the mixture was diluted with ethyl acetate and filtered through a PTFE disc (1.0 M) disc and the filtrate evaporated. The residue was purified using the Biotage Horizon HPFC System and the resultant product was triturated with ether, washed with ether, and dried in vacuo at 40 to give 6- (2-cyano-3-methyl-phenylamino)-N-(4-fluoro-benzyl)-4-isopropyl- nicotinamide (15mg). NMR (d6-DMSO) 8 1.16 (6H, d), 2.46 (3H, s), 3.35-3. 45 (1H, m), 4. 36-4. 47 (2H, m), 6.95 (1H, s), 7.08 (1H, d), 7.13 (1H, t), 7. 35 (2H, m), 7. 39 (2H, t), 7.68 (1H, d), 8.07 (1H, s), 8.9 (1H, m), 9.14 (1H, s). LC/MS t = 3. 27min, [MH+] 403 consistent with molecular formula C24H23FN40

The synthetic route of 56043-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DOUGHTY, Jennifer, Margaret; WO2005/74939; (2005); A1;,
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