Month: May 2021

Reference of 3100-67-2, The chemical industry reduces the impact on the environment during synthesis 3100-67-2, name is 1-Amino-2-naphthonitrile, I believe this compound will play a more active role in future production and life.

The mixture was stirred into 200 mL of tetrahydrofuran and <9-a>, obtained from scheme 21, 25.0 g (149 mmol), phenyl magnesium bromide (3.0 M in Et2O) 87.4 mL (297 mmol) was added dropwise at 0 C and refluxed for about one hour. Ethyl chloroformate 19.4 g (179 mmol) was added dropwise and it was refluxed for about 1 hour. Then aqueous solution of ammonium chloride was added and then washed with water and heptane to give <9-b> 32.4 g (80% yield).

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, 1-Amino-2-naphthonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SFC Co. Ltd.,; Yoo, Se Jin; Lee, Se Jin; (64 pag.)KR101554545; (2015); B1;,
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Related Products of 1123172-88-2, 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. 1123172-88-2, name is 3,5-Difluoro-4-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 250 ml stainless steel autoclave, 120 g of N,N-dimethylformamide and 18.5 g (0.1 mol) of 3,5-difluoro-4-nitrobenzonitrile were added.15.0 g of potassium carbonate, 6.0 g (0.1 mol) of isopropylamine, sealed in an autoclave, stirred at 60 to 65 C for 5 hours, cooled to 20 to 25 C, the material was removed, filtered, and the filtrate was evaporated under reduced pressure to give a solvent. To 25 C,Add 20 g of methyl tert-butyl ether, filter, and dry.20.7 g of 3-fluoro-4-nitro-5-isopropylaminobenzonitrile (II) were obtained.The yield was 92.8%, and the liquid phase purity was 99.5%.

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, 3,5-Difluoro-4-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Liu Yuesheng; Zhu Chengchen; Zhang Mingfeng; Wang Tao; (14 pag.)CN110218189; (2019); A;,
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Electric Literature of 1528-41-2, 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. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 1.0 g of 3,3-dimethylcyclohexanone (S6; 7.9 mmol), hydroxylamine hydrochloride (0.66 g,9.5 mmol), 10 mL of ethanol, and 1.6 g of K2CO3 (12 mmol) was heated to 70 C for 64 hours. Themixture was concentrated suspended in 10 mL of water, the extracted three times each with 30 mL ofEtOAc. The extracts were combined and concentrated to provide 1.2 g of 3,3-dimethylcyclohexanoneoxime (S7) that was used crude. To a 0 C solution of S7 (0.20 g, 1.4 mmol) in 2 mL of THF was added dropwise 1.6 M BuLi in hexanes(1.8 mL, 2.8 mmol). The mixture stirred for 30 minutes at room temperature, then ethyl 2-(4-cyanophenyl)acetate (0.27 g, 1.4 mmol) was added. After stirring for 1 hour, 0.7 mL of concentratedH2SO4 was added. After stirring for 1 hour, 25 mL of water was added and the mixture was extractedthree times each with 15 mL of EtOAc. The extracts were concentrated and the residue was purified firstby silica chromatography (0-50% EtOAc in heptanes), then by preparative HPLC (C18 column 10-90%MeCN in H2O, both 0.1% v/v formic acid) or give 41 mg of 16.

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, Ethyl 2-(4-cyanophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meyers, Kenneth; Cogan, Derek A.; Burke, Jennifer; Arenas, Raquel; Balestra, Michael; Brown, Nicholas F.; Chen, Zhidong; Cerny, Matthew A.; Clifford, Holly E.; Colombo, Federico; Fader, Lee; Frederick, Kosea S.; Guo, Xin; Goldberg, Daniel; Hornberger, Keith R.; Kugler, Stanley; Lord, John; Marshall, Daniel R.; Moss, Neil; Parmentier, Jean-Huges; Richman, Jeremy R.; Schmenk, Jennifer; Weldon, Steven M.; Yu, Maolin; Zhang, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 979 – 984;,
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These common heterocyclic compound, 19295-57-9, name is 3-Hydroxy-2,2-dimethylpropanenitrile, 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. HPLC of Formula: C5H9NO

N,N-dimethylformamide (55 ml) was added to a tetrahydrofuran (330 ml) of 10.9 g (0.11 mol) of 3-hydroxy-2,2-dimethylpropionitrile (I-72), and 5.3 g (0.132 mol) of sodium hydride was added thereto under ice-cooling and then stirred at room temperature for 30 minutes. This was again ice-cooled, 19.6 ml (0.165 mol) of benzyl bromide and 4.1 g (11.0 mmol) of tetra-n-butylammonium iodide were added thereto and then stirred overnight while raising the temperature to room temperature. The reaction solution was mixed with saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and then dried over magnesium sulfate, and the solvent was evaporated. The thus obtained residue was applied to a silica gel column chromatography, and 20.0 g (96%) of the title compound was obtained as a colorless oily substance from a n-hexane-ethyl acetate (9:1 v/v) eluate. 1H-NMR (CDCl3)delta: 1.36 (6H, s), 3.38 (2H, s), 4.62 (2H, s), 7.29-7.37 (5H, m).

The synthetic route of 3-Hydroxy-2,2-dimethylpropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); A1;,
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Application of 143879-78-1, These common heterocyclic compound, 143879-78-1, name is 3-Amino-2,6-difluorobenzonitrile, 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.

Methyl (3 S)-3 ,7-dimethyl- 1,1 -dioxo-2,3 ,4,5 -tetrahydropyrrolo [3 ,4-f]thiazepine-6- carboxylate (200 mg, 0.73 mmol) and 3-amino-2,6-difluoro-benzonitrile (0.16 g, 0.88 mmol) in dry THF (5 mL) was treated with lithium bis(trimethylsilyl)amide (2.2 mL, 1 M in THF, 2.2 mmol) and this was stirred overnight at room temperature. Theresulting mixture was quenched with NH4C1 (aq., sat., 5 mL). Then 5 mL of brine wasadded and the layers were separated. The water layer was extracted using EtOAc (2 X30 mL). The combined extracts were concentrated in vacuo and the obtained crude waspurified using silica gel column chromatography (gradient elution: EtOAc:heptane0:100 to 100:0). The desired fractions were concentrated in vacuo and the obtainedresidue was purified via preparative HPLC (Stationary phase: RP XBridge Prep C18 OBD-l0jim, 3OxlSOmm, Mobile phase: 0.25% NH4HCO3 solution in water, ACN). The desired fractions were concentrated under reduced pressure, co-evaporated with methanol (2 X 25 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 157 (7.6 mg). ?H NMR (400 MHz, DMSO-d6) oe ppm 1.14 (d, J=6.82 Hz,3H)1.31-1.45(m,1H)1.81-1.91(m,1H)2.77-2.89(m,1H)3.07-3.18(m,1H)3.58 – 3.67 (m, 1 H) 3.70 (s, 3 H) 7.03 (d, J=9.68 Hz, 1 H) 7.40 – 7.51 (m, 2 H) 8.06(td,J=8.97, 6.05 Hz, 1 H) 10.31 (s, 1 H); Method B; Rt: 0.85 mi mlz :393 (M-H)Exact mass: 394.1, MP: 247.5 C.

The synthetic route of 143879-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VENDEVILLE, Sandrine, Marie, Helene; LAST, Stefaan, Julien; DEMIN, Samuel, Dominique; GROSSE, Sandrine, Celine; HACHE, Geerwin, Yvonne, Paul; HU, Lili; PIETERS, Serge, Maria, Aloysius; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; (244 pag.)WO2017/1655; (2017); A1;,
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Application of 19295-57-9, 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 19295-57-9 as follows.

Preparation No.6: 3-Methoxy-2,2-dimethylpropylamine HCl; To a mixture of sodium tetrahydroborate (7.4 g, 200 mmol) in EtOH (100 mL) at about 0 0C was added cyanodimethylacetic acid ethyl ester (TCI, 10.0 g, 70.8 mmol) in EtOH (100 mL) over about EPO 45 min. The mixture was allowed to warm to ambient temperature over about 30 min. After about 60 h, the solvents were removed in vacuo. The resulting material was treated with saturated aqueous NH4Cl (150 mL) and extracted using DCM (3 x 30 mL). The combined organic layers were dried over Na2SO4 and concentrated to yield the crude 3-hydroxy-2,2-dimethylpropionitrile (8.61 g). A mixture of crude 3-hydroxy-2,2-dimethyl-propionitrile (1.0 g, 10 mmol) in DCM (40 mL) was treated with tetrafluoroboric acid (1.4 g, 10 mmol) followed by 2 M trimethylsilyldiazomethane in heptane (5.0 mL, 10 mmol) at about 0 0C over about 10 min. The mixture was treated with additional 2 M trimethylsilyldiazomethane in heptane (2 mL, 4.0 mmol) after about 20 min, followed by additions of 2 M trimethylsilyldiazomethane in heptane (1.3 mL, 2.6 mmol) and 2 M trimethylsilyldiazomethane in heptane (1.3 mL, 2.6 mmol) after about 20 min intervals sequentially. The mixture was allowed to stir at about 0 0C for about 50 min before it was poured slowly over water. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were washed with water, dried over Na2SO4, and concentrated to yield the crude 3- methoxy-2,2-dimethylpropionitrile as a yellow oil (1.2 g). Into a Parr shaker vessel was added crude 3-methoxy-2,2-dimethylpropionitrile (1.0 g, 8.8 mmol), 33% aqueous ammonium hydroxide (75 mL), MeOH (10 mL), and 8.0 M Raney nickel in water (1 mL, 8.0 mmol). The materials were charged with hydrogen and shaken at ambient temperature. After about 16 h, the mixture was filtered over Celite and treated with 5 M sodium hydroxide in water (2 mL), di-tert- butyldicarbonate (2.3 g, 11 mmol), and EtOAc (75 mL). After about 5 h, the layers were separated and the aqueous layer was washed with DCM. The combined organic layers were washed with water then dried over Na2SO4 and concentrated in vacuo. The residue was purified via FCC using EtO Ac/heptane (1:4). The fractions containing product, as visualized on TLC with ninhydrin stain, were concentrated in vacuo to yield (3-methoxy-2,2-dimethylpropyl)-carbamic acid tert-butyl ester, which was treated with 1.25 M HCl in methanol (1 mL) at ambient temperature. After about 2 h, the mixture was concentrated in vacuo to give methoxy-2,2-dimethylpropylamine HCl: (0.090 g): 1H NMR (DMSO-d6, 400 MHz) 6 3.85-3.75 (2H), 3.26 (3H), 3.13 (2H), 2.65-2.70 (2H), 0.91 (6H); TLC (acetone/MeOH 95:5) Rf = 0.2.

According to the analysis of related databases, 19295-57-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/28051; (2007); A2;,
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Reference of 500912-18-5, 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 500912-18-5 as follows.

A mixture of 6-chloro-4-(ethyl amino) nicotinaldehyde (Scheme 1 compound 6) (1.7 g, 9.32 mmol), Scheme 56 compound 4 (2.0 g, 12.11 mmol) and K2C03 (3.8 g, 27.96 mmol) in dry DMF (10 mL) was heated to 100 C under nitrogen atmosphere for 16 h. After TLC showed the starting material was completely consumed, the reaction mixture was cooled to RT, diluted with EtOAc (2 x 50 mL), washed with water (2 x 20 mL) and brine (10 mL) then dried over Na2S04 and concentrated to give a residue which was purified by flash chromatography on silica gel (eluting with petroleum ether/EtOAc 100/0 gradually increasing to 60/40) to give 7-chloro-l-ethyl-3-(2-fluoro-6-methoxyphenyl)-l,6-naphthyridin-2(lH)- imine (800 mg, 26%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 8.41 (s, 1H), 7.51 (q, J= 8.0 Hz, 1H), 7.41 (d, J= 10.6 Hz, 2H), 7.07-6.92 (m, 2H), 4.26 (m, 2H), 3.77 (d, J = 2.4 Hz, 3H), 1.22-1.16 (m, 3H). MS [ESI, MH+] = 332.09.

According to the analysis of related databases, 500912-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
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Application of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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.

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (5.0 g, 22.9 mmol) and potassium carbonate (9.5 g, 68.8 mmol) in N,N-dimethylformamide (45.9 ml) was added (S)-1 ,1 ,1 – trifluoropropanol [CAS 3539-97-7] dropwise (2.88 g, 25.2 mmol). The resulting mixture was heated at 55 “C for for 15 hours and cooled to room temperature. Water (100 ml) was added to the mixture and extracted with diethyl ether (3chi50 ml). The combined organic extracts were sequentially washed with water (2chi100 ml), brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an off white solid (6.93 g). The residue was purified by flash column chroamtography to give the ether as a white crystalline solid (5.90 g, 97 % purity, 80 %).LC-MS (method A): R, = 1 .29 min; MS (ESIpos): m/z = 312.0 [M+H]+1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1 .51 1 (4.41 ), 1.531 (15.64), 1 .533 (16.00), 1 .548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1 .01 ), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

The synthetic route of 133541-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUENTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David B; FERRARA, Steven, James; LIU, Kery; HERBERT, Simon, Anthony; MERZ, Claudia; NIEHUES, Michael; NISING, Carl, Friedrich; SCHAeFER, Martina; ZIMMERMANN, Katja; KNAEBLEIN, Joerg; THEDE, Kai; FAUPEL, Thomas; (539 pag.)WO2018/77944; (2018); A2;,
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Application of 69975-66-2, 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. 69975-66-2, name is 3-Oxo-indan-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a series of 1.5 mL glass tubes was added amine 5 or 6 in NMP (0.95 M, 0.095 mmol), followed by solutions of different indanones (0.5 M, 0.1 mmol) in NMP, and these mixtures were subsequently treated with acetic acid (0.1 mmol), followed by 5-ethyl-2-methylpyridineborane (PEMB) (0.2 mmol). The reaction mixture was heated at 65 C on a reaction block for 24 h. The reaction mixtures were purified directly using an automated mass-guided reverse phase HPLC, and product containing fractions were concentrated to give final products of >90% purity as judged by LC-MS (average of 220 and 254 nm traces).

The chemical industry reduces the impact on the environment during synthesis 3-Oxo-indan-5-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Vilums, Maris; Zweemer, Annelien J. M.; Barmare, Farhana; Van Der Gracht, Anouk M. F.; Bleeker, Dave C. T.; Yu, Zhiyi; De Vries, Henk; Gross, Raymond; Clemens, Jeremy; Krenitsky, Paul; Brussee, Johannes; Stamos, Dean; Saunders, John; Heitman, Laura H.; Ijzerman, Adriaan P.; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 121 – 134;,
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Reference of 6283-71-2, 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. 6283-71-2, name is Dimethyl 2-cyanosuccinate, This compound has unique chemical properties. The synthetic route is as follows.

Cyanodiester 12 (1.16 g; 6.78 mmol) was dissolved in ethanol/water 1:1 (12 mL), cooled to 0-5 C and Et3N (1.2 mL) was added dropwise. After 15 min tert-butyl acrylate (1.05 mL; 0.92 g; 7.14 mmol) was added dropwise. The mixture was stirred at 0-5 C for 1.5 h, allowed to warm to room temperature and stirred for further 2 h. It was then concentrated, diluted with water, acidified with 2 N HCl to pH 4 and extracted 3* with AcOEt. The combined organic extracts were dried with MgSO4, concentrated in vacuo and chromatographed on silica gel in hexane/AcOEt (4:1) to give 20 (0.61 g; 29%; Rf 0.27) and 21 (0.77 g; 38%; Rf 0.23) as colourless oils.

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-cyanosuccinate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Weinberg, Kamil; Stoit, Axel; Kruse, Chris G.; Haddow, Mairi F.; Gallagher, Timothy; Tetrahedron; vol. 69; 23; (2013); p. 4694 – 4707;,
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