Category: nitriles-buliding-blocks

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 64248-64-2 as follows. COA of Formula: C7H3F2N

General procedure: The starting material 1 (7.0 mmol) was dissolved in 40 mL DMSO, and the mixture was heated and kept at 75 C for 20 min under stirring. After that sodium sulfide nonahydrate (10.5 mmol) was added to the solution in batch and the reaction continued under 75 C for 2 h. The reaction was then monitored by TLC and cooled to room temperature. The crude product was further extracted three times by using water and ethyl acetate. The aqueous layer was then adjusted by hydrochloric acid to a pH value of 3-4. Enough water was added and intermediate 2 precipitated out subsequently. The resulting solid 2 was filtered out in 75%-90% yields (Some of them were hard to purify and were used directly for the next reaction). Characterizations for 2 were listed in Table S2.

According to the analysis of related databases, 64248-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Ren-Jun; Zhou, Kai-Xuan; Yang, Haijin; Song, Guo-Qing; Li, Yong-Hong; Fu, Jia-Xin; Zhang, Xiao; Yu, Shu-Jing; Wang, Li-Zhong; Xiong, Li-Xia; Niu, Cong-Wei; Song, Fu-Hang; Yang, Haitao; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 472 – 484;,
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Application of 914637-31-3, 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 914637-31-3 as follows.

4.2 g (181 mmol) of sodium in small pieces were added gradually to a solution of25 g (151 mmol) of(3-fluoro-5-methoxyphenyl)-acetonitrile in 200 mL of diethyl carbonate in such a manner that the temperature remained at approximately 100C.Thereafter, the reaction mixture was heated to reflux for 1 hr. After evaporation under reduced pressure, the mixture was treated with cooled water. The solution was acidifiedwith acetic acid and extracted with EA. The combined organic extracts were dried andevaporated. The residue was purified by silica gel (EA: PE/1 :10) to give 23 g of the title compound as light brown oil (yield: 64%).LC-MS: m/z 238 (M+H); RT=1.72 min/2.5 min.

According to the analysis of related databases, 914637-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; ABBVIE INC.; GENESTE, Herve; OCHSE, Michael; DRESCHER, Karla; JAKOB, Clarissa; WO2014/27078; (2014); A1;,
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Related Products of 1080-74-6, 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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 4 (400 mg, 0.47 mmol) and INCN (458 mg, 2.36 mmol) were dissolved in anhydrous chloroform (CF, 25 mL) and 0.3 mL of pyridine was slowly injected into mixture solution. Thereaction was stirred under a nitrogen atmosphere at 65 C for 12 h. Subsequently, the reaction vessel was cooled to room temperature and extracted with chloroform several times. The extracted organic layer were dried over MgSO4, filtered, and evaporated to obtain a residue. The mixture compound was then purified with column chromatography using chloroform to afford a dark solid. Yield = 275 mg (44%) 1H NMR (300 MHz, CDCl3) delta: 8.87 (s, 2H), 8.69(d, 2H), 8.18 (d, 2H), 7.93 (dd, 2H), 7.89 (dd, 2H), 7.82(m, 4H), 7.77 (dd, 2H), 7.53 (t, 4H), 2.91 (t, 4H), 1.75 (t,4H), 1.25 (m, 4H), 0.82 (t, 6H). 13C NMR (75 MHz,CDCl3) delta: 183.06, 166.92, 164.45, 153.73, 147.76, 142.60,140.51, 139.71, 135.59, 134.57, 132.97, 130.86, 128.93,126.83, 122.33, 122.25, 121.59, 105.02, 102.60, 71.85,61.04, 43.95, 41.65, 31.48, 29.79, 29.13, 27.42, 22.8014.51. Anal. Calcd for C64H54N4S2: C, 78.8; H, 5.6;N,5.7; S, 6.6. Found: C, 78.9; H, 5.5; N,5.6; S, 6.6. MS(MALDI-TOF): m/z [M+] = 974.61 [M+], calcd. 974.37.

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-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lee, Seong Lim; Kim, Hee Su; Ha, Jong-Woon; Park, Hea Jung; Hwang, Do-Hoon; Bulletin of the Korean Chemical Society; vol. 41; 2; (2020); p. 143 – 149;,
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Related Products of 14377-68-5, 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. 14377-68-5, name is 1-Phenylcyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a 1-Phenylcyclobutanemethanamine A commercial suspension of LiAlH4 at 13% in a toluene-THF mixture, under nitrogen (0.595 mole; 175 ml), diluted with 270 ml of THF is maintained at 0 C. A mixture of 90 g (0.572 mole) of 1-phenylcyclobutanecarbonitrile and 800 ml of THF is added dropwise during 20 minutes. After the addition, the temperature is slowly allowed to rise before heating to reflux during 1 hour. After cooling at about 5 C., 150 ml water, 150 ml 10% NaOH and again 560 ml water are poured dropwise with care. The mixture is extracted with ethyl acetate after having saturated the aqueous phase with NaCl. The organic phase is extracted with a N HCl solution. This aqueous phase is made basic by means of 30% NaOH and is extracted with dichloromethane, which, after washing with water, drying over Na2 SO4 and concentration gives a reddish liquid which is purified by distillation. There is obtained 68.65 g (yield=81.3%) of a colorless liquid. b.p.6 =84-92 C. I.R. (film): nu (NH2)=3350 cm-1. N.M.R. (CDCl3): delta=0.9 (2H,s, exchangeable with CF3 COOD); 1.65-2.5 (6H,m); 2.9 (2H,s); 6.8-7.7 (5H,m).

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-Phenylcyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lipha Lyonnaise Industrielle Pharmaceutique; US5387709; (1995); A;,
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Some common heterocyclic compound, 22972-63-0, name is 2-(3,5-Dimethoxyphenyl)-2-methylpropanenitrile, molecular formula is C12H15NO2, 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. Formula: C12H15NO2

PREPARATION E 2-Methyl-2-(3,5-dihydroxyphenyl)-5-phenylpentane To a solution of the Grignard reagent prepared from 2-phenylbromoethane (5.5 g.), magnesium (0.8 g.) and dry ether (60 ml.) is added a solution of 2-methyl-2-(3,5-dimethoxyphenyl)propionitrile (2.75 g.) in dry ether (20 ml.). The ether is distilled off and replaced by dry benzene (50 ml.) and the mixture refluxed for 48 hours. It is then decomposed by careful treatment with dilute sulfuric acid and heated on a steam bath for 1 hour. The mixture is then extracted with ether, the extract dried (MgSO4) and concentrated to an oil. Distillation of the oil in vacuo affords 2-methyl-2-(3,5-dimethoxyphenyl)-5-phenyl-3-pentanone; b.p. 168 C./0.2 mm. (Yield: 2.32 g., 60%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22972-63-0, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4143139; (1979); A;,
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Reference of 846023-24-3, These common heterocyclic compound, 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, 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 49 2E/Z)-2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-methoxy-3-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amino]acrylamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (261 mg, 1.01 mmol) in 5 mL of iso-propanol was added triethylorthoformate (0.504 mL, 3.03 mmol). The mixture was heated to reflux and (4-methoxy-3-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amine (320 mg, 1.06 mmol) in 9 mL of iso-propanol was added dropwise. This mixture was heated at reflux for 25 hours. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with iso-propanol, to provide 465 mg (81%) of (2E/Z)-2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-methoxy-3-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amino]acrylamide as a gray solid, mp 198-199 C.; MS 570.1 (M+H)+. Analysis for C28H29Cl2N5O4-0.2 H2O: Calcd: C, 58.58; H, 5.16; N, 12.20. Found: C, 58.50; H, 5.07; N, 12.07.

Statistics shows that 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide is playing an increasingly important role. we look forward to future research findings about 846023-24-3.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
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Application of 845866-92-4, 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. 845866-92-4, name is 6-Amino-3-bromo-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-amino-5-bromo-6-fluoro-3-nitro-benzonitrileTo a cooled (0 C) solution of 6-amino-3-bromo-2-fluoro-benzonitrile (8.0 g, 37 mmol) in acetonitrile (40 mL) under nitrogen was added dropwise a solution of nitronium tetrafluoroborate in acetonitrile. The reaction mixture and stirred for 16 h at RT. The reaction mixture was treated with brine and extracted with ethyl acetate. The organic fraction was washed with water followed by brine and dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (10 to 20% ethyl acetate:hexanes) afforded 5.0 g (52%) of the title compound. 1 H NMR (300 MHz, CDCI3): delta 8.6 (d, J= 6.9 Hz, 1 H), 6.8 – 7.1 (br. s, 2H).

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, 6-Amino-3-bromo-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; HOMBERGER, Keith, R.; BERGER, Dan, M.; CHEN, Xin; CREW, Andrew, P.; DONG, Hanqing; KLEINBERG, Andrew; LI, An-Hu; MA, Lifu; MULVIHILL, Mark, J.; PANICKER, Bijoy; SIU, Kam, W.; STEINIG, Arno, G.; TARRANT, James, G.; WANG, Jing; WENG, Qinghua; SANGEM, Rajaram; GUPTA, Ramesh, C.; WO2011/100502; (2011); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1141894-75-8, name is 4-(Aminomethyl)-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(Aminomethyl)-3-(trifluoromethyl)benzonitrile

Example 74; (cis)-N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1 ,3,5- triazin-2-yl]amino}cyclohexanecarboxamide; To a solution of 3-{[4-methyl-6-(methylamino)-1 ,3,5-triazin-2- yl]amino}cyclohexanecarboxylic acid (0.100 g, 0.264 mmol) in N,N-Dimethylformamide (DMF) (4 ml) was added 4-(aminomethyl)-3-(trifluoromethyl)benzonitrile (0.053 g, 0.264 mmol) followed by diisopropylethylamine (0.101 ml, 0.580 mmol) and 1 H-1 ,2,3- benzotriazol-1-yloxy-tris(dirnethylamino)-phosphonium hexafluorophosphate (BOP reagent, 0.128 g, 0.290 mmol). The reaction was stirred at room temperature for 4 hours and then purified by preparative HPLC to provide (cis)-N-{[4-cyano-2- (trifluoromethyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1 ,3,5-triazin-2- yl]amino}cyclohexanecarboxamide (83 mg, 0.148 mmol, 56 %). MS (ES) m/e 448[M+H]+. 1H NMR (400 MHz, DMSO-D6) D 7.8 (bs, 1 H), 7.3 (bs, 1 H), 7.2 (m, 1 H), 6.9 (m, 1 H), 3.8 (bs, 2H), 3.3 (bm, 1 H), 2.2 (bm, 4H), 1.8 – 1.5 (bm, 4H), 1.3 – 1.1 (bm, 4H), 0.8 – 0.5 (bm, 4H)

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; SMITHKLINE BEECHAM CORPORATION; WO2009/49157; (2009); A1;,
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Application of 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 3-Cyclopropyl-l-(3-methyl-pyridin-2-yl)-lH-pyrazol-5-amine; To solution of S-cyclopropyl-S-oxo-propionitrile (6.4 g, 46.917 mmol) and N- benzhydrylidene-N’-(3~methyl-pyridin-2-yl)-hydrazine (7.49 g, 26.065 mmol) in ethanol(133 mL) was added p-toluene sulfonic acid (4.958 g, 26.065 mmol) and cone HCl (10 mL).The mixture was heated to reflux under nitrogen for 15 h and then concentrated. The residue was taken up in ethyl acetate (200 mL) and water (100 mL) and solid NaHCO3 added cautiously till there was no more bubbling (due to the formation of CO2 gas). The organic layer was isolated and washed with brine, then dried over Na2SO4 and concentrated. The product was isolated as a pink viscous oil (4.06 g, 40%) by column chromatography (20 %EtOAc in hexanes, then 100 % EtOAc). ES-MS m/z 215.1 (MH+); HPLC RT (min) 1.16{method (A)}.

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

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
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Reference of 1813-33-8, A common heterocyclic compound, 1813-33-8, name is 2-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.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

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:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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