Tag: M.W=100-200

Application of 1247885-40-0,Some common heterocyclic compound, 1247885-40-0, name is 2,3-Difluoro-5-nitrobenzonitrile, molecular formula is C7H2F2N2O2, 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.

5-amino-2,3-difluorobenzonitrile (0273) To a solution of 2,3-difluoro-5-nitrobenzonitrile (920 mg, 5.00 mmol) in acetonitrile (25 mL) was added iron powder (1.96 g, 35.10 mmol) and acetic acid (6.0 g, 99.91 mmol). The resulting mixture was stirred for 2 h at room temperature and the solid that formed in the reaction mixture were removed by filtration. The filtrate was diluted with water (100 mL) and the pH value of the mixture was adjusted to 8 with saturated sodium bicarbonate solution. The resulting mixture was extracted with ethyl acetate (150 mL×2) and the organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by a neutral alumina column with ethyl acetate in hexane (0% to 65% gradient) to yield 5-amino-2,3-difluorobenzonitrile as yellow solid (660 mg, 86%).

The synthetic route of 1247885-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
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Reference of 17417-09-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17417-09-3 name is 2-Fluoro-5-nitrobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-Morpholin-4-yl-5-nitro-benzonitrile 3-Cyano-4-fluoronitrobenzene (3.3 g, 19.9 mmol) was dissolved in ethyl acetate (10 mL). Morpholine (2.2 mL, 25 mmol), and N,N-diisopropylethylamine (3.5 mL, 20 mmol) were added and the mixture stirred overnight at room temperature. At 17 h, additional ethyl acetate (150 mL) was added and the combined mixture was washed with water (50 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/87575; (2004); A1;; ; Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
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Related Products of 25808-30-4,Some common heterocyclic compound, 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, molecular formula is C3H7ClN2, 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.

Step 1 To a solution of 3-(4-fluorobenzoyl)-2-pyridinecarboxylic acid (19.8 g) in dichloromethane (200 ml) were added thionyl chloride (29.1 ml) and DMF (one drop). The mixture was stirred for 4 hours at room temperature. The solvent was distilled off, and the residue was dissolved in dichloromethane (100 ml). This solution was added to a mixture of N-methylaminoacetonitrile hydrochloride (9.46 g), triethylamine (33.7 ml) and dichloromethane (150 ml), which was stirred for 16 hours at room temperature. The solvent was distilled off. To the residue was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with an aqueous solution of sodium hydrogencarbonate and water, which was then dried, followed by distilling off the solvent to leave N-cyanomethyl-3-(4-fluorobenzoyl)-N-methyl-2-pyridinecarboxamide (22.8 g). NMR(200 MHz,CDCl3) ppm: 3.16(3H*1/3,s), 3.21(3H*2/3,s), 4.44(2H*2/3,s), 4.55(2H*1/3,s), 7.17(2H,t,J=8.4 Hz), 7.50(1H,m), 7.85(3H,m), 8.75(1H,dd,J=1.6,4.8 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Methylamino)acetonitrile hydrochloride, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5585385; (1996); A;,
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Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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.

N-(4-Cyano-2-methoxyphenyl)formamide Acetic anhydride (0.65 mL, 6.7mmol) was cooled in an ice bath and formic acid (0.38 mL, 10 mmol) was added with stirring. The ice-bath was removed and the mixture was stirred for a further 60 minutes. The reaction was re-cooled in the ice-bath and 4- amino-3-methoxybenzonitrile (0.25 g, 1.58 mmol) was added. The reaction was stirred at ice-bath temperature for 5 minutes, then at room temperature for 60 minutes. The reaction was concentrated in vacuo, azeotroped with toluene and the title compound was precipitated from ether/hexanes as a white powder (255 mg, 71.3%). 1 H NMR (500 MHz, DMSO-d6): delta 10.07 (s, 1 H), 8.39 (s, 1 H), 8.37 (s, 1 H), 7.52 (d, J = 1.7 Hz, 1 H), 7.4 (dd, J = 8.4, 1 .8 Hz, 1 H), 3.92 (s, 3H). LCMS (ESI) R, = 1 .76 minutes MS m/z 177 [M+H]+

The synthetic route of 177476-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
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24973-49-7, name is [1,1′-Biphenyl]-2-carbonitrile, 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

General procedure: A stirring suspension of lithium aluminum hydride (1.1equiv) in anhydrous THF was treated dropwise under N2 with a solution of aluminum chloride (0.9equiv) in THF. The reaction mixture was maintained at room temperature during the addition by means of a water bath. After addition was complete, the reaction mixture was stirred vigorously for 20min and then cooled to 0C before adding dropwise a solution of biphenyl-2-carbonitrile 4 (1.0equiv) in THF. After complete addition, stirring was continued for 2h and the reaction was quenched by slowly adding methanol followed by water. The mixture was concentrated under reduced pressure, and the residue was extracted with 1N HCl. The aqueous phase were combined, washed with EtOAc and neutralized by addition of 10N NaOH. The mixture was extracted with CH2Cl2, the organic phase was combined, washed with water, dried over Na2SO4 and evaporated under reduced pressure. The residue was filtered through a pad of silica gel, and the filtrate was evaporated and dried to give the product 5 in 60-75% yields. 4.3.1 Biphenyl-2-ylmethanamine (5-1) The reaction of lithium aluminum hydride (2.15 ml, 2.15 mmol) in anhydrous THF, aluminum chloride (234 mg, 1.76 mmol), and biphenyl-2-carbonitrile (350 mg, 1.95 mmol) in THF (5 ml) gave the title compound 5-1 (256 mg, 1.40 mmol, 72% yield). 1H NMR (400 MHz, CDCl3) delta 7.46 (d, J = 7.5 Hz, 1H), 7.41-7.40 (m, 2H), 7.37-7.32 (m, 3H), 7.30 (td, J = 7.5, 1.3 Hz, 1H), 7.24 (dd, J = 8.1, 2.1 Hz, 1H), 3.81 (s, 2H), 1.34 (s, 2H).

The synthetic route of 24973-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Youngjae; Tae, Jinsung; Lee, Kangho; Rhim, Hyewhon; Choo, Il Han; Cho, Heeyeong; Park, Woo-Kyu; Keum, Gyochang; Choo, Hyunah; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4587 – 4596;,
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Synthetic Route of 1897-52-5,Some common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

4-(2-Cyano-3-fluorophenyl)piperazine-l-carboxylic acid tert-butyl ester. In a round bottom flask, sodium hydride (60%) (2.40 g; 60 mmol) was suspended in DMF (25 mL) and cooled in an ice water bath under nitrogen. 1-Boc- Piperazine (9.53 g; 50.6 mmol) was added in small portions to the reaction mixture at 0 C over 30 minutes. The mixture was allowed to stir at room temperature for 3 hours and the recooled to 0 C. 2,6-Difluorobenzonitrile (8.57 g; 60 mmol) was added to the reaction mixture in DMF (10 mL) over 45 minutes. The mixture was stirred at room temperature for 16 hours. The reaction mixture was poured in ice water (250 mL) and stirred. The solid was collected by vacuum filtration and washed with water. And then dried under vacuum to yield the title compound (11.65 g; 75% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; deCODE Chemistry, Inc.; WO2008/16973; (2008); A1;,
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Application of 7357-70-2, 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. 7357-70-2, name is 2-Cyanothioacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 12A (S)-2-Amino-4-{4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}-6-mercaptopyridine-3,5-dicarbonitrile 1.52 g (6.43 mmol) of the compound from Example 11A, 1.29 g (12.9 mmol) of cyanothioacetamide and 1.3 g (12.9 mmol) of 4-methylmorpholine are dissolved in 15 ml of ethanol, and the mixture is stirred under reflux for 3 h. The mixture is then stirred at RT for 18 h. The reaction solution is concentrated using a rotary evaporator, and the residue is chromatographed on silica gel 60 (mobile phase: dichloromethane/ethanol 10:1). Yield: 1.06 g (43% of theory) LC-MS (Method 3): Rt=1.75 min; MS (ESIpos): m/z=383 [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-Cyanothioacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer HealthCare AG; US2008/269300; (2008); A1;,
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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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Fluoro-5-nitrobenzonitrile

General procedure: General procedure: 3-Hydroxy oxetane (370 mg, 5 mmol, 2 equiv) in THF (15 ml) under argon gas, was cooled to 0 C. Potassium tert-butoxide (617 mg, 5.5 mmol, 2.2 equiv) was added in one portion, and the reaction mixture was stirred for 20 minutes at 0 C. Then 2-fluoro-5-nitrobenzonitrile (415 mg, 2.5 mmol, 1 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0 C and allowed to warm up to ambient temperature over 1 hour. The reaction mixture was concentrated, and the residue was taken in DCM and water. The layers were separated, and the organic layer was washed with water (x2), dried over Na2S04, filtered, and concentrated to provide 5-nitro-2-(oxetan- 3-yloxy)benzonitrile (495 mg, 90%) as a brown-yellow solid that was used without further purification. [00576] 1H NMR (300 MHz; 6-DMSO) delta 8.74-8.75 (m, 1H), 8.42-8.47 (m, 1H), 7.09- 7.12 (dd, 1H, J = 0.9Hz, J = 9.3Hz), 5.56-5.63 (m, 1H), 4.96-5.00 (m, 2H), 4.59-4.63 (m, 2H); m/z = 221 (M+H)+.

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 17417-09-3.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
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Electric Literature of 64248-62-0, 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. 64248-62-0, name is 3,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of terf-butyl-(S)-3-hydroxypyrrolidine-l-carboxylate (4.44 g, 23.7 mmol) in N,N- dimethylformamide (40 mL), sodium hydride (1.72 g, 43.1 mmol) was added under nitrogen atmosphere at 0 C and stirred for 30 min. To the resulting reaction mixture, 3,4-difluorobenzonitrile (3 g, 21.6 mmol) in /V, /V-di methylformam ide (10 mL) was added slowly at 0 C and stirred at 25 C for 2 h. The reaction mixture was quenched with ammonium chloride solution and diluted with ethyl acetate (100 mL). The dichloromethane layer was collected and washed twice with water (80 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash column chromatography on silica gel by eluent 50% ethyl acetate in hexane to obtain tert- butyl (S)-3-(4-cyano-2-fluorophenoxy)pyrrolidine-l-carboxylate (5.3 g, 17.3 mmol, 80% yield).

The synthetic route of 3,4-Difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PI INDUSTRIES LTD.; BHUJADE, Paras Raybhan; NAIK, Maruti N; PAWAR, Rajesh; TRIVEDI, Pooja; DENGALE, Rohit Arvind; KULKARNI, Shantanu Ganesh; TEMBHARE, Nitin Ramesh; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander G.M.; (172 pag.)WO2020/70610; (2020); A1;,
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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. 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Fluoro-2-(trifluoromethyl)benzonitrile

General procedure: Sixty per cent NaH in oil was washed with hexane and then added to a stirred solution of phenothiazine 5 or phenoxazine 6 derivative (10.0mmol) in dry THF (15mL) under a nitrogen atmosphere at room temperature. After stirring for 30min, 4-fluoro-2-(fluoromethyl)-benzonitrile 7 was added. (0007) The reaction mixture was quenched with water (30mL). The organic phase was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography using a mixture of hexane/ethyl acetate (3:1) as eluent.

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 194853-86-6.

Reference:
Article; Baraket, Faiza; Pedras, Bruno; Torres, Erica; Brites, Maria Joao; Dammak, Mohamed; Berberan-Santos, Mario N.; Dyes and Pigments; vol. 175; (2020);,
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