Category: nitriles-buliding-blocks

1080-74-6, Name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 1080-74-6, 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.

Compound 4 (0.15 g, 0.1275 mmol) and 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (0.371 g, 3.825 mmol) were dissolved inchloroform (15 mL). A drop of pyridine was added and the solution wasleft to stir at 65 C overnight. The reaction was dissolved in ethanol andstirred for another 10 min. The product was extracted with dichloromethaneand dried over MgSO4. After removal of the solvent, thecrude product was chromatographically purified on silica gel column(eluted with chlorobenzene) to afford dark purple solid (105 mg, 85%).1H NMR (500 MHz, CDCl3) delta: 8.95 (s, 3H), 8.75 (m, 3H), 8.50 (m, 3H),8.01 (m, 3H), 7.98 (m, 6H), 7.91 (s, 3H), 7.83 (m, 6H), 7.69 (d, 3H),3.04 (m, 6H), 2.28 (m, 6H), 0.95 (m, 36H), 0.62 (m, 30H). 13C NMR (125 MHz, CDCl3) delta: 187.44, 159.75, 159.54, 153.77, 145.88, 145.39,141.05, 139.05, 137.13, 136.97, 135.96, 135.41, 134.29, 133.62,130.51, 124.42, 124.40, 124.27, 123.99, 122.85, 121.62, 119.14,113.53, 113.46, 70.06, 56.40, 37.23, 31.63, 29.57, 24.22, 22.41, 14.02.MS (MALDI-TOF) calculated for C114H108N6O3S3, 1705.77; found,1705.94.

Statistics shows that 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile is playing an increasingly important role. we look forward to future research findings about 1080-74-6.

Reference:
Article; Lin, Kaiwen; Xie, Boming; Wang, Zhenfeng; Xie, Ruihao; Huang, Yunping; Duan, Chunhui; Huang, Fei; Cao, Yong; Organic electronics; vol. 52; (2018); p. 42 – 50;,
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The chemical industry reduces the impact on the environment during synthesis 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, I believe this compound will play a more active role in future production and life. 42872-74-2

General procedure: To 2-bromo-3-methylbenzoic acid (21, 159 g, 739 mmol) in dichloromethane (1000 mL) was added triethylamine (TEA, 119.7 mL, 813 mmol, 1.1 equiv) followed by iso-butyl chloroformate (101.5 mL, 813 mmol, 1.1 equiv) in dichloromethane (DCM, 200 mL) at 0 C over 10 min. Concentrated ammonia water (323 mL) was then added at 0 C over 2 min. The reaction mixture was poured into water (200 mL), cooled to rt and filtered. The solid was washed with water (2 ¡Á 300 mL), 0.5 N HCl (2 ¡Á 150 mL) and dried to give the amide as a solid (120 g, yield 76%). To the solution of the amide obtained (50 g, 233.6 mmol) in DMF (300 mL) was added 2,4,6-trichloro-1,3,5-triazine (64.6 g, 350.4 mmol, 1.5 equiv) dropwise at 0 C and the reaction was stirred at rt overnight. To the reaction was added 600 mL of water and the reaction was stirred for 30 min. All insoluble was removed by filtration and the solid was triturated with ethyl acetate (EA, 3 ¡Á 100 mL) for 40 min and filtered. The filtrate was washed with saturated sodium carbonate (3 ¡Á 200 mL), saturated sodium chloride (200 mL) and dried over anhydrous sodium sulfate.The solvent was removed under reduced pressure to give 22 as a solid (42 g, yield 87.3%). To a solution of 22 (20 g, 102.2 mmol, 1 equiv) in CCl4 (200 mL) was added NBS (18.2 g, 102.0 mmol, 1.0 equiv), Bz2O2 (0.15 g, 0.6 mmol, 0.006 equiv). The reaction was refluxed overnight under N2, cooled and filtered. The filtrate was crystallized at 0 C to provide the brominated intermediate (15 g, yield 53.6%). To a solution of the brominated intermediate (90 g, 327.3 mmol) in DMF (760 ml) was added KOAc (38.6 g, 393.1 mmol, 1.2 equiv). The reaction mixture was stirred at 80 C for 1 h, cooled and water (1 L) was added. The mixture was extracted with EA (1 L). The organic layer was washed with 0.5 N HCl (3 ¡Á200 mL), 2% NaHCO3 (200 mL) and dried over anhydrous sodium sulfate. The solvent was removed to give 23 as a yellow solid (77.3 g, yield 92.9%). 1H NMR of 23 (500 MHz, CDCl3): delta 2.16 (s, 3H), 5.21 (s, 2H), 7.43-7.46 (t, 1H,), 7.63 (m, 2H) ppm. To a solution of 23 (20 g, 78.8 mmol) in 1,4-dioxane (400 mL) was added bis(pinacolato)diboron (30 g, 118.1 mmol, 1.5 equiv) and KOAc (33.2 g, 338.1 mmol, 4.3 equiv). After being de-gassed and backfilled with nitrogen, Pd(dppf)Cl2 (3.2 g, 3.935 mmol, 0.05 equiv) was added. The reaction was refluxed overnight under nitrogen, cooled and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography eluted with petroleum ether (PE)/EA = 5:1 to give 24 as red oil (29 g, crude yield 100% with 80% purity). 1H NMR of 24 (500 MHz, DMSO-d6): delta 1.42 (s, 12H), 2.20 (s, 3H), 5.25 (s, 2H), 7.44-7.49 (t, 1H), 7.57-7.64 (m, 2H) ppm. To a solution of 24 (29 g) in MeOH (100 mL) was added a solution of NaOH in MeOH (7.0 g/130 mL, 175.8 mmol, 2.3 equiv) and the reaction was stirred for 2 h at rt. The reaction mixture was concentrated under vacuum and the residue was dissolved in THF (150 mL) and 2 N HCl (138 mL, 69 mmol, 0.9 equiv). The reaction was stirred at rt for 50 min, concentrated and filtered. The solid was washed with water (3 ¡Á 20 mL) and petroleum ether (3 ¡Á 20 mL) to provide 25 (7.6 g, yield 62%). 1H NMR of 25 (500 MHz, DMSO-d6): delta 5.05 (s, 2H), 7.63-7.68 (t, 1H), 7.73-7.81 (m, 2H) ppm. To Raney Ni (0.849 g, 14.5 mmol, 2.3 equiv) in formic acid (10 mL) and water (2 mL) was added 25 (1 g, 6.29 mmol) at rt. The reaction was stirred at 100 C for 1 h, cooled and then filtered. The solvent was removed to give a solid that was purified by silica gel column chromatography eluted with CH2Cl2 to give 26 as a solid (0.714 g, yield 70%). 1H NMR of 26 (500 MHz, CDCl3): delta 10.03 (s, 1H), 8.08 (s, 1H), 7.86 (t, 1H), 7.63-7.71 (m, 2H), 5.20 (s, 2H) ppm. To a mixture of HCOOH (116.2 g, 10.0 equiv) and TEA (102.2 g, 4.0 equiv) were added 26 (40.9 g, 252.5 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (43.7 g, 1.2 equiv). The resulting mixture was refluxed for 15 h and cooled to rt. Hydrochloric acid (2 N, 320 mL) was added into the mixture that was then extracted with ethyl acetate twice (2 ¡Á 250 mL). The combined organic layer was washed with 2 N HCl (160 mL) and rotary evaporated to give the crude product that was recrystallized from DMF and 2 N HCl (34:204 mL) providing compound 1 as a white solid (15.6 g, yield 30%). An additional recrystallization from DMF and 2 N HCl (16:96 mL) was performed to give high purity product (12.9 g).

The chemical industry reduces the impact on the environment during synthesis 42872-74-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Yong-Kang; Plattner, Jacob J.; Freund, Yvonne R.; Easom, Eric E.; Zhou, Yasheen; Gut, Jiri; Rosenthal, Philip J.; Waterson, David; Gamo, Francisco-Javier; Angulo-Barturen, Inigo; Ge, Min; Li, Zhiya; Li, Lingchao; Jian, Yong; Cui, Han; Wang, Hailong; Yang, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 2; (2011); p. 644 – 651;,
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103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Experiment 37: Experiment 11 was repeated except that a mixture of 1-propanol and ethanol (50:50) was used as the solvent in stead of 1-propanol in a total volume of 4.4 V, 0.5 eq of (+)-O,O’-di-/?-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was 0.5 h. Molar yield: 27.4%, enantiomeric purity: 99.4% S.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
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622-75-3, 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. 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, A new synthetic method of this compound is introduced below.

Add 4- (2-oxiranylmethoxy) benzaldehyde (0.01 mol, 1.78 g), terephthalonitrile (0.0045 mol, 0.7000 g), and 150 mL of ethanol to a 250-mL single-necked bottle, and stir for 10 minutes. After several minutes, solid potassium hydroxide (0.03 mol, 1.68 g) was added, and after 4 to 6 hours of reaction, the reaction was stopped.After the temperature of the reaction system was cooled to room temperature, the solid product was collected by suction filtration, washed with water and dried to obtain a crude product. The crude product was recrystallized from a mixed solvent of DMF and ethanol (V: V = 3: 1) to obtain a pure yellow product 1.95. g, yield 93%.

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; Xiangtan University; Zhang Hailiang; Tan Huiping; Yuan Yongjie; Yang Bohao; (15 pag.)CN110407772; (2019); A;,
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These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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. 60702-69-4

To a solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 7 33 (7.00 g, 60.8 mmol) in THF (120 mL) was added sodium bis(2-methoxyethoxy)aluminium dihydride (70% in toluene, 59.7 mL, 215 mmol) slowly at 5 C. After stirring at 70 C for 3 h, the reaction mixture was cooled to 5 C followed by addition of sodium carbonate decahydrate (26.1 g, 91.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with THF, and the precipitate was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in DMSO (80 mL). To the solution was added lithium carbonate (8.99 g, 122 mmol) and 2-chloro-4-fluorobenzonitrile (9.46 g, 60.9 mmol), and the mixture was stirred at 100 C for 1 h. The mixture was diluted with EtOAc and H2O, and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (10.7 g, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3) delta: 1.18 (3H, d, J = 6.6 Hz), 1.82 (1H, d, J = 5.5 Hz), 2.01-2.14 (1H, m), 2.25-2.35 (1H, m), 3.19-3.28 (1H, m), 3.43-3.51 (1H, m), 3.89-3.98 (1H, m), 4.43-4.52 (1H, m), 6.43 (1H, dd, J = 8.9 and 2.4 Hz), 6.56 (1H, d, J = 2.4 Hz), 7.42 (1H, d, J = 8.9 Hz). MS (ESI) m/z 237 [(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 60702-69-4.

Reference:
Article; Yamamoto, Satoshi; Kobayashi, Hiromi; Kaku, Tomohiro; Aikawa, Katsuji; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 70 – 83;,
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These common heterocyclic compound, 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, 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. 332-25-2

The 4 – trifluoro nitrile (187 mg, 1mmol), butyric aldehyde wo (96 mg, 1 . 1mmol), [Cp * IrCl2]2(8 mg, 0 . 01mmol, 1 muM percent), toluene (1 ml) are added to the 25 ml Schlenk reaction bottle. The mixture 100 ¡ãC reaction under 6 hours, cooling to room temperature. The benzyl alcohol (140 mg, 1 . 3mmol) and cesium carbonate (65 mg, 0.2 equiv.) is added to the bottle in the reaction, the mixture 130 ¡ãC then continue to react under 12 hours, cooling to room temperature. The solvent is removed by rotary evaporation, then through the column chromatography (developing solvent: ethyl acetate/petroleum ether) to obtain the pure target compound, yield: 82percent.

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 332-25-2.

Reference:
Patent; Nanjing University of Science and Technology; Li Feng; Wang Nana; Zou Xiaoyuan; (15 pag.)CN105016938; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 23842-82-2, name is 2-Amino-5-methoxybenzonitrile, 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 23842-82-2, 23842-82-2

Ketone (¡À)-5 (95 mg, 0.63 mmol) was dissolved in dry 1,2-dichloroethane (1 mL). AnhydrousAlCl3 (126.5 mg, 0.95 mmol) and 7 (121 mg, 0.79 mmol) were added to this solution. The mixturewas stirred under MW (50W, 300 psi, high stirring) conditions at 95 C for 2 h. After the completionof the condensation, mixture of THF/H2O (7.5 mL, 2:1) was added, followed by 2 M aq. solution ofNaOH adjusting pH to 8-9. The resulting mixture was stirred for 30 min. The organic and aqueousphases were separated and the aqueous one was washed with dichloromethane (2 8 mL). Combinedorganic layers were dried over anhydrous Na2SO4 and the solvent was removed under reducedpressure. The crude product was purified by column chromatography (CH2Cl2/MeOH/TEA, 95:5:1).Compound (¡À)-1 (142 mg) was obtained in 80% yield in two steps as 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-Amino-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mezeiova, Eva; Korabecny, Jan; Sepsova, Vendula; Hrabinova, Martina; Jost, Petr; Muckova, Lubica; Kucera, Tomas; Dolezal, Rafael; Misik, Jan; Spilovska, Katarina; Pham, Ngoc Lam; Pokrievkova, Lucia; Roh, Jaroslav; Jun, Daniel; Soukup, Ondrej; Kaping, Daniel; Kuca, Kamil; Molecules; vol. 22; 8; (2017);,
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658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below.

Under protective gas (argon), 125 mg (1.11 mmol) of potassium tert-butoxide were added to 1.006 g (5.55 mmol) of methyl (2E)-3-(5-fluoropyridin-3-yl)acrylate and 0.850 g (5.55 mmol) of (3,4-difluorophenyl)acetonitrile in 45.0 ml of toluene and 2 ml of DMF, and the mixture was stirred at 60 C. for 5 h. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 1.050 g (57% of theory) of the diastereomeric methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoates.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; MOSRIN, MARC; JAKOBI, HARALD; DIETRICH, HANSJOERG; GATZWEILER, ELMAR; ROSINGER, CHRISTOPHER HUGH; SCHMUTZLER, DIRK; (66 pag.)US2017/290330; (2017); A1;,
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3939-09-1, Name is 2,4-Difluorobenzonitrile, 3939-09-1, 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.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile. To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in THF (20 mL), and DMF (40 mL) was added 1,2,4-triazole sodium (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% EtOAc/hexanes to give the 4-triazolyl isomer as colorless needles (2.46 g, 18%) and the 2-substituted isomer as a white solid (0.7455 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile. 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13.

Statistics shows that 2,4-Difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 3939-09-1.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3939-09-1, name is 2,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3939-09-1

4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture was stirred at 22 C. for 18 h. The solid was then filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The mixture containing the 2 and 4-triazolyl-benzonitriles was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and on reversed phase silica gel to give 1.86 g (18% yield) of 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 0.526 g (5% yield) of 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate/hexanes). mp 117-118 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.54 (3H, s, CH3), 7.24 (1H, m, CH), 7.62 (1H, dd, J=2.5 Hz and J=9.1 Hz, CH), 7.84 (1H, dd, J=5.6 Hz and J=8.6 Hz, CH), 8.82 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. Found: C, 59.25; H, 3.32; N, 27.81. 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane). mp 120-121 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.56 (3H, s, CH3), 7.30 (1H, dd, J=2.5 Hz and J=8.1 Hz, CH), 7.39 (1H, m, CH), 7.91 (1H, dd, J=5.5 Hz and J=8.6 Hz, CH), 8.06 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. Found: C, 59.35; H, 3.70; N, 27.77.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts