Category: 591769-05-0

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 591769-05-0 as follows. Computed Properties of C8H11N

Racemic 3-cyclopentyl-3-{4-[7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl}propionitrile (9, racemic SEM-protected compound).; Method A.; 3-Cyclopentylacrylonitrile (8, 273.5 g, 2.257 mol, 1.20 equiv) and DBU (28 mL, 0.187 mol, 0.10 equiv) was added to a suspension of 4-(1H-pyrazol-4-yl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (5, 591.8 g, 1.876 mol) in acetonitrile (4.7 L) at room temperature. The resulting reaction mixture was heated to 50-60¡ã C. for 17 hours (a clear solution developed midway through heating) then to 70-80¡ã C. for 8 hours. When LCMS analysis showed the reaction was deemed complete, the reaction mixture was cooled to room temperature. The cooled solution was then concentrated under reduced pressure to give the crude product (9) as a thick amber oil. The crude product was dissolved in dichloromethane (DCM) and absorbed onto silica gel then dry-loaded onto a silica column (3 Kg) packed in 33percent EtOAc/heptanes. The column was eluted with 33percent EtOAc/heptanes (21 L), 50percent EtOAc/heptanes (28 L), 60percent EtOAc/heptanes (12 L) and 75percent EtOAc/heptanes (8 L). The fractions containing the desired product (9) were combined and concentrated under reduced pressure to generate a yellow oil, which was transferred to a 3 L flask with EtOAc. The solvent was removed under reduced pressure and the residual EtOAc by co-evaporating with heptanes. The residue was further dried under high vacuum for overnight to afford racemic 3-cyclopentyl-3-{4-[7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl}propionitrile (9, racemic SEM-protected compound, 800 g, 819.1 g theoretical, 97.7percent yield) as an extremely viscous yellow oil. For 9: 1H NMR (DMSO-d6, 400 MHz) delta ppm 8.83 (s, 1H), 8.75 (s, 1H), 8.39 (s, 1H), 7.77 (d, 1H, J=3.7 Hz), 7.09 (d, 1H, J=3.7 Hz), 5.63 (s, 2H), 4.53 (td, 1H, J=19.4, 4.0 Hz), 3.51 (t, 2H, J=8.1 Hz), 3.23 (dq, 2H, J=9.3, 4.3 Hz), 2.41 (m, 1H), 1.79 (m, 1H), 1.66-1.13 (m, 7H), 0.81 (t, 2H, J=8.2 Hz), 0.124 (s, 9H); C23H32N6OSi (MW, 436.63), LCMS (EI) m/e 437 (M++H) and 459 (M++Na).

According to the analysis of related databases, 591769-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
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Synthetic Route of 591769-05-0, The chemical industry reduces the impact on the environment during synthesis 591769-05-0, name is 3-Cyclopentylacrylonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 4-[3-(fluoromethyl)-1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl) ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (1.0 eq.) and 3-cyclopentylacrylonitrile (2.5 eq., prepared from the step A of Example 1) in acetonitrile was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.0 eq.) at room temperature. The reaction liquid was stirred for 5 hrs at room temperature, then warmed to 60¡ãC and stirred overnight. After the reaction liquid was cooled to room temperature, the reaction liquid was diluted with brine and ethyl acetate, and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was separated by column chromatography on silica gel column to give the titled compound. m/z=469[M+1]+.

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

Reference:
Patent; Centaurus BioPharma Co., Ltd.; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Lianyungang Runzhong Pharmaceutical Co., Ltd.; ZHU, Li; XIAO, Dengming; HU, Yuandong; DAI, Liguang; DUAN, Xiaowei; SUN, Yinghui; PENG, Yong; KONG, Fansheng; LUO, Hong; HAN, Yongxin; YANG, Ling; WANG, Shanchun; (94 pag.)EP3235819; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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 591769-05-0, 591769-05-0

3.0g of compound 9 and 2.9g of compound 5a were dissolved in 150mL acetonitrile. To the above solution, 0.10g of 1,8-diazabicyclo undec-7-ene was added and reacted at 65¡ãC for 2 days. TLC was used to determine reaction completion. After distilling off the solvent, it was dissolved in ethyl acetate then water and aqueous citric acid solution was added. 100mL saturated sodium chloride solution was washed 3 times each. The organic phase was dried over anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by column chromatography (methylene chloride/methanol 80:1) to give 2.4g of intermediate 10a as a white solid, yield: 48percent.

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

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 591769-05-0 as follows. 591769-05-0

To a solution of 4-iodo-lH-pyrazole 34e (0.72 g, 3.75 mmol) in acetonitrile (10 mL) was added 3-cyclopentylacrylonitrile 34c (0.5 g, 4.12 mmol) and DBU (0.57 g, 3.75 mmol). The reaction mixture was stirred at room temperature and concentrated in vacuum. The residue obtained was dissolved in ethyl acetate washed with 1 N aqueous HC1, brine, dried and concentrated in vacuum to furnish crude as oil. The crude was purified by flash column chromatography (silica gel 24 g, eluting with 0-50percent ethyl acetate in hexane) to furnish 3- cyclopentyl-3-(4-iodo-lH-pyrazol-l-yl)propanenitrile 34f (0.845 g, 72percent) as a colorless oil;1HNMR (300 MHz, DMSO) delta 8.06 (d, J= 0.6, 1H), 7.61 (s, 1H), 4.40 (td, J= 5.2, 9.0, 1H), 3.20 – 3.04 (m, 2H), 2.39 – 2.21 (m, 1H), 1.74 (m, 1H), 1.63 – 1.36 (m, 4H), 1.33 – 1.18 (m, 2H), 1.13 – 1.02 (m, 1H).

According to the analysis of related databases, 591769-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KOTIAN, Pravin L.; KUMAR, V. Satish; WU, Minwan; LIN, Tsu-Hsing; WO2011/31554; (2011); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 591769-05-0, name is 3-Cyclopentylacrylonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 591769-05-0

To a solution of -4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (15.0 g,0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cis and trans isomers),followed by DBU (15 mL, 0.10 mol). The resulting mixture was stirred at room temperature overnight. The ACN wasevaporated. The mixture was diluted with ethyl acetate, and the solution was washed with 1.0 N HCl. The aqueous layerwas back-extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, driedover sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradientof ethyl acetate/hexanes) to yield a viscous clear syrup, which was dissolved in ethanol and evaporated several timesto remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H, 15percent ethanol/hexanes) and used separately in the next step to generate their corresponding final product.The final products (see Step 3) stemming from each of the separated enantiomers were found to be active JAK inhibitors;however, the final product stemming from the second peak to elute from the preparative-HPLC was more active thanits enantiomer.1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H), 8.32 (s, 2H), 7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H),3.54 (t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H), 2.03-1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H), -0.06(s, 9H); MS(ES):437 (M+1).

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, 591769-05-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Holdings Corporation; PARIKH, Bhavnish; SHAH, Bhavesh; YELESWARAM, Krishnaswamy; (55 pag.)EP2574168; (2016); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts