Category: 3047-38-9

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. 3047-38-9, name is Cyclopent-1-enecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H7N

To a stirred solution of cyclopent- l-enecarbonitrile (50 g, 537 mmol) in carbon tetrachloride (400 ml) at 25C was added N-bromosuccinimide (96 g, 537 mmol) under nitrogen atmosphere. The resulting mixture was refluxed for 2 h. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25C and filtered through Celite. The filtrate was concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel ( 100 – 200 mesh) using 1% ethyl acetate in hexane as an eluent to obtain the title compound (60 g, 65%). iHNMR (CDCls, 400MHz): delta 6.77-6.73 (m, IH), 5. 12-5.09 (m, IH) 2.95-2.86 (m, lH) 2.67-2.42 (m, 3H).

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 3047-38-9.

Reference:
Patent; LUPIN LIMITED; JANA, Gourhari; SINHA, Neelima; KARCHE, Navnath, Popat; KURHADE, Sanjay, Pralhad; TILEKAR, Ajay, Ramchandra; GUPTA, Nishant, Ramniwasji; IRLAPATI, Nageswara, Rao; KUKREJA, Gagan; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (102 pag.)WO2016/12956; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3047-38-9, name is Cyclopent-1-enecarbonitrile, 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. name: Cyclopent-1-enecarbonitrile

Into a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-3-amine (1-1; 250 g, 1.04 mol), ethanol (3000 mL), cyclopent-l-ene-l-carbonitrile (300 g, 3.22 mol), and DBU (317 g, 2.08 mol). The resulting solution was heated to reflux and stirred overnight. The reaction mixture was cooled and concentrated in vacuo, and the resulting residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10-1 :2) to afford racemic-2-[3- amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 -yljcyclopentane- 1 -carbonitrile. The racemic 2-[3-amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 – yljcyclopentane- 1 -carbonitrile (100 g, 300 mmol) was purified using Chiral Prep-SFC with the following conditions: Column Used: Phenomenex Lux Cellulose-4, 2 x 25cm, 5 muiotaeta Mobile phase: C02 (80%), methanol with 0.1% DEA (20%) Wavelength: UV 254 nm. Peak A, 1-6: (lR,2R)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane- 1 -carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H). Peak B, 1-7: (llS’,2lS,)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane-l- carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H).

The synthetic route of 3047-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 3047-38-9, 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. 3047-38-9 name is Cyclopent-1-enecarbonitrile, 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.

Step 1: 3-bromocyclopent-1-enecarbonitrile To a stirred solution of cyclopent-1-enecarbonitrile (50 g, 537 mmol) in tetrachloromethane (400 ml) at 25 C. was added was added N-bromosuccinimide (96 g, 537 mmol) under nitrogen atmosphere. The resulting mixture was refluxed for 2 h. The progress of reaction was monitored by TLC. The reaction mixture cooled to 25 C. and filtered through celite. The filtrate was concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 1% ethyl acetate in hexane as an eluent to obtain the title compound (60 g, 65%). 1HNMR (CDCl3, 400 MHz): delta 6.77-6.73 (m, H), 5.12-5.09 (m, 1H) 2.95-2.86 (m, 1H) 2.67-2.42 (m, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Cyclopent-1-enecarbonitrile, and friends who are interested can also refer to it.