Some common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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. Computed Properties of C4H7ClN2
A mixture of 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylic acid, (EXAMPLE 149), (0.070 g, 0.188 mmol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.147 g, 0.282 mmol), diisopropylethylamine (0.049 ml, 0.282 mmol), and 1-amino-1-cyclopropanecarbonitrile hydrochloride (0.033 g, 0.282 mmol) in DCM (5 mL) was stirred at room temperature for 12 hours. Purification of the reaction mixture using silica chromatography with ISCO eluting with 0-80% EtOAc/hexanes gave the title compound N-(1-cyanocyclopropyl)-2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxamide (0.060 g, 0.137 mmol, 73.1% yield). m/z: 437 (M+1); 1H NMR (400 MHz, DMSO-d6) delta: ppm 8.78 (s, 1H) 8.32 (d, J=6.65 Hz, 1H) 7.93-8.05 (m, 2H) 7.40 (s, 1H) 5.18 (quin, J=8.51 Hz, 1H) 4.31-4.53 (m, 1H) 3.21-3.41 (m, 2H) 2.88-3.05 (m, 1H) 2.29-2.44 (m, 2H) 1.44-1.60 (m, 2H) 1.23-1.35 (m, 2H) 0.93-1.10 (m, 4H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127946-77-4, its application will become more common.
Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts