15205-15-9, These common heterocyclic compound, 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, 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.
Step 1: (S) -tert-Butyl (1- (4- ( (2-chloro-6-fluorobenzyl) carbamoyl) -2- (3-ethoxy-4-methoxyphenyl) oxazol-5-yl) ethyl) carbamate[0639]To 10 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3-ethoxy-4-methoxyphenyl) oxazole-4-carboxylic acid (0.3 g, 0.74 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (212 mg, 1.11 mmol) and 1-hydroxy-7-azabenzotriazole (151 mg, 1.11 mmol) , and the mixture was stirred at 0 for 30 minutes. To the mixture were added dropwise (2-fluoro-6-chlorophenyl) methanamine (0.11 mL, 0.89 mmol) and N, N-diisopropylethylamine (0.39 mL, 2.21 mmol) in turn, and the resulting mixture was stirred at rt for 12 hours. The reaction mixture was washed with water (10 mL ¡Á 3) , and the organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 6/1) to give the title compound as a white solid (190 mg, 47) .[0640]1H NMR (400 MHz, CDCl3) : delta ppm 7.60 (dd, J1 8.4 Hz, J2 1.9 Hz, 1H) , 7.52 (d, J 1.8 Hz, 1H) , 7.39 -7.29 (m, 1H ) , 7.27 -7.25 (m, 1H) , 7.10 -7.05 (m, 1H) , 6.94 (d, J 8.5 Hz, 1H) , 5.30 -5.25 (m, 1H) , 4.91 -4.84 (m, 2H) , 4.23 -4.18 (m, 2H) , 3.95 (s, 1H) , 1.57 -1.51 (m, 6H) , 1.45 (s, 9H) and MS-ESI: m/z 549.2 [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 15205-15-9.
Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
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