1,2-Dichloroethane → HCID 68412346, compound

Participants

Reaction Conditions

Reaction Steps

EDC (0.21 g, 1.1 mmol) was added to a suspension of methyl-(2-methyl-benzofuran-3-ylmethyl)-amine (158 mg, 0.9 mmol) and 3-(4-Methyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid hydrochloride (201 mg, 0.75 mmol). The mixture was allowed to stir overnight at 40° C. The mixture was cooled to 0° C. and diluted with H2O (60 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (20 mL) then dried under high vacuum. The solid was then subjected to flash chromatography on silica gel using 5% methonal:dichloromethane. The fractions were collected and treated with 5 mL of 2.0M HCL in Et2O. The suspension was concentrated, triturated with Et2O (50 Ml then filtered to give a coupled solid. The resulting solid was dissolved in methylene chloride (5 mL) and treated with 2M HCl in ether (0.75 mL, 1.5 mmol). The resultant yellow precipitate was filtered, triturated with diethyl ether and dried under high vacuum to afford the title compound as a white solid (186 mg, 53%) and a mixture of amide rotomers. 1H NMR (300 MHz, DMSO-d6) 11.80 (bs, 1H) 8.45-8.17 (m, 2H), 7.56-7.46 (m, 3H), 7.29-7.14 (m, 3H), 4.82-4.97 (m, 2H), 4.60-4.70 (m, 1H), 4.30-4.40 (m, 1H), 3.65-3.75 (m, 3H), 3.33-3.45 (m, 1H), 2.89-2.78 (m, 2H) 2.82 (s, 3H), 2.25 (s, 3H); MS (ESI) m/e 391 (C23H26N4O2+H)+.

Provenance & Evidence