Cyclopropylamine → HCID 89783610, compound

Participants

Reaction Steps

A solution of ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (325b) (218 mg, 0.480 mmol), cyclopropanamine (82 mg, 1.44 mmol) and DIEA (0.17 mL, 0.96 mmol) in 3 mL of DMSO was heated in an oil bath at 80° C. for 5 h. It was diluted with 50 mL of EtOAc, washed with 5 mL of water. The organic solution was concentrated and the residue was stirred in 5 mL of ether. The insoluble yellow solid was filtered, rinsed with 2×2 mL of ether to give 133 mg of ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate, as a yellow crystalline solid. The filtrate was concentrated and the residue was purified on a silica gel column (25-70% EtOAc in Hexanes) to give 67 mg ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.31 (1H, br.), 8.05 (1H, m), 7.61 (1H, dd, J=8.0, 1.2 Hz), 7.42 (1H, d, J=3.5 Hz), 7.35 (1H, t, J=7.8 Hz), 7.26 (1H, br.), 7.02 (2H, br.), 4.28 (2H, q, J=7.0 Hz), 2.56 (3H, s), 1.35 (4H, m), 1.32 (9H, s), 1.03-1.19 (5H, m), 0.63-0.78 (2H, m). m/z (ESI, +ve) 492.2 (M+H)+.

Provenance & Evidence