Diisopropylethylamine → HCID 89783751, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (40 mg, 0.13 mmol), 2-methyl-1-morpholinopropan-2-amine dihydrochloride [prepared according to the procedures reported in US 20060035903 A1 (2006)] (62 mg, 0.27 mmol) and DIPEA (0.14 mL, 0.81 mmol) in DMSO (2 mL) in a sealed glass tube was heated at 160° C. in a microwave for 45 min. It was diluted with 50 mL of EtOAc, washed with 5 mL of sat. NaHCO3 followed by 5 mL of brine. The organic solution was concentrated and the residue was purified on a silica gel column (3% MeOH in DCM followed by 3-10% of 2 M NH3 in MeOH in DCM) to provide the title compound (17 mg, 29% yield) as a yellow off white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.85 (1H, br.), 7.79 (1H, dd, J=7.4, 1.2 Hz), 7.60 (1H, dd, J=8.0, 1.2 Hz), 7.35 (1H, t, J=7.7 Hz), 7.02 (1H, s), 6.96 (1H, s), 6.32 (1H, s), 3.60 (4H, m), 3.44 (2H, td, J=6.9, 2.2 Hz), 3.30 (4H, m), 2.86 (2H, t, J=6.8 Hz), 2.70 (2H, s), 2.58 (3H, s), 1.55 (6H, s). m/z (ESI, +ve) 435.0 (M+H)+.

Provenance & Evidence