Acetone → HCID 66605060, compound

Participants

Reaction Steps

A suspension of 7-amino-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (30 mg, 0.081 mmol), propan-2-one (0.118 mL, 1.62 mmol), and sodium triacetoxyborohydride (172 mg, 0.810 mmol) in a mixture of DCM/THF (2/1) (3 mL) was stirred at RT overnight. The mixture was diluted with MeOH and preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 7-(isopropylamino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (20 mg, 0.045 mmol, 55% yield). MS (ESI) m/z 413.20 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.13 (1H, s), 8.58 (2H, s), 8.51 (1H, s), 8.29 (1H, s), 7.90 (1H, d J=8.56 Hz), 7.81 (1H, s), 7.68-7.77 (2H, m), 6.80 (1H, d, J=1.76 Hz), 6.60 (1H, dd, J=8.56, 2.01 Hz), 6.00 (1H, d, J=7.55 Hz), 3.53-3.68 (1H, m), 1.21 (6H, d, J=6.30 Hz).

Provenance & Evidence