Ammonia → HCID 66605104, compound

Participants

Reaction Steps

A suspension of 7-(isopropylamino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (13 mg, 0.032 mmol), formaldehyde (0.023 mL, 0.315 mmol, 37% aq. solution), and sodium triacetoxyborohydride (33 mg, 0.16 mmol) in a mixture of DCM/THF (2/1) (0.3 mL) was stirred at RT overnight. The crude reaction 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-(isopropyl(methyl)amino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (6 mg, 0.011 mmol, 38% yield). MS (ESI) m/z 427.13 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.17 (1H, br. s.), 8.60 (2H, d, J=1.53 Hz), 8.54 (1H, br. s.), 8.35 (1H, s), 8.03 (1H, d, J=8.85 Hz), 7.83 (1H, br. s), 7.73-7.78 (2H, m), 7.07 (1H, d, J=2.14 Hz), 6.87 (1H, dd, J=8.85, 2.14 Hz), 4.24 (septupled, 1H, J=6.6), 2.82 (3H, s), 1.21 (6H, d, J=6.41 Hz).

Provenance & Evidence