Water → HCID 66605059, compound

Participants

Reaction Steps

A mixture of 7-amino-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (70 mg, 0.189 mmol), N-benzyl-2-chloro-N-(2-chloroethyl)ethanamine hydrochloride (102 mg, 0.378 mmol) and Na2CO3 (100 mg, 0.945 mmol) in t-BuOH (2 mL) was heated at reflux overnight. 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) and SCX capture and release with 2 N NH3 in MeOH afforded 7-(4-benzylpiperazin-1-yl)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (50 mg, 0.090 mmol, 48% yield). MS (ESI) m/z 530.29 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.33 (1H, s), 8.54-8.64 (3H, m), 8.41 (1H, s), 8.07 (1H, d, J=8.85 Hz), 7.88 (1H, br. s.), 7.72-7.80 (2H, m), 7.35-7.41 (4H, m), 7.26-7.32 (1H, m), 7.22 (1H, d, J=1.83 Hz), 7.01 (1H, dd, J=8.85, 1.83 Hz), 3.57 (2H, s), 3.30 (4H, d, J=3.97 Hz), 2.59 (4H, d, J=3.97 Hz).

Provenance & Evidence