Triethylamine → (S)-7-(3-(dimethylamino)pyrrolidine-1-carbonyl)-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide

Participants

Reaction Steps

Dimethylformamide (5 mL) was added to a mixture of 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acid (70 mg, 0.19 mmol), (3S)-(+3-(dimethylamino)pyrrolidine (0.070 mL, 0.55 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (106 mg, 0.554 mmol), and 1-hydroxybenzotriazole hydrate (75 mg, 0.55 mmol). After stirring for a few minutes, triethylamine (0.077 mL, 0.55 mmol) was added and the reaction was left stirring overnight. It was diluted with EtOAc, washed with water, dried with sodium sulfate and the solvent was removed. The residue was suspended in DCM at 40° C. for 10 min and then filtered to gave (S)-7-(3-(dimethylamino)pyrrolidine-1-carbonyl)-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (40 mg) as a yellow solid. MS (ESI) m/z 476.2 (M+H). 1H NMR (DMSO-d6) δ ppm 11.71 (1H, br. s.), 8.62 (1H, br. s.), 8.47 (1H, s), 8.30 (1H, dd, J=7.48, 4.43 Hz), 8.09-8.21 (2H, m), 7.92 (2H, m), 7.42 (1H, m), 7.36 (1H, m), 3.95 (3H, s), 3.64-3.82 (1H, m), 3.47-3.63 (2H, m), 3.36 (1H, m), 2.61-2.83 (1H, m), 2.22 (3H, s), 2.11 (3H, s), 2.03 (1 H, br. s.), 1.68-1.85 (1H, m).

Provenance & Evidence