Diisopropylethylamine → HCID 66604256, compound

Participants

Reaction Steps

A mixture of 1,4-oxazepane (15 mg, 0.15 mmol), 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylic acid (50 mg, 0.15 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.071 mL, 0.41 mmol) in dry DMF (1.3 mL) was stirring for a few minutes and then benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (80 mg, 0.18 mmol) was added. After 1 hr, the reaction was diluted with MeOH and preparative HPLC (PHENOMENEX® Luna 30×100 mm C18, Solvent A=10% acetonitrile -90% H2O—0.1% TFA; Solvent B=90% acetonitrile—10% H2O —0.1% TFA, 10-70% B gradient over 18 min) afforded 7-(1,4-oxazepane-4-carbonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (45 mg, 0.11 mmol, 70% yield) as a yellow solid. MS (ESI) m/z 415.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.75 (1H, br. s.), 8.65 (1H, br. s.), 8.50 (1H, s), 8.31 (3H, d, J=7.63 Hz), 7.92 (1H, br. s.), 7.78 (1H, br. s.), 7.56 (2H, t, J=7.63 Hz), 7.45 (1H, t, J=7.32 Hz), 7.28 (1H, d, J=7.63 Hz), 3.77 (5H, br. s.), 3.65 (1H, br. s.), 3.50 (2H, br. s.), 1.94 (1H, br. s.), 1.79 (1H, br. s.).

Provenance & Evidence