Nitrogen mustard hydrochloride → HCID 178433636, compound

Participants

Reaction Steps

A stirred mixture of 7-(3-aminophenyl)-2-(4-chlorophenyl)-2,5-dihydro-6-methylpyrazolo[4,3-c]pyridin-3-one (0.1997 g, 0.570 mmol), and mechlorethamine hydrochloride (0.1293 g, 0.672 mmol) in anhydrous 1-butanol (4 ml) was heated at reflux under nitrogen for 50 h, adding sodium carbonate (24.7 mg, 0.233 mmol) after 22 h and more mechlorethamine hydrochloride (0.4807 g, 2.50 mmol) after 26 h. The solvent was removed in vacuo and the residue was purified by flash chromatography [silica gel, 5-30% MeOH/CH2Cl2; then silica gel, CH2Cl2-MeOH-NH3 (95:5:0.5 to 93:7:0.7)], to afford 29.6 mg (12%) of the title compound as a yellow solid; mp 191-210° C. (CH2Cl2-EtOAc-hexane); 1H NMR (360 MHz, DMSO-d6) δ2.25 (3H, s), 2.26 (3H, s), 2.50 (4H, m), 3.20 (4H, m), 6.89 (1H, d, J 7.5 Hz), 6.99 (1H, m), 7.05 (1H, s), 7.33 (1H, t, J 7.9 Hz), 7.42 (2H, d, J9.0 Hz), 8.13 (2H, d, J8.9 Hz), 8.54 (1H, s), 12.44 (1H, br s); MS (ES+) m/z 434/436[MH]+, 218[(M+2H)/]+. Anal. found: C, 64.41; H, 5.63; N, 15.44. C24H24ClN5O.0.7H2O requires: C, 64.56; H, 5.73; N, 15.68%.

Provenance & Evidence