1,2-Dichloroethane → HCID 136337160, compound

Participants

Reaction Conditions

Reaction Steps

Titanium (IV) chloride (0.25 mL, 2.3 mmol) was added to a solution of 1-{[4-(2,6-dimethyl-phenoxy)-3-methyl-phenylamino]-ethoxycarbonylimino-methyl}-1H-pyrazole-4-carboxylic acid ethyl ester (0.97 g, 2.1 mmol) and DCE (10 mL), and the resulting mixture was heated to 90° C. for 16 h. The reaction mixture was cooled to room temperature and poured into 50 mL EtOH. The mixture was stirred for 30 min and concentrated to dryness. The solid was and purified by FCC (CH3CN/DCM, gradient 0:100 to 20:80) to provide the titled compound (0.28 g, 32%). MS (ESI): mass calcd. for C23H22N4O4, 418.4; m/z found, 419.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.77 (s, 1H), 8.96 (s, 1H), 8.28 (s, 1H), 7.69 (s, 1H), 7.25 (d, J=7.4 Hz, 2H), 7.18 (dd, J=8.3, 6.7 Hz, 1H), 6.78 (s, 1H), 4.30 (q, J=7.1 Hz, 2H), 2.55 (s, 3H), 2.08 (s, 6H), 1.32 (t, J=7.1 Hz, 3H).

Provenance & Evidence