Dimethylformamide → (4Z)-N,N-dimethyl-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-1,3-dioxoisoquinoline-6-carboxamide

Participants

Reaction Steps

Prepared from a slurry of 81.7 mg (0.298 mmol) of 4-methoxymethylene-1,3-dioxo-1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid dimethylamide and 56.9 mg (0.298 mmol) of 4-(4-methylpiperazin-1-yl)methyl-phenylamine in 1.5 mL of N,N-dimethylformamide (DMF) at 100° C. under N2 as described for example 21. After heating for 0.5 h, the reaction is chilled in ice. The solid product is collected, washed with N,N-dimethylformamide (DMF) and Et2O and dried to give 111 mg (86%) of yellow crystals: mp >300° C.; 1H NMR (DMSO-d6) δ 12.55 (d, 1H, J=12.8 Hz), 11.25 (s, 1H), 8.88 (d, 1H, J=12.8 Hz), 8.14 (s, 1H), 8.03 (d, 1H, J=8.07 Hz), 7.46 (d, 2H, J=8.94), 7.16 (d, 1H, J=8.07 Hz), 6.98 (d, 2H, J=8.94 Hz), 3.14 (m, 4H), 3.04 (s, 3H), 2.90 (s, 3H), 2.46 (m, 4H), 2.22 (s, 3H); HRMS (ESI) m/e calcd for C24H27N5O3 432.20411. found 432.20337 (M+H)+1, Analysis for C24H27N5O3, Calcd: C, 66.50; H, 6.28; N, 16.16. Found: C, 66.33; H, 6.43; N, 16.28.

Provenance & Evidence