5-Isocyanatoisoquinoline → N-isoquinolin-5-yl-N'-[7-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-yl]urea
Reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)=[C:2]=[O:3].[F:14][C:15]([F:28])([F:27])[C:16]1[CH:25]=[C:24]2[C:19]([CH:20]([NH2:26])[CH2:21][CH2:22][O:23]2)=[CH:18][CH:17]=1>>[CH:9]1[C:10]2[C:5](=[C:4]([NH:1][C:2]([NH:26][CH:20]3[C:19]4[C:24](=[CH:25][C:16]([C:15]([F:28])([F:14])[F:27])=[CH:17][CH:18]=4)[O:23][CH2:22][CH2:21]3)=[O:3])[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][N:8]=1Participants
3
Procedure
3 ml of the 5-isocyanato-isoquinoline solution was added to the product of Example 4D (49 mg, 0.3 mmol) and stirred at ambient temperature overnight, and the precipitate formed was collected by filtration and washed with diethyl ether to give 23 mg of the title compound (23% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.63 (s, 1H), 8.55 (d, J=6.0 Hz, 1H), 8.32 (m, 1H), 7.90 (d, J=6.0 Hz, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.60 (m, 2H), 7.30-7.12 (m, 3H), 5.02 (m, 1H), 4.42-4.20 (m, 2H), 2.30-2.00 (m, 2H). MS (ESI) m/e 388 (M+H)+. Calcd. For C20H16N3O2F3.0.2; H2O: C, 62.01; H, 4.16; N, 10.85. Found: C, 61.29; H, 3.94; N, 10.64.