5-Isocyanato-3-methylisoquinoline → N-(7-tert-butyl-3,4-dihydro-2H-chromen-4-yl)-N'-(3-methylisoquinolin-5-yl)urea
Reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N:12]=[C:13]=[O:14])[CH:8]=[CH:7][CH:6]=2.[C:15]([C:19]1[CH:28]=[C:27]2[C:22]([CH:23]([NH2:29])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>>[C:15]([C:19]1[CH:28]=[C:27]2[C:22]([CH:23]([NH:29][C:13]([NH:12][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]4)=[O:14])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]Participants
3
Procedure
6 mL of the 3-methyl-5-isocyanato-isoquinoline solution was added to the product of Example 1C (123 mg, 0.6 mmol). The reaction mixture was stirred overnight, and the precipitate formed was collected by filtration and washed with diethyl ether to give 0.15 g of the title compound (64% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.17 (s, 1H), 8.46 (s, 1H), 8.34 (d, J=6.8 Hz, 1H), 7.66-7.73 (m, 2H), 7.51 (t, J=8.0 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.12 (d, J=7.1 Hz, 1H), 6.98 (dd, J=8.0, 1.9 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 4.82-4.89 (m, 1H), 4.24-4.31 (m, 1H), 4.10-4.18 (m, 1H), 2.63 (s, 3H), 1.99-2.14 (m, 2H), 1.25 (s, 9H). MS (ESI+) m/e 390 (M+H)+. Calc'd. For C24H27N3O2.0.5H2O: C, 72.34; H, 7.08; N, 10.54. Found C, 72.52; H, 7.23; N, 10.53.