(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione → HCID 178518256, compound

HRID 2236640Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[NH:17]1[CH:21]=[C:20]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[N:19]=[CH:18]1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:26][C:25]1[CH:24]=[CH:23][C:22]([C:20]2[N:19]=[CH:18][NH:17][CH:21]=2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2.00 g (7.09 mmol) of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione and 1.24 g (7.80 mmol) of 4-(1H-Imidazol-4-yl)aniline in 22 mL of N,N-dimethylformamide (DMF) is heated at 120° C. for 1.25 h. The chilled reaction mixture is filtered and the insoluble material is washed with N,N-dimethylformamide (DMF) and Et2O. In order to remove residual N,N-dimethylformamide (DMF), the solid is boiled with MeOH (2×), washed with Et2O and dried in vacuo. The yield is 2.10 g (72%) of yellow-brown crystals: mp >300° C. (dec); 1H NMR (DMSO-d6) δ 12.6 (d, 1H, J=12.7 Hz), 12.2 (s, 1H), 11.4 (s, 1H), 8.98 (d, 1H, J=12.7 Hz), 8.49 (s, 1H), 7.86 (m, 3H), 7.67 (m, 4H), 7.41 (d, 1H, J=8.34 Hz); HRMS (ESI) m/e calcd for C19H13BrN4O2 409.02947. found 409.02902 (M+H)+1.

Workup

customThe chilled reaction mixture
filtrationis filtered
washthe insoluble material is washed with N,N-dimethylformamide (DMF) and Et2O
customIn order to remove residual N,N-dimethylformamide (DMF)
washwashed with Et2O
customdried in vacuo

Sources & evidence

ORD record: ord-6301f9a06a5946ce8ad694b8bbf9417b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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