4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione → 2-(3,4-Dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 545022Notes

Reaction equation

HRID 545022 reaction equation
CN([CH:4]=[C:5]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[C:6]1=O)C.[N+]([O-])(O)=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([NH:32][C:33]([NH2:35])=[NH:34])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([NH:32][C:33]2[N:35]=[CH:4][C:5]3[CH2:11][C:10](=[O:12])[NH:9][C:8]4[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=4[C:6]=3[N:34]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 669347634-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneHCID 178492307HCID 178492307, compound

Product 1

HCID 569464812-(3,4-Dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Procedure

In a manner similar to that described for method I, 4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-c) and N-(3,4-dimethoxyphenyl)guanidine nitrate were converted to I-27 (58%): HRMS Calcd. for C20H18N4O3: 363.1457, Found 363.1441.

Sources & evidence

ORD record
ord-f9eb3c0286bd4448a4864d3a081c9e30
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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