7-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione → 10-Chloro-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 2373398Notes

Reaction equation

HRID 2373398 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[CH2:8][C:9](=[CH:12]N(C)C)[C:10](=O)[C:4]=2[CH:3]=1.[N+]([O-])(O)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:33][C:34]([NH2:36])=[NH:35])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[CH2:8][C:9]3[CH:12]=[N:36][C:34]([NH:33][C:27]4[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=4)=[N:35][C:10]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 669347277-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneHCID 178492307HCID 178492307, compound

Product 1

HCID 5985135510-Chloro-2-(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, 7-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-d) and N-(3,4-dimethoxyphenyl)guanidine nitrate were converted to I-24 (67%): HRMS Calcd. for C20H17ClN4O3: 397.1067, Found 397.1059.

Sources & evidence

ORD record
ord-d18920d895a14afd940a76b9a34b2ff8
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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