4-Dimethylaminomethylene-8-methyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione → 2-(3,4-Dimethoxy-phenylamino)-9-methyl-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 2373431Notes

Reaction equation

HRID 2373431 reaction equation
CN([CH:4]=[C:5]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:7]=2[C:6]1=O)C.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([NH:29][C:30]([NH2:32])=[NH:31])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([NH:29][C:30]2[N:32]=[CH:4][C:5]3[CH2:11][C:10](=[O:12])[NH:9][C:8]4[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:7]=4[C:6]=3[N:31]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

3

Reactant 2

HCID 669345664-Dimethylaminomethylene-8-methyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneHCID 178492306N-(3,4-dimethoxyphenyl)guanidine

Product 1

HCID 569464832-(3,4-Dimethoxy-phenylamino)-9-methyl-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Procedure

In a manner similar to method I, 4-((dimethylamino)methylene)-8-methyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-g) and 1-(3,4-dimethoxyphenyl)guanidine were converted to I-42 (57%): HRMS Calcd. for C21H20N4O3: 377.1613, Found 377.1613.

Sources & evidence

ORD record
ord-bfb6828c70d9458fb88e367cc98ed067
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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