1-benzyl-8-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione → 4-(7-Benzyl-9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzoic acid

HRID 544993Notes

Reaction equation

HRID 544993 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][C:12](=[CH:16]N(C)C)[C:11](=O)[C:10]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]([C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)[C:27]([NH2:29])=[NH:28]>>[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][C:12]2[CH:16]=[N:28][C:27]([NH:26][C:30]3[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=3)=[N:29][C:11]=2[C:10]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 669345481-benzyl-8-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneHCID 178512548HCID 178512548, compound

Product 1

HCID 598515674-(7-Benzyl-9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzoic acid

Procedure

In a manner similar to that described for method I, 1-benzyl-8-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-n) and 4-guanidinobenzoic acid were converted to I-6 (26%): MS m/z=471 (M+H) HRMS Calcd. for C26H19ClN4O3: 471.1223, Found 471.1310.

Sources & evidence

ORD record
ord-0ff526cf66934f47b1ffb703471f80b0
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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