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

HRID 2373396Notes

Reaction equation

HRID 2373396 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)[C:10](=[CH:13]N(C)C)[CH2:9][C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1.[NH:19]([CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:20]([NH2:22])=[NH:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:21]=[C:20]([NH:19][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[N:22]=[CH:13][C:10]=3[CH2:9][C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1

Participants

3

Reactant 2

HCID 669348778-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneHCID 178512977gamma-Guanidinobutyric acid

Product 1

HCID 598514224-(9-Chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-butyric acid

Procedure

In a manner similar to that described for method I, 8-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-j) and 4-guanidino butyric acid were converted to I-19 (6%): HRMS Calcd. for C16H15ClN4O3: 347.091, Found 347.092.

Sources & evidence

ORD record
ord-54f66b8bb3ed40b3b602e36df9348343
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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