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

HRID 2373390Notes

Reaction equation

HRID 2373390 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.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:22][CH:21]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:28]=[C:27]([NH:26][C:23]4[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][CH:24]=4)[N:29]=[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 178512500HCID 178512500, compound

Product 1

HCID 598510759-Chloro-2-(4-chloro-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

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 1-(4-chlorophenyl)guanidine were converted to I-11 (23%): HRMS Calcd. for C18H12Cl2N4O: 371.0466, Found 371.0471.

Sources & evidence

ORD record
ord-9ed407c2abde45aeb0189da4dfd16e60
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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