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

HRID 545015Notes

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][CH:23]=[CH:22][C:21]=1[NH:26][C:27]([NH2:29])=[NH:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:28]=[C:27]([NH:26][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[Cl:19])[N:29]=[CH:13][C:10]=3[CH2:9][C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1

Participants

Reactant 2

HCID 669348778-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HCID 178512473Chlorophenylguanidine

Product 1

HCID 598512399-Chloro-2-(2-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-(2-chlorophenyl)guanidine were converted to I-12 (26%): HRMS Calcd. for C, H12Cl2N4O: 371.0466, Found 371.0467.

Sources & evidence

ORD record: ord-70e0d83f6c5340d8878f2ddd794176ba
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935694B2

Reaction notes

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