Potassium Carbonate → 9-Chloro-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 544996Notes

Reaction equation

HRID 544996 reaction equation
C([O-])(O)=O.[Na+].C([O-])([O-])=O.[K+].[K+].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[C:22](=O)[C:21](=[CH:24]N(C)C)[CH2:20][C:19](=[O:28])[NH:18][C:17]=2[CH:29]=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([NH:40][C:41]([NH2:43])=[NH:42])[CH:35]=[CH:36][C:37]=1[O:38][CH3:39]>CCO.CN(C=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[C:22]3[N:42]=[C:41]([NH:40][C:34]4[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:32]([O:31][CH3:30])[CH:33]=4)[N:43]=[CH:24][C:21]=3[CH2:20][C:19](=[O:28])[NH:18][C:17]=2[CH:29]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 669348778-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dioneHCID 178492306N-(3,4-dimethoxyphenyl)guanidine

Product 1

HCID 115021439-Chloro-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

In a manner similar to method I (DMF and NaHCO3 were used in place of EtOH and K2CO3), 8-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]-azepine-2,5-dione (v-j) and 1-(3,4-dimethoxyphenyl)guanidine were converted to I-2 (87%): HRMS Calcd. for C20H17ClN4O3: 397.1067, Found 397.109.

Sources & evidence

ORD record
ord-607c04d0e6084e69b375fedab476d49d
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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