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

HRID 545013Notes

Reaction equation

HRID 545013 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.[OH:19][CH2:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]([NH2:30])=[NH:29])[CH:24]=[CH:25][CH:26]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:29]=[C:28]([NH:27][C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][OH:19])[CH:22]=4)[N:30]=[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 178512491N-[3-(Hydroxymethyl)phenyl]guanidine

Product 1

HCID 598511009-Chloro-2-(3-hydroxymethyl-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]-azepine-6-one

Procedure

In a manner similar to method I, 8-chloro-4-((dimethylamino)methylene)-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-j) and 1-(3-(hydroxymethyl)phenyl)-guanidine were converted to I-79 (51%): HRMS Calcd. for C19H15ClN4O2: 367.0961, Found 367.0973.

Sources & evidence

ORD record
ord-ff53d2ee4c334b1b8ed984256b47276f
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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