Sodium Bicarbonate → 10-Bromo-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 545011Notes

Reaction equation

C([O-])(O)=O.[Na+].[Br:6][C:7]1[CH:23]=[CH:22][C:10]2[NH:11][C:12](=[O:21])[CH2:13][C:14](=[CH:17]N(C)C)[C:15](=O)[C:9]=2[CH:8]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([NH:34][C:35]([NH2:37])=[NH:36])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]>>[Br:6][C:7]1[CH:23]=[CH:22][C:10]2[NH:11][C:12](=[O:21])[CH2:13][C:14]3[CH:17]=[N:37][C:35]([NH:34][C:28]4[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=4)=[N:36][C:15]=3[C:9]=2[CH:8]=1

Participants

Reactant 3

HCID 516892Sodium Bicarbonate

HCID 66934668HCID 66934668, compound

HCID 178492306N-(3,4-dimethoxyphenyl)guanidine

Product 1

HCID 5985115610-Bromo-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Procedure

In a manner similar to method I (NaHCO3 used instead of K2CO3), 7-bromo-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-k) and 1-(3,4-dimethoxyphenyl)-guanidine were converted to I-18 (74%): HRMS Calcd. for C20H17BrN4O3: 441.0562, Found 441.0548.

Sources & evidence

ORD record: ord-a605e9e328ee40e6b0de32668563745f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935694B2

Reaction notes

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