Hydrogen Peroxide → N2-(2-chloro-4-(methylcarbamoyl)phenyl)-N2-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,9-dicarboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[CH:5]=[CH:4][C:3]=1[N:12]([CH3:31])[C:13]([C:15]1[S:30][C:18]2[C:19]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:20]=3[O:21][CH2:22][CH2:23][C:17]=2[CH:16]=1)=[O:14].C(=O)([O-])[O-:33].[K+].[K+].OO>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[CH:5]=[CH:4][C:3]=1[N:12]([CH3:31])[C:13]([C:15]1[S:30][C:18]2[C:19]3[CH:27]=[C:26]([C:28]([NH2:29])=[O:33])[CH:25]=[CH:24][C:20]=3[O:21][CH2:22][CH2:23][C:17]=2[CH:16]=1)=[O:14]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-(2-chloro-4-(methylcarbamoyl)phenyl)-9-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide 298 (100 mg) and potassium carbonate (37 mg) in DMSO (3 mL) at 0° C. was added hydrogen peroxide (30 μL of a 33% solution in water). The reaction was stirred at room temperature for 16 h. Water was then added and the resulting solid collected by filtration and air-dried to give 306. NMR: (DMSO): 2.81 (3H, d, J 4.5, Me), 2.91-2.93 (2H, m), 3.68 (3H, s, Me), 4.19-4.22 (2H, m), 6.41 (1H, s, NH), 7.03 (1H, d, J 8.4, Ar), 7.35 (1H, s), 7.71-7.77 (2H, m, Ar), 7.92 (1H, dd, J 8.3 and 2.0, Ar), 8.03-8.05 (3H, m) and 8.65-8.67 (1H, m). MS: (ESI+) MH+ 469.35
Workup
- filtrationthe resulting solid collected by filtration
- customair-dried
Sources & evidence
- ORD record
- ord-10b522df6c2d472ebeb55fe2ca44c9ce
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309265B2
Reaction notes
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