5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride → 5-((3,5-dichloropyridin-4-yl)thio)-N-(4-(methylsulfonyl)benzyl)-4-nitrothiophene-2-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14](Cl)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].Cl(O)(=O)=O.[CH3:25][S:26]([C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1)(=[O:28])=[O:27]>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:34][CH2:33][C:32]2[CH:31]=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:36][CH:35]=2)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]Participants
3
Procedure
Prepared according to the procedure described for example 50 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carbonyl chloride (100 mg, 0.27 mmol) and 4-methylsulfonyl-benzylamine hydrogen chloric acid salt (59 mg, 0.32 mmol). The title compound was obtained as a yellow solid (54 mg, 39% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.51 (1H, m), 8.99 (2H, s), 8.48 (1H, s), 7.89 (2H, dd), 7.55 (2H, dd), 4.51 (2H, m), 3.18 (3H, s). MS m/z: 515.97, 517.99 [M+H]+.
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-ee1950fcb89441e79276fcc814bae183
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680139B2
Reaction notes
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