N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamine → 5-((3,5-dichloropyridin-4-yl)thio)-N-(6-((2-(dimethylamino)ethyl)amino)pyridin-3-yl)-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]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[CH3:21][N:22]([CH3:33])[CH2:23][CH2:24][NH:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][N:27]=1>>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:32][C:29]2[CH:28]=[N:27][C:26]([NH:25][CH2:24][CH2:23][N:22]([CH3:33])[CH3:21])=[CH:31][CH:30]=2)=[O:16])=[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-carboxylic acid (200 mg, 0.57 mmol) and N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamine (113 mg, 0.63 mmol). The title compound was obtained as a yellow solid (9.0 mg, 3% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.37 (1H, br), 8.99 (2H, m), 8.61 (1H, m), 8.20 (1H, m), 7.60 (1H, m), 6.53 (2H, m), 2.65 (2H, m), 2.50 (6H, m), 2.37 (2H, m). MS m/z: 513.17, 515.17 [M+H]+.
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-2df71256b8c6451eb088e0a3d1327d05
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680139B2
Reaction notes
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