Benzenemethanamine, 4-(dimethylamino)-, hydrochloride (1:1) → 5-((3,5-dichloropyridin-4-yl)thio)-N-(4-(dimethylamino)benzyl)-4-nitrothiophene-2-carboxamide

HRID 1192140Notes

Reaction equation

HRID 1192140 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].Cl.[CH3:22][N:23]([CH3:32])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=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:29][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([N:23]([CH3:32])[CH3:22])=[CH:25][CH:26]=2)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 16211837Benzenemethanamine, 4-(dimethylamino)-, hydrochloride (1:1)HCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 602073575-((3,5-dichloropyridin-4-yl)thio)-N-(4-(dimethylamino)benzyl)-4-nitrothiophene-2-carboxamide

Procedure

Prepared according to the procedure described for example 50 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (150 mg, 0.41 mmol) and 4-(dimethylamino)benzylamine hydrogen chloride salt (60.9 mg, 0.49 mmol). The title compound was obtained as a solid (70 mg, 37% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.23 (1H, m), 8.99 (2H, s), 8.46 (1H, s), 7.1 (2H, dd), 6.7 (2H, dd), 4.26 (2H, m), 2.91 (6H, s). MS m/z: 483.05, 485.03 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4801a90fb2b84e399ede8b2eb495e252
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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