4-Fluorobenzylamine → 5-((3,5-dichloropyridin-4-yl)thio)-N-(4-fluorobenzyl)-4-nitrothiophene-2-carboxamide

HRID 1192128Notes

Reaction equation

HRID 1192128 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].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1>>[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:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=2)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 602073375-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride

Product 1

HCID 674947085-((3,5-dichloropyridin-4-yl)thio)-N-(4-fluorobenzyl)-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-carbonyl chloride (100 mg, 0.27 mmol) and 4-fluorobenzylamine (40 mg, 0.32 mmol). The title compound was obtained as a solid (60 mg, 48% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.37 (1H, m), 9.03 (2H, s), 8.46 (1H, s), 7.32 (2H, dd), 7.20 (2H, dd), 4.43 (2H, m). MS m/z: 456.04, 458.00 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7095c28f1ec047d78d4ba7f456d9e988
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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