3-Pyridinemethanamine → 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

HRID 1192122Notes

Reaction equation

HRID 1192122 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].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH2:28])[CH:22]=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:28][CH2:27][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 310183-PyridinemethanamineHCID 602073375-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride

Product 1

HCID 602073385-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(pyridin-3-ylmethyl)thiophene-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 3-picolylamine (35 mg, 0.32 mmol). The title compound was obtained as a yellow solid (21 mg, 17% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.42 (1H, m), 8.99 (2H, s), 8.51 (1H, s), 8.47 (1H, s), 7.69 (1H, m), 7.36 (1H, m), 4.43 (2H, m). MS m/z: 441.17, 443.16 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7b1c7f589ae549c5b3af5a17c89e9818
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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