2-(Aminomethyl)-5-methylpyrazine → 5-((3,5-dichloropyridin-4-yl)thio)-N-((5-methylpyrazin-2-yl)methyl)-4-nitrothiophene-2-carboxamide

HRID 1192124Notes

Reaction equation

HRID 1192124 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].[NH2:21][CH2:22][C:23]1[CH:28]=[N:27][C:26]([CH3:29])=[CH:25][N:24]=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:21][CH2:22][C:23]2[CH:28]=[N:27][C:26]([CH3:29])=[CH:25][N:24]=2)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 602073375-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride

Product 1

HCID 602073405-((3,5-dichloropyridin-4-yl)thio)-N-((5-methylpyrazin-2-yl)methyl)-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 (150 mg, 0.41 mmol) and 2-(aminomethyl)-5-methyl-pyrazine (60 mg, 0.49 mmol). The title compound was obtained as a solid (40 mg, 23% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.48 (1H, m), 8.98 (2H, s), 8.48 (1H, s), 8.47 (2H, m), 4.50 (2H, m), 2.50 (3H, s). MS m/z: 454.00, 456.04 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5bc31e60d7a9461bbb0f9c65e4420f56
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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