Piperidine-1-propylamine → 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-(piperidin-1-yl)propyl)thiophene-2-carboxamide

HRID 1192121Notes

Reaction equation

HRID 1192121 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([CH2:27][CH2:28][CH2:29][NH2:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]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:30][CH2:29][CH2:28][CH2:27][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 19049Piperidine-1-propylamineHCID 602073375-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride

Product 1

HCID 602073365-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-(piperidin-1-yl)propyl)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-(piperidine-1-yl)propylamine (46 mg, 0.32 mmol). The title compound was obtained as a solid (50 mg, 39% 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: 475.09, 477.08 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-54fb64a81e5e49fea2aa3eda7171a7aa
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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