5-Chloro-4-nitrothiophene-2-sulfonyl chloride → 5-((3,5-dichloropyridin-4-yl)thio)-N-(1-methylpiperidin-4-yl)-4-nitrothiophene-2-sulfonamide

HRID 1192253Notes

Reaction equation

HRID 1192253 reaction equation
Cl[C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Na].[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[SH:22].[CH3:24][N:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1>>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[S:22][C:2]1[S:6][C:5]([S:7]([NH:31][CH:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)(=[O:9])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chlorideHCID 27375314-Amino-1-methylpiperidineHCID 178527724HCID 178527724, compound

Product 1

HCID 602074725-((3,5-dichloropyridin-4-yl)thio)-N-(1-methylpiperidin-4-yl)-4-nitrothiophene-2-sulfonamide

Procedure

Prepared according to the procedure described for step B of example 17 and step B of example 44 from 5-chloro-4-nitrothiophene-2-sulfonyl chloride (0.26 g, 1 mmol), 3,5-dichloropyridine-4-thiol sodium salt (0.18 g, 1.0 mmol) and 1-methylpiperidin-4-amine (0.55 g, 5.0 mmol). The title product was obtained as oil (2.0 mg, 0.4% yield). MS m/z: 482.97, 484.97 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b13e3f3fdf3242d4b17103cdd45090f5
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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