Benzenesulfonyl chloride, 2,4-dichloro- → HCID 57718221, compound

HRID 1984605Notes

Reaction equation

HRID 1984605 reaction equation
[CH2:1]([O:6][C:7](=[O:31])[C:8]1[C:13]([S:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:12][N:11]=[C:10]([NH2:30])[CH:9]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[S:40](Cl)(=[O:42])=[O:41]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH2:1]([O:6][C:7](=[O:31])[C:8]1[C:13]([S:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:12][N:11]=[C:10]([NH:30][S:40]([C:34]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:33]=2[Cl:32])(=[O:42])=[O:41])[CH:9]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 577182132-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester

Product 1

HCID 57718221HCID 57718221, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of the 2-amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester (500 mg, 1.1 mmol), 2,4-dichlorobenzenesulfonylchloride (327 mg, 1.33 mmol) and 4-dimethylaminopyridine (134 mg, 1.1 mmol) in pyridine (10 ml) was stirred at 40° C. overnight. The pyridine was removed under reduced pressure and the residue purified by flash column chromatography using ethyl acetate 1/2 hexane as eluent to afford 2-(2,4-dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester as a yellow foam (217 mg, 29%).

Workup

  1. customThe pyridine was removed under reduced pressure
  2. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-61d94ac5175d4057b16fa616cc461a4e
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

Loading…