Triethylamine → 5-Chloro-N-(2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)thiophene-2-sulfonamide

HRID 748046Notes

Reaction equation

HRID 748046 reaction equation
[CH2:1]([CH:3]([CH2:21][CH3:22])[CH:4]([NH2:20])[C:5]1[N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[N:8]=[CH:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[Cl:30][C:31]1[S:35][C:34]([S:36](Cl)(=[O:38])=[O:37])=[CH:33][CH:32]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:30][C:31]1[S:35][C:34]([S:36]([NH:20][CH:4]([C:5]2[N:9]([S:10]([C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)(=[O:12])=[O:11])[N:8]=[CH:7][CH:6]=2)[CH:3]([CH2:1][CH3:2])[CH2:21][CH3:22])(=[O:38])=[O:37])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 68593832(2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)amine

Product 1

HCID 112142375-Chloro-N-(2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)thiophene-2-sulfonamideYield 33%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To (2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)amine (0.200 g, 0.630 mmol) in CH2Cl2 (10 mL) was added triethylamine (0.18 mL, 1.3 mmol) and 5-chlorothiophene-2-sulfonyl chloride (0.14, 0.76 mmol) After 1 day the reaction mixture was diluted with chloroform (30 mL), washed with H2O (2×30 mL), dried (Na2SO4) and concentrated. Column chromatography (EtOAc/hexane, 3:7) provided 5-chloro-N-(2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)thiophene-2-sulfonamide (0.104 g, 33%) as a white solid (mp=146-148° C.).

Workup

  1. washwashed with H2O (2×30 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fe5fd333aae843498f7e3c5583719d99
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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