4-(1-tert-butyl-3-(4-chlorobenzyl)-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)benzenesulfonamide → 4-(3-(4-Chlorobenzyl)-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)benzenesulfonamide

HRID 1644640Notes

Reaction equation

HRID 1644640 reaction equation
C([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:8][C:7]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[N:6]1)(C)(C)C>C(O)=O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C:7]2[CH:8]=[C:9]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([S:17]([NH:20][C:21]4[S:22][CH:23]=[CH:24][N:25]=4)(=[O:18])=[O:19])=[CH:15][CH:16]=3)[NH:5][N:6]=2)=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 252041014-(1-tert-butyl-3-(4-chlorobenzyl)-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 1785275544-(3-(4-Chlorobenzyl)-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)benzenesulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 4-[2-tert-butyl-5-(4-chloro-benzyl)-2H-pyrazol-3-ylamino]-N-thiazol-2-yl-benzenesulfonamide (20 mg, 0.04 mmol, 1.0 equiv) was heated in 1.0 mL of formic acid at 95° C. After 16 h, the reaction mixture was concentrated in vacuo. The residue was purified via automated flash chromatography (4 g SiO2, gradient from chloroform to 12% methanol in chloroform) to afford the product as an off-white solid (7 mg, 40%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-3b9dd1ab0d8d4dd49a1b0433677c45cc
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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