2-Aminothiazole → 4-(2-Oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamide

HRID 1696102Notes

Reaction equation

HRID 1696102 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[O:7]=[C:8]1[CH2:13][N:12]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:11][CH2:10][N:9]1[C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[O:7]=[C:8]1[CH2:13][N:12]([C:14](=[O:19])[C:15]([F:17])([F:16])[F:18])[CH2:11][CH2:10][N:9]1[C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 59465974HCID 59465974, compound

Product 1

HCID 594665024-(2-Oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamideYield 48.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Synthesized according to general procedure 12, method A. The reaction was set up with 2-aminothiazole (2.4 g, 24.2 mmol), anhydrous pyridine (10 mL), and 4-(2-oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)benzene-1-sulfonyl chloride (9.0 g, 24.2 mmol). The dark oil was purified via silica gel chromatography using 5% MeOH in CH2Cl2 followed by a second purification on silica gel using 80% EtOAc in hexanes to obtain the desired sulfonamide as a white solid (5.1 g, 11.7 mmol, 48% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=435.2; tR=2.35 min.

Workup

  1. customSynthesized
  2. customThe dark oil was purified via silica gel chromatography
  3. customfollowed by a second purification on silica gel using 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-6ed15124175b42b98026578f13faa98f
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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