Dimethyl Sulfoxide → 4-(4-Phenyl-1,3-thiazol-2-yl)-N-{4-[(trifluoroacetyl)amino]phenyl}piperazine-1-carboxamide

HRID 2263248Notes

Reaction equation

HRID 2263248 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[CH:8][CH:7]=1)=[O:4].[C:23]1([C:29]2[N:30]=[C:31]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[S:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:23]1([C:29]2[N:30]=[C:31]([N:34]3[CH2:39][CH2:38][N:37]([C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:21])[F:22])=[CH:11][CH:10]=4)=[O:20])[CH2:36][CH2:35]3)[S:32][CH:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 866255142,2,2-Trichloroethyl {4-[(trifluoroacetyl)amino]phenyl}carbamate

Product 1

HCID 866255164-(4-Phenyl-1,3-thiazol-2-yl)-N-{4-[(trifluoroacetyl)amino]phenyl}piperazine-1-carboxamideYield 39.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl {4-[(trifluoroacetyl)amino]phenyl}carbamate (200 mg, 0.527 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (129 mg, 0.527 mmol), diisopropylethylamine (0.184 ml, 1.05 mmol) and dimethyl sulfoxide (4 ml) was stirred at 70° C. for 24 hours, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to give 100 mg (39.8%) of the desired product as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b782615168aa4bf49b8d20e2ab35b688
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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