Ammonia → 4-(4-Methyl-5-trifluoromethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1352388Notes

Reaction equation

HRID 1352388 reaction equation
C1(S([C:10]2([CH3:17])[CH:12]([C:13]([F:16])([F:15])[F:14])O2)(=O)=O)C=CC=CC=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31](=[S:33])[NH2:32])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].N1(C(OC(C)(C)C)=O)CCNCC1.C(N1C=CN=C1)(N1C=CN=C1)=S.N>CN(C)C=O>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH2:27][N:28]([C:31]2[S:33][C:12]([C:13]([F:14])([F:15])[F:16])=[C:10]([CH3:17])[N:32]=2)[CH2:29][CH2:30]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylateHCID 21100322Rac-2-benzenesulfonyl-2-methyl-3-trifluoromethyl-oxirane

Product 1

HCID 675490954-(4-Methyl-5-trifluoromethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.92 mmol rac-2-benzenesulfonyl-2-methyl-3-trifluoromethyl-oxirane and 5.41 mmol 4-thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl 1-piperazinecarboxylate, 1,1′-thiocarbonyldiimidazole and ammonia according to the procedure of J. Med. Chem. 1998, 41, 5037–5054) in 15 ml N,N-dimethylformamide was heated at 100° C. for 4.5 h. The reaction mixture was then concentrated in vacuo and the residue purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a yellow crystalline solid (yield 30%). MS (m/e): 352.3 (M+H+, 100%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-9f93426f2dda44939ca79042dca1d975
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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