Ammonia → HCID 67549316, compound

HRID 1352354Notes

Reaction equation

HRID 1352354 reaction equation
C1(S([CH:10]2[CH:12]([C:13]([F:16])([F:15])[F:14])O2)(=O)=O)C=CC=CC=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30](=[S:32])[NH2:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].N1(C(OC(C)(C)C)=O)CCNCC1.C(N1C=CN=C1)(N1C=CN=C1)=S.N>CN(C)C=O>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:30]2[S:32][C:12]([C:13]([F:14])([F:15])[F:16])=[CH:10][N:31]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylateHCID 211002182-(Benzenesulfonyl)-3-(trifluoromethyl)oxirane

Product 1

HCID 67549316HCID 67549316, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 17.5 mmol 2-benzenesulfonyl-3-trifluoromethyl-oxirane in 20 ml N,N-dimethylformamide was added 15.9 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). The mixture was heated at 90° C. for 10 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 an orange crystalline solid (yield 26%). MS (m/e): 338.1 (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-eddb781fa26e4d88b48c42e1c0bcecc0
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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