Pyrazole → (5-Methanesulfonyl-2-pyrazol-1-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 32764

Reaction equation

HRID 32764 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].[NH:30]1[CH:34]=[CH:33][CH:32]=[N:31]1.C(=O)([O-])[O-].[K+].[K+].N[C@@H]1CCCC[C@H]1N>[Cu]I.O1CCOCC1>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:30]2[CH:34]=[CH:33][CH:32]=[N:31]2)=[C:3]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 59793691(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 68842692(5-Methanesulfonyl-2-pyrazol-1-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneYield 21%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

In a tube were added successively (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (compound CK, 0.1 g, 0.19 mmol), pyrazole (15 mg, 0.223 mmol), potassium carbonate (51 mg, 0.37 mmol), CuI (7 mg, 0.037 mmol), Trans-1,2-diaminocyclohexane (9 ul, 0.07 mmol) and dioxane (0.4 ml). The mixture was heated under argon at 120° C. for 24 hours. The reaction mixture was cooled to room temperature and quenched with water/dichloromethane. The aqueous layer was extracted twice with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: heptane/ethylacetate: 0-5% to provide the title compound as a light grey powder (19 mg, 21%), MS (m/e): 479.1 (M+H, 100%)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water/dichloromethane
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was chromatographed over silicagel

Sources & evidence

ORD record
ord-ad4e2d4c03f94ba8978a197bf2cb149c
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Linked notes

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