Diisopropylethylamine → N-[2-(3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazol-1-yl)ethyl]-3-(trifluoromethyl)benzenesulfonamide

HRID 1016609Notes

Reaction equation

HRID 1016609 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:5]1.C(N(C(C)C)CC)(C)C.[F:31][C:32]([F:44])([F:43])[C:33]1[CH:34]=[C:35]([S:39](Cl)(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=1>C(#N)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:6]2[CH:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:8][N:4]([CH2:3][CH2:2][NH:1][S:39]([C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:31])([F:43])[F:44])[CH:34]=3)(=[O:41])=[O:40])[N:5]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 18407264HCID 18407264, compound

Product 1

HCID 11627589N-[2-(3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazol-1-yl)ethyl]-3-(trifluoromethyl)benzenesulfonamideYield 46.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part C: To a solution of 1-(2-aminoethyl)-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (0.56 gram, 1.87 mmol) and diisopropylethylamine in acetonitrile (20 ml) was added 3-(trifluoromethyl)phenylsulfonyl chloride (0.35 ml, 2.18 mmol) and the resulting solution was stirred at room temperature for 20 minutes. After concentration in vacuo the residue was dissolved in ethylacetate and washed with 2 N sodium hydroxide solution. The ethylacetate layer was concentrated in vacuo. The resulting oil was crystallised from a small amount of diisopropyl ether to afford crystalline N-[2-(3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazol-1-yl)ethyl]-3-(trifluoromethyl)benzenesulfonamide (0.44 gram, 46% yield). Melting point: 94-96° C.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. dissolutionwas dissolved in ethylacetate
  3. washwashed with 2 N sodium hydroxide solution
  4. concentrationThe ethylacetate layer was concentrated in vacuo
  5. customThe resulting oil was crystallised from a small amount of diisopropyl ether

Sources & evidence

ORD record
ord-7aaa8b75887246e0b5ec1bf20e859407
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

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