Chloroform → 2-(2-Chlorophenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid 3-methanesulfonyl-benzylamide

HRID 1672998Notes

Reaction equation

HRID 1672998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13](Cl)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1.C(Cl)(Cl)Cl.[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32])(=[O:27])=[O:26]>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH:32][C:13]([C:12]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=[O:14])(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 2760937(3-(Methylsulfonyl)phenyl)methanamineHCID 574582382-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

Product 1

HCID 592403552-(2-Chlorophenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid 3-methanesulfonyl-benzylamideYield 21%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a round bottom flask was added 2-(2-chlorophenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride (160 mg, 0.520 mmol) in a solution of anhydrous CHCl3 (10 mL). To the reaction solution was added 3-methylsulfonyl benzylamine (122 mg, 0.661 mmol), TEA (150 μL, 1.10 mmol), and DMAP (67 mg, 0.549 mmol). The reaction solution was allowed to stir at 60° C. for 5 hrs. The reaction solution was diluted with EtOAc (150 mL), poured into a separatory funnel and washed with aq. NH4Cl. The partitioned organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure on the rotavapor. The crude material was chromatographed through a silica gel column using a solvent gradient of 100% hexane to 30% EtOAc to afford 50 mg of title compound (20%). 1H NMR (CDCl3): δ 7.83 (m, 1H), 7.79 (s, 1H), 7.48-7.58 (m, 4H), 7.42-7.46 (m, 2H), 7.05 (s, 1H), 6.66 (t, J=6 Hz, 1H), 4.58 (d, J=6 Hz, 2H), 3.03 (s, 3H); MS (ES): 458.1 [M+H]+.

Workup

  1. additionpoured into a separatory funnel
  2. washwashed with aq. NH4Cl
  3. dry with materialThe partitioned organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure on the rotavapor
  6. customThe crude material was chromatographed through a silica gel column

Sources & evidence

ORD record
ord-f3d62002827e428a8a72b9b491e5bc9d
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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