Triethylamine → ethyl 1-(4-methanesulfonylaminophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylate

HRID 968328Notes

Reaction equation

HRID 968328 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]([F:21])([F:20])[F:19])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:15]=[N:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>C1COCC1>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]([C:18]([F:21])([F:20])[F:19])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:15]=[N:14]2)=[CH:11][CH:12]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2808376Ethyl 1-(4-aminophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 22288382ethyl 1-(4-methanesulfonylaminophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylateYield 15.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (80 mg) was added to a mixture of ethyl 1-(4-aminophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylate (150 mg), triethylamine (76 mg) and THF (2 ml) under ice-cooling, followed by stirring at room temperature for 4 hours. Thereafter, the same treatment of Example 2 was carried out to give ethyl 1-(4-methanesulfonylaminophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylate (29 mg) as a colorless solid.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-d03618c7383142c19f32481c347d903a
Source dataset
uspto-grants-2005_10
Patent number
US06958339B2

Reaction notes

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