4-(Trifluoromethyl)phenylhydrazine → (2S,4R)-4-Cyclopropylmethanesulfonyl-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697752Notes

Reaction equation

HRID 1697752 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17](=S)[CH2:18][C:19](=O)[CH3:20])=[O:4].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17]1[N:31]([C:28]2[CH:27]=[CH:26][C:25]([C:24]([F:23])([F:33])[F:34])=[CH:30][CH:29]=2)[N:32]=[C:19]([CH3:20])[CH:18]=1)=[O:4]

Participants

3

Reactant 2

HCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 86646864(2S,4R)-4-Cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 67278369(2S,4R)-4-Cyclopropylmethanesulfonyl-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-4-cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester (example 445c) was reacted with 4-(trifluoromethyl)phenylhydrazine (CAS Reg. No. 368-90-1) to give the title compound as brown solid. MS (ESI): m/z=472.6 [M+H]+.

Sources & evidence

ORD record
ord-5f7c4fce82324a91aee89cdfe88fba3c
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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