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

HRID 1697736Notes

Reaction equation

HRID 1697736 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][N:6]1[C:14](=S)[CH2:15][C:16](=O)[CH3:17])=[O:4].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][N:6]1[C:14]1[N:28]([C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:30])[F:31])=[CH:27][CH:26]=2)[N:29]=[C:16]([CH3:17])[CH:15]=1)=[O:4]

Participants

3

Reactant 2

HCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 86646866(2S,4R)-4-methanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 67278243(2S,4R)-4-Methanesulfonyl-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-methanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester (example 448c) was reacted with 4-(trifluoromethyl)phenylhydrazine (CAS Reg. No. 368-90-1) to give the title compound. MS (ESI): m/z=432.0 [M+H]+.

Sources & evidence

ORD record
ord-949733d0453c4faeb6ad454dfe8f9a35
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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