Methylhydrazine → (2S,4R)-1-[1-Methyl-5-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697668Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23](=S)[CH2:24][C:25](=O)[CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:4].[CH3:34][NH:35][NH2:36]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23]1[CH:24]=[C:25]([CH:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[N:35]([CH3:34])[N:36]=1)=[O:4]

Participants

Reactant 2

HCID 6061Methylhydrazine

HCID 86646857(2S,4R)-1-[3-oxo-3-(tetrahydro-pyran-4-yl)-thiopropionyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66772551(2S,4R)-1-[1-Methyl-5-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-1-[3-oxo-3-(tetrahydro-pyran-4-yl)-thiopropionyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with methylhydrazine (CAS Reg. No. 60-34-4) to give the title compound as colorless foam. MS (ESI): m/z=502.2 [M+H]+.

Sources & evidence

ORD record: ord-26837cb48de14f438de075c186e7723b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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