Lawesson's reagent → (2S,4R)-1-[5-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697643Notes

Reaction equation

HRID 1697643 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](=O)[CH2:24][C:25]([CH:27]1[CH2:29][CH2:28]1)=O)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.[F:53][C:54]([F:64])([F:63])[C:55]1[CH:60]=[CH:59][C:58]([NH:61][NH2:62])=[CH:57][CH:56]=1>>[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:20])([F:21])[F:22])(=[O:11])=[O:12])[CH2:7][N:6]1[C:23]1[N:61]([C:58]2[CH:57]=[CH:56][C:55]([C:54]([F:63])([F:64])[F:53])=[CH:60][CH:59]=2)[N:62]=[C:25]([CH:27]2[CH2:28][CH2:29]2)[CH:24]=1)=[O:4]

Participants

4

Reactant 3

HCID 87949Lawesson's reagentHCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 86646850(2S,4R)-1-(3-Cyclopropyl-3-oxo-propionyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646851(2S,4R)-1-[5-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-2H-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-cyclopropyl-3-oxo-propionyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with was reacted with Lawesson's reagent (CAS Reg. No. 19172-47-5) and 4-(trifluoromethyl)phenylhydrazine (CAS Reg. No. 368-90-1) to give the title compound as yellow oil.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-60b1851f5949400699c8971dc5eac981
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…