m-Chloroperbenzoic acid → [5-(3-Chloro-5-fluoro-phenyl)-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

HRID 930050Notes

Reaction equation

HRID 930050 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[N:12]=[C:11]([C:20]([N:22]3[CH2:26][CH2:25][S:24][CH2:23]3)=[O:21])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[N:12]=[C:11]([C:20]([N:22]3[CH2:26][CH2:25][S:24](=[O:35])[CH2:23]3)=[O:21])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71576534[5-(3-Chloro-5-fluoro-phenyl)-1-(3-pyridyl)pyrazol-3-yl]-thiazolidin-3-yl-methanone

Product 1

HCID 71576535[5-(3-Chloro-5-fluoro-phenyl)-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.26 mmol) of the compound of Example 5 is dissolved in 5 ml of dichloromethane, mixed with 63 mg (0.26 mmol, 70% purity) of meta-chloroperbenzoic acid, and stirred for 4 hours at room temperature. The reaction mixture is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). 97 mg (93% of theory) of the title compound is obtained.

Workup

  1. customThe reaction mixture is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-645cd2a4759a43d18a361871f33a8167
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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