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

HRID 930084Notes

Reaction equation

HRID 930084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:16]=[C:15]([C:24]([N:26]3[CH2:30][CH2:29][S:28][CH2:27]3)=[O:25])[CH:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:39])C=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:16]=[C:15]([C:24]([N:26]3[CH2:30][CH2:29][S:28](=[O:39])[CH2:27]3)=[O:25])[CH:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:10])([F:11])[F:12])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86574657[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-thiazolidin-3-yl-methanone

Product 1

HCID 86574658[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

102 mg (0.23 mmol) of the compound of Example 59 is dissolved in 5 ml of dichloromethane, mixed with 57 mg (0.23 mmol, 70% purity) of meta-chloroperbenzoic acid, and stirred for 16 hours at room temperature. The reaction mixture is concentrated by evaporation in a rotary evaporator, mixed with some acetonitrile, filtered over a Millipore spray filter, and then separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). 87 mg (82% of theory) of the title compound is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation in a rotary evaporator
  2. additionmixed with some acetonitrile
  3. filtrationfiltered over a Millipore spray
  4. filtrationfilter
  5. customseparated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-9bfa4dea1be14214b42b143622fc6e43
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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