m-Chloroperbenzoic acid → [5-[3-Fluoro-5-(2,2,2-trifluoroethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

HRID 930088Notes

Reaction equation

HRID 930088 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[N:18]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:17]=[C:16]([C:25]([N:27]3[CH2:31][CH2:30][S:29][CH2:28]3)=[O:26])[CH:15]=2)[CH:5]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:7]=1.ClC1C=C(C2N(C3C=NC=CC=3)N=C(C(N3CCS(=O)C3)=[O:52])C=2)C=C(F)C=1.ClC1C=CC=C(C(OO)=O)C=1>>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[N:18]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:17]=[C:16]([C:25]([N:27]3[CH2:31][CH2:30][S:29](=[O:52])[CH2:28]3)=[O:26])[CH:15]=2)[CH:5]=[C:6]([O:8][CH2:9][C:10]([F:12])([F:11])[F:13])[CH:7]=1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 71576535[5-(3-Chloro-5-fluoro-phenyl)-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanoneHCID 86574680[5-[3-Fluoro-5-(2,2,2-trifluoroethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-thiazolidin-3-yl-methanone

Product 1

HCID 86574681[5-[3-Fluoro-5-(2,2,2-trifluoroethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

Procedure

44 mg (0.10 mmol) of the compound of Example 72 is reacted analogously to the synthesis of the compound of Example 6 with 24 mg (0.10 mmol, 70%) of meta-chloroperbenzoic acid overnight at room temperature. The crude product is filtered over a Millipore spray filter and separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). 35 mg (77% of theory) of the title compound is obtained.

Workup

  1. filtrationThe crude product is filtered over a Millipore spray
  2. filtrationfilter
  3. customseparated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-ec876727ef664c71aa1dc002743220a8
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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