m-Chloroperbenzoic acid → [5-[3-Bromo-5-(trifluoromethoxy)phenyl]-1-(6-chloro-3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

HRID 930067Notes

Reaction equation

HRID 930067 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:16]=[C:15]([C:25]([N:27]3[CH2:31][CH2:30][S:29][CH2:28]3)=[O:26])[CH:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[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>>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:16]=[C:15]([C:25]([N:27]3[CH2:31][CH2:30][S:29](=[O:52])[CH2:28]3)=[O:26])[CH:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:10])([F:11])[F:12])[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 86574252[5-[3-Bromo-5-(trifluoromethoxy)phenyl]-1-(6-chloro-3-pyridyl)pyrazol-3-yl]-thiazolidin-3-yl-methanone

Product 1

HCID 86574253[5-[3-Bromo-5-(trifluoromethoxy)phenyl]-1-(6-chloro-3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

Procedure

38 mg (0.07 mmol) of the compound of Example 36 is reacted analogously to the synthesis of the compound of Example 6 with 18 mg (0.07 mmol, 70%) of meta-chloroperbenzoic acid for 72 hours at room temperature. After the crude product is purified by means of preparative HPLC (mobile solvent: acetonitrile/water gradient), 31 mg (79% of theory) of the title compound is obtained.

Workup

  1. customAfter the crude product is purified by means of preparative HPLC (mobile solvent: acetonitrile/water gradient), 31 mg (79% of theory) of the title compound
  2. customis obtained

Sources & evidence

ORD record
ord-726ee56e8e104a7bb06174a1db4d33be
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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