m-Chloroperbenzoic acid → [5-(3-Chloro-5-fluoro-phenyl)-1-(2-methyl-4-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

HRID 930059Notes

Reaction equation

HRID 930059 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=3)[N:12]=[C:11]([C:21]([N:23]3[CH2:27][CH2:26][S:25][CH2:24]3)=[O:22])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=C(C2N(C3C=NC=CC=3)N=C(C(N3CCS(=O)C3)=[O:48])C=2)C=C(F)C=1.ClC1C=CC=C(C(OO)=O)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=3)[N:12]=[C:11]([C:21]([N:23]3[CH2:27][CH2:26][S:25](=[O:48])[CH2:24]3)=[O:22])[CH:10]=2)[CH:5]=[C:6]([F:8])[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 86574284[5-(3-Chloro-5-fluoro-phenyl)-1-(2-methyl-4-pyridyl)pyrazol-3-yl]-thiazolidin-3-yl-methanone

Product 1

HCID 86574285[5-(3-Chloro-5-fluoro-phenyl)-1-(2-methyl-4-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

Procedure

55 mg (0.14 mmol) of the compound of Example 23 is reacted analogously to the synthesis of the compound of Example 6 with 34 mg (0.14 mmol, 70%) of meta-chloroperbenzoic acid for 2 hours at room temperature. After the crude product is purified by means of preparative HPLC (mobile solvent: acetonitrile/water gradient), 53 mg (93% 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), 53 mg (93% of theory) of the title compound
  2. customis obtained

Sources & evidence

ORD record
ord-02dc80c9699f4fbb8750474eadaf3b91
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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