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

HRID 930064Notes

Reaction equation

HRID 930064 reaction equation
[Br: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=C(C2N(C3C=NC=CC=3)N=C(C(N3CCS(=O)C3)=[O:51])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][CH:21]=[CH:22][CH:23]=3)[N:16]=[C:15]([C:24]([N:26]3[CH2:30][CH2:29][S:28](=[O:51])[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 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 86574477[5-[3-Bromo-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-thiazolidin-3-yl-methanone

Product 1

HCID 86574478[5-[3-Bromo-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-(1-oxo-1,3-thiazolidin-3-yl)methanone

Procedure

97 mg (0.19 mmol) of the compound of Example 30 is reacted overnight analogously to the synthesis of the compound of Example 6 with 48 mg (0.19 mmol, 70%) of meta-chloroperbenzoic acid. After the crude product is filtered by a Millipore spray filter and the residue is subsequently purified by means of preparative HPLC (mobile solvent: acetonitrile/water gradient), 82 mg (83% of theory) of the title compound is obtained.

Workup

  1. filtrationAfter the crude product is filtered by a Millipore spray
  2. filtrationfilter
  3. customthe residue is subsequently purified by means of preparative HPLC (mobile solvent: acetonitrile/water gradient), 82 mg (83% of theory) of the title compound
  4. customis obtained

Sources & evidence

ORD record
ord-a274ed8ae6b44f59af1b3e309b67203a
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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