5-(p-Tolyl)isoxazole-4-carboxylic acid → 5-(4-Methylphenyl)-4-({3-[4-(trifluoromethyl)phenyl]pyrrolidin-1-yl}carbonyl)isoxazole

HRID 1446208Notes

Reaction equation

HRID 1446208 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([OH:15])=O)=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[F:22][C:23]([F:36])([F:35])[C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:34][CH2:33][NH:32][CH2:31]2)=[CH:26][CH:25]=1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:32]2[CH2:33][CH2:34][CH:30]([C:27]3[CH:28]=[CH:29][C:24]([C:23]([F:22])([F:35])[F:36])=[CH:25][CH:26]=3)[CH2:31]2)=[O:15])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acidHCID 459259353-[4-(Trifluoromethyl)phenyl]pyrrolidine oxalate

Product 1

HCID 591701045-(4-Methylphenyl)-4-({3-[4-(trifluoromethyl)phenyl]pyrrolidin-1-yl}carbonyl)isoxazole

Procedure

The title compound was prepared from 5-(4-methylphenyl)isoxazole-4-carboxylic acid (10.2 mg, 0.050 mmol) and 3-[4-(trifluoromethyl)phenyl]pyrrolidine oxalate (15.1 mg, 0.050 mmol) as described in synthetic method B and thereafter purified by preparative HPLC method B to give a solid (5.3 mg). Calcd for C22H19F3N2O2: 400.1399, found 400.1403.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-02be30ad51664c678f915ebddeebe1c8
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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