3-(4-METHYLPHENYL)PYRROLIDINE OXALATE → 4-{[3-(4-Methylphenyl)pyrrolidin-1-yl]carbonyl}-5-[4-(trifluoromethyl)phenyl]isoxazole

HRID 1446250Notes

Reaction equation

HRID 1446250 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([OH:16])=O)=[CH:5][CH:4]=1.C(O)(=O)C(O)=O.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:36][CH2:35][NH:34][CH2:33]2)=[CH:28][CH:27]=1>>[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([CH:32]2[CH2:36][CH2:35][N:34]([C:14]([C:10]3[CH:11]=[N:12][O:13][C:9]=3[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:17])=[CH:8][CH:7]=3)=[O:16])[CH2:33]2)=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 177497503-(4-METHYLPHENYL)PYRROLIDINE OXALATEHCID 686829214-Isoxazolecarboxylic acid, 5-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 591701374-{[3-(4-Methylphenyl)pyrrolidin-1-yl]carbonyl}-5-[4-(trifluoromethyl)phenyl]isoxazole

Procedure

The title compound was prepared from 5-(4-trifluoromethylphenyl)isoxazole-4-carboxylic acid (12.9 mg, 0.050 mmol) and 3-(4-methylphenyl)pyrrolidine oxalate (15.1 mg, 0.060 mmol) as described in synthetic method C and thereafter purified by preparative HPLC method B to give a solid (6.3 mg). Calcd for C22H19F3N2O2: 400.1399, found 400.1400.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-eddb79cdc86946ccba8b4cd3de469ef9
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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