3-(4-Chlorobenzyl)pyrrolidine oxalate → 4-{[3-(4-Chlorobenzyl)pyrrolidin-1-yl]carbonyl}-5-(4-methylphenyl)isoxazole

HRID 1446213Notes

Reaction equation

HRID 1446213 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.[Cl:22][C:23]1[CH:34]=[CH:33][C:26]([CH2:27][CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:25][CH:24]=1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH:28]2[CH2:32][CH2:31][N:30]([C:13]([C:9]3[CH:10]=[N:11][O:12][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[O:15])[CH2:29]2)=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 177497533-(4-Chlorobenzyl)pyrrolidine oxalateHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acid

Product 1

HCID 591702004-{[3-(4-Chlorobenzyl)pyrrolidin-1-yl]carbonyl}-5-(4-methylphenyl)isoxazole

Procedure

The title compound was prepared from 5-(4-methylphenyl)isoxazole-4-carboxylic acid (10.2 mg, 0.050 mmol) and 3-(4-chlorobenzyl)pyrrolidine oxalate (17.1 mg, 0.060 mmol) as described in synthetic method B and thereafter purified by preparative HPLC method B to give a solid (8.1 mg). Calcd for C22H21ClN2O2: 380.1292, found 380.1295.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-77b99048b50b4986a5f18434512cf861
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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