3-(2-Chlorobenzyl)pyrrolidine oxalate → 4-{[3-(2-Chlorobenzyl)pyrrolidin-1-yl]carbonyl}-5-(4-methylphenyl)isoxazole

HRID 1446217Notes

Reaction equation

HRID 1446217 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][CH:32]=[CH:31][C:24]=1[CH2:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1>>[Cl:22][C:23]1[CH:34]=[CH:33][CH:32]=[CH:31][C:24]=1[CH2:25][CH:26]1[CH2:30][CH2:29][N:28]([C:13]([C:9]2[CH:10]=[N:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[O:15])[CH2:27]1

Participants

3

Reactant 2

HCID 27353733-(2-Chlorobenzyl)pyrrolidine oxalateHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acid

Product 1

HCID 591700914-{[3-(2-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-(2-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 (6.4 mg). Calcd for C22H21ClN2O2: 380.1292, found 380.1300.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-848f421e6c8c42fb8f8b7e1ede75cf2f
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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