3-(4-Methylbenzyl)pyrrolidine hydrochloride → 5-(2-Chlorophenyl)-4-{[3-(4-methylbenzyl)pyrrolidin-1-yl]carbonyl}isoxazole

HRID 1446234Notes

Reaction equation

HRID 1446234 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[CH:10][C:9]=1[C:13]([OH:15])=O.Cl.[CH3:17][C:18]1[CH:29]=[CH:28][C:21]([CH2:22][CH:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)=[CH:20][CH:19]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[CH:10][C:9]=1[C:13]([N:25]1[CH2:26][CH2:27][CH:23]([CH2:22][C:21]2[CH:20]=[CH:19][C:18]([CH3:17])=[CH:29][CH:28]=2)[CH2:24]1)=[O:15]

Participants

3

Reactant 2

HCID 177497553-(4-Methylbenzyl)pyrrolidine hydrochlorideHCID 224942765-(2-Chlorophenyl)-1,2-oxazole-4-carboxylic acid

Product 1

HCID 591701105-(2-Chlorophenyl)-4-{[3-(4-methylbenzyl)pyrrolidin-1-yl]carbonyl}isoxazole

Procedure

The title compound was prepared from 5-(2-chlorophenyl)isoxazole-4-carboxylic acid (11.2 mg, 0.050 mmol) and 3-(4-methylbenzyl)pyrrolidine hydrochloride (12.7 mg, 0.060 mmol) as described in synthetic method C and thereafter purified by preparative HPLC method B to give a solid (8.4 mg). Calcd for C22H21N2O2: 380.1292, found 380.1296.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-00af55f296d64b0a8b04ed0114527480
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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