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

HRID 1446255Notes

Reaction equation

HRID 1446255 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.[Cl:25][C:26]1[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=1[CH2:28][CH:29]1[CH2:33][CH2:32][NH:31][CH2:30]1>>[Cl:25][C:26]1[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=1[CH2:28][CH:29]1[CH2:33][CH2:32][N:31]([C:14]([C:10]2[CH:11]=[N:12][O:13][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:17])=[CH:8][CH:7]=2)=[O:16])[CH2:30]1

Participants

3

Reactant 2

HCID 27353733-(2-Chlorobenzyl)pyrrolidine oxalateHCID 686829214-Isoxazolecarboxylic acid, 5-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 591700224-{[3-(2-Chlorobenzyl)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-(2-chlorobenzyl)pyrrolidine oxalate (17.1 mg, 0.060 mmol) as described in synthetic method C and thereafter purified by preparative HPLC method B to give a solid (9.2 mg). Calcd for C22H18ClF3N2O2: 434.1009, found 434.1000.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-1b76dbef514b4eac97321403c187a8c7
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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