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

HRID 1446251Notes

Reaction equation

HRID 1446251 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.[F:25][C:26]([F:39])([F:38])[C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)=[CH:29][CH:28]=1>>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([N:35]2[CH2:36][CH2:37][CH:33]([C:30]3[CH:31]=[CH:32][C:27]([C:26]([F:25])([F:38])[F:39])=[CH:28][CH:29]=3)[CH2:34]2)=[O:16])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 459259353-[4-(Trifluoromethyl)phenyl]pyrrolidine oxalateHCID 686829214-Isoxazolecarboxylic acid, 5-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 591700995-[4-(Trifluoromethyl)phenyl]-4-({3-[4-(trifluoromethyl)phenyl]pyrrolidin-1-yl}carbonyl)isoxazole

Procedure

The title compound was prepared from 5-(4-trifluoromethylphenyl)isoxazole-4-carboxylic acid (12.9 mg, 0.050 mmol) and 3-[4-(trifluoromethyl)phenyl]pyrrolidine oxalate (18.3 mg, 0.060 mmol) as described in synthetic method C and thereafter purified by preparative HPLC method B to give a solid (5.5 mg). Calcd for C22H16F6N2O2: 454.1116, found 454.1116.

Workup

  1. custompurified by preparative HPLC method B

Sources & evidence

ORD record
ord-6e317e6bf7054af48f9b13fdaf344b80
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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