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ChemicalBook CAS DataBase List 5-(TRIFLUOROMETHYL)-2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-OXAZOLE-4-CARBOXYLICACID

5-(TRIFLUOROMETHYL)-2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-OXAZOLE-4-CARBOXYLICACID synthesis

2synthesis methods
-

Yield:1083418-59-0 45%

Reaction Conditions:

Stage #1: 5-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxylic acidwith dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane; for 0.166667 h;
Stage #2: 3-(2-amino-4-chlorophenyl)-4H-[1,2,4]oxadiazol-5-one in dichloromethane at 20;

Steps:



δ-Trifluoromethyl^-^-trifluoromethyl-phenylj-oxazole^-carboxylic acid [5-chloro-2-(5- oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide (16)To a suspension of 5-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]-1 ,3- oxazole-4-carboxylic acid (0.25 g, 1 eq) in DCM (15 ml), EDC HCI (0.295 g, 2 eq) and DMAP (0.282 g, 3 eq) are added. The resulting solution is stirred for 10 min and 3-(2- amino-4-chloro-phenyl)-4H-[1 ,2,4]oxadiazol-5-one (0.166 g, 1 eq) (prepared as described by Valgeirsson et al. in Journal of Medicinal Chemistry 2004 47 (27) 6948- 6957) is added. The solution is stirred at room temperature overnight, diluted with DCM (20 ml), washed with 1.5 N HCI (30 ml) and water (30 ml), dried and evaporated to dryness, to give a pure white solid (0.176 g, 45% yield). LC-ESI-HRMS of [M-H]- shows 517,0135 Da. CaIc. 517,013827 Da, dev. -0,6 ppm.

References:

WO2008/138917,2008,A1 Location in patent:Page/Page column 30

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