Hydrochloric Acid → HCID 11691851, compound

Participants

Reaction Conditions

Reaction Steps

To 25 mg (0.05 mmol) of 4-{5-methyl-4-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxymethyl]-oxazol-2-yl}-benzoic acid (example 81) in 1.5 ml of CH2Cl2 were added 8.6 mg (0.11 mol) of dimethylamine.HCl and 23 μl (0.11 mmol) of NMM. The solution was cooled to 0° C. and 13.1 mg (0.07 mmol, 1.3 eq) of EDCI and 1.4 mg (0.01 mmol) of HOBT were added. The mixture was stirred at room temperature overnight. Water was added and the inorganic phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated. Column chromatography with CH2Cl2/MeOH 98:2 gave 22 mg (83%) N,N-dimethyl-4-{5-methyl-4-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxymethyl]-oxazol-2-yl}-benzamide as a colorless oil, MS: 501 (M−H)−.

Provenance & Evidence