Hydrochloric Acid → HCID 71280824, compound

Participants

Reaction Steps

N-(2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide was synthesized from 1-(2-(4-fluorophenyl)oxazol-4-yl)-N1,N1-dimethylethane-1,2-diamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6. The free base was then stirred with HCl in dioxane solution (4 mL) for 0.5 h at 0° C. to room temperature. The reaction mixture was concentrated and triturated with diethyl ether to afford N-(2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide hydrochloride (130 mg, yield 16%) as light brown solid. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (br s, 1H), 9.18-9.15 (t, J=5.6 Hz, 1H), 8.55-8.54 (m, 2H), 8.27-8.25 (m, 1H), 8.21-8.19 (m, 1H), 8.11-8.07 (m, 2H), 7.79-7.75 (t, J=7.8 Hz, 1H), 7.45-7.41 (t, J=8.9 Hz, 2H), 4.84-4.81 (t, J=6.1 Hz, 1H), 4.20-4.13 (m, 1H), 3.87-3.82 (m, 1H), 2.87-2.84 (dd, J=6.9 Hz, 5.0 Hz, 6H). MS (ESI) m/z: Calculated for C23H19F4N5O3: 489.14. found: 490.2 (M+H)+.

Provenance & Evidence