Hydrochloric Acid → HCID 90313826, compound

Participants

Reaction Steps

(S)-tert-Butyl 2-(3,5-difluorophenyl)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethylcarbamate (17A, 110 mg, 0.27 mmol) was dissolved in 2.7 mL of methanol and to it was added 0.7 mL of 4M HCl in 1,4-dioxane. The reaction mixture was allowed to stir at ambient temperature for 1 hour and the solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with methanol/methylene chloride to afford 90 mg of (S)-2-(3,5-difluorophenyl)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethanamine (0.26 mmol) which was dissolved in 5 mL of DMF and to it were added 2-(5-fluoro-1H-indol-3-yl)acetic acid (61 mg, 0.31 mmol) and N,N-diisopropylethylamine (0.226 mL, 1.3 mmol). The reaction mixture was cooled down to 0° C. and to it was added HATU (119 mg, 0.31 mmol). The reaction mixture was allowed to stir at ambient temperature for overnight and then purified by reverse phase HPLC eluting with acetonitrile/water (0.1% TFA) to afford the desired product. 1H NMR (400 MHz, DMSO) δ 10.93 (s, 1H), 8.79 (d, J=8.2 Hz, 1H), 7.94-7.73 (m, 2H), 7.56 (m, 3H), 7.27 (dd, J=8.7, 4.5 Hz, 1H), 7.12 (m, 2H), 7.00 (m, 3H), 6.84 (td, J=9.2, 2.5 Hz, 1H), 5.44 (m, 1H),), 3.52-3.12 (m, 4H). MS (m/z): 477.1 [M+H]+.

Provenance & Evidence