Triethylamine → HCID 178496745, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-((S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one (Example 5, Steps A-F; 57.5 mg, 0.117 mmol) and methyl acetimidate hydrochloride (192 mg, 1.75 mmol) in methanol was added triethylamine (355 mg, 3.51 mmol). After heating at 50° C. for 16 hours, the mixture was concentrated under reduced pressure. The residue was chromatographed (15:85:1 MeOH/dichloromethane/NH4OH), and the isolated material %% as treated with excess HCl in MeOH then concentrated to afford the product. MS ESI (+) m/z 461 (M+1) detected. 1H NMR (400 MHz, CD3OD) δ 7.65-7.60 (m, 1H), 7.49-7.45 (m, 2H), 7.42-7.38 (m, 2H), 7.35-7.29 (m, 3H), 4.80 (q, 1H, J=7.1 Hz), 3.50-3.40 (m, 2H), 3.36 (s, 3H), 3.28-3.19 (m, 1H), 2.65-2.57 (m, 1H), 2.22 (s, 3H), 2.21-2.12 (m, 1H), 1.75-1.64 (m, 1H), 1.44 (d, 3H, J=7.1 Hz).

Provenance & Evidence