Ammonia → HCID 68549497, compound

Participants

Reaction Conditions

Reaction Steps

Preparation of 345-(2,5-difluorophenyl)-3-((S)-2-methoxypropanoyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propanimidamide hydrochloride: To a cooled (0° C.) solution of 3-(5-(2,5-difluorophenyl)-3-((S)-2-methoxypropanoyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propanenitrile (0.053 g, 0.13 mmol) in ethanol (0.5 mL) was added a 9.8 M solution of ethanolic HCl (0.5 mL). After stirring at 0° C. for 10 minutes and then at room temperature for 4 hours, the reaction mixture was concentrated under reduced pressure. To the residue was added NH3 (1.0 mL, 7.0 mmol, 7 M solution in methanol). After stirring at room temperature for 30 minutes, the mixture was concentrated under reduced pressure. The residue was chromatographed (dichloromethane followed by 20% MeOH and 1% aqueous NH4OH in dichloromethane) to afford the product as a mixture of diastereomers (3.4 mg, 15% yield). MS ESI (+) m/z 433 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 9.0 (br, 4H), 8.7 (br, 4H), 7.51 (m, 2H), 7.38 (m, 8H), 7.32 (m, 2H), 7.14 (m, 4H), 4.73 (m, 2H), 3.57 (m, 2H), 3.42 (s, 3H), 3.35 (s, 3H), 2.75 (m, 4H), 2.33 (m, 1H), 2.23 (m, 1H), 1.52 (d, 3H, J=6.3 Hz), 1.48 (d, 3H, J=7.0 Hz).

Provenance & Evidence