Diisopropylethylamine → HCID 178496746, compound

Participants

Reaction Steps

Preparation of N′-cyano-N-(2-(5-(2,5-difluorophenyl)-3-((S-2-methoxypropanoyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl)acetamidine: To a solution of ethyl N-cyanoacetimidate (0.025 g, 0.22 mmol) and (2S)—(2-(2-aminoethyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one hydrochloride (0.018 g, 0.038 mmol) in EtOH (0.3 mL) was added diisopropylethylamine (0.033 mL, 0.19 mmol). After stirring at room temperature for 14 hours, the mixture was diluted with 10% Na2CO3 (30 mL) and extracted with dichloromethane. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed (3% MeOH in dichloromethane) to provide the product as a mixture of diastereomers (13.0 mg, 73% yield). MS ESI (+) m/z 472 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.51 (m, 2H), 7.37 (m, 6H), 7.33 (m, 4H), 7.16 (m, 4H), 6.93 (br. t, 1H, J=4.7 Hz), 6.73 (br. t, 1H, J=4.7 Hz), 4.73 (m, 2H), 4.00 (m, 2H), 3.45-3.29 (m, 9H), 3.21 (m, 1H), 2.82 (m, 1H), 2.75 (m, 1H), 2.16 (s, 3H), 2.15 (s, 3H), 1.46 (d, 3H, J=6.3 Hz), 1.43 (d, 3H, J=7.0 Hz).

Provenance & Evidence