Thiophenol → HCID 89389236, compound

Participants

Reaction Steps

To a solution of 1-{[cyclopropylmethyl-(4-oxo-3,4a,5,7,8,8a-hexahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-carbamoyl]-methyl}-piperidine-4-carboxylic acid (0.5 g, 1.24 mmol, 1 eq.) in 5 mL of DMF was added DIEA (0.432 mL, 2.47 mmol, 2 eq.), thiophenol (0.14 mL, 1.36 mmol, 1.1 eq.), followed by HATU (0.517 g, 1.36 mmol, 1.1 eq.) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred overnight. After 18 h, the reaction mixture was concentrated in vacuo to give an oil. This oil was purified by silica gel column chromatography (98/1/1 to 95/4/1 dichloromethane/MeOH/NH4OH) to give the title compound as an orange sticky oil (0.4 g). 1H NMR (400 MHz, chloroform-d) δ ppm 7.48-7.58 (m, 2H), 7.33-7.48 (m, 3H), 4.54-4.64 (m, 2H), 4.48-4.54 (m, 1H), 4.34-4.46 (m, 1H), 3.91-4.06 (m, 2H), 3.23-3.42 (m, 3H), 2.92-3.08 (m, 1H), 2.80-2.89 (m, 1H), 2.54-2.76 (m, 2H), 2.18-2.37 (m, 2H), 1.60-1.84 (m, 6H), 0.92-1.01 (m, 1H), 0.41-0.63 (m, 2H), 0.19-0.35 (m, 2H). Exact mass calculated for C26H33N4O4S1 497.2. MS (ESI) m/z 497.2 (M+H)+ (5-95% CH3CN/H2O over 2 min with 0.1% formic acid, Inertsil 3×3 mm C-8-3 column with flow rate of 2 mL/min).

Provenance & Evidence