Sodium methanethiolate → HCID 178503677, compound

Participants

Reaction Conditions

Reaction Steps

3-[4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-(1-methylethenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-1,2,4-oxadiazol-5(4H)-one (synthesized in a manner similar to Example 9.1; 100 mg, 0.22 mmol) was taken up in MeOH (1.5 mL) at room temperature, and sodium thiomethoxide (376 mg, 5.4 mmol) was added. The reaction was sealed and heated at 65° C. for 2 hours. The reaction was then quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0 to 100% EtOAc/hexanes) to afford 3-{4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[1-methyl-2-(methylsulfanyl)ethyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (racemate). 1H NMR (300 MHz, CDCl3) δ 8.69-8.74 (m, 1H), 8.57-8.62 (m, 1H), 8.43 (s, 1H), 7.89-7.94 (m, 1H), 3.71-3.93 (m, 2H), 3.22-3.38 (m, 1H), 3.06-3.19 (m, 1H), 2.88-2.99 (m, 1H), 2.07 (s, 3H), 1.48-1.59 (m, 1H), 1.53 (d, J=6.7 Hz, 3H), 1.22-1.38 (m, 2H), 1.08-1.21 (m, 1H), 0.85-1.07 (m, 3H), 0.78 (d, J=6.4 Hz, 3H), 0.66-0.75 (m, 1H), 0.47-0.66 (m, 2H); MS ES calc'd. for C25H29ClN6O2S [M+H]+ 513. found 513.

Provenance & Evidence