Iodoethane → HCID 86292191, compound

Participants

Reaction Conditions

Reaction Steps

NaH (19.19 mg, 0.48 mmol) was added to a stirred solution of 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-hydroxy-2-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6-(2H)-one (Example 73) (142 mg, 0.369 mmol) in DMF (1 mL) at 0° C. and the reaction was stirred at 0° C. for 20 min. Iodoethane (0.036 mL, 0.443 mmol) was added and the resulting mixture was stirred at RT for 20 min. The reaction was diluted with EtOAc and water and both phases separated. The aq. layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (1% ammonia/7.5% MeOH/CH2Cl2) to afford, after trituration in Et2O, the title product (77 mg, 0.186 mmol, 50% yield) as white solid. tR: 0.91 min (LC-MS 2); ESI-MS: 413 [M+H]+ (LC-MS 2); Rf=0.39 (1% ammonia/7.5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=6.8 Hz, 3H) 1.91 (s, 3H) 3.35 (s, 3H) 3.60-3.77 (m, 4H) 3.89-4.03 (m, 1H) 6.20 (s, 1H) 7.25 (d, J=8.6 Hz, 2H) 7.30-7.44 (m, 3H) 7.66 (d, J=2.7 Hz, 1H).

Provenance & Evidence