Acetic Anhydride → HCID 91826327, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 5-(8-amino-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 126.3) (40 mg, 0.092 mmol) and Ac2O (0.434 mL, 4.60 mmol) in pyridine (2 mL) under Ar and the resulting mixture was heated up and stirred for 20 hr at 115° C. The reaction was quenched with a saturated aq.NaHCO3 solution and extracted with EtOAc. The combined organic layers were washed with a saturated aq. NaHCO3 solution, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (CH2Cl2/MeOH 1-4%) and triturated in Et2O to afford the title product (27 mg, 0.057 mmol, 62% yield) as white solid. tR: 4.73 min (HPLC 1); tR: 1.07 min (LC-MS 2); ESI-MS: 477 [M+H]+ (LC-MS 2); ESI-MS: 475 [M−H]− (LC-MS 2); Rf=0.50 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.11 (m, 2H) 1.17-1.30 (m, 2H) 1.90 (s, 3H) 2.25 (s, 3H) 2.51 (s, 3H) 3.76-3.88 (m, 1H) 6.43 (s, 1H) 7.29-7.37 (m, 2H) 7.38-7.48 (m, 2H) 9.12 (s, 1H) 11.07 (s, 1H).

Provenance & Evidence