3-Hydrazinyl-2-methoxypyridine → 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Participants

Reaction Steps

The title compound was prepared in analogy to the procedure described in Example 57 using 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 90.1) and 3-hydrazinyl-2-methoxypyridine (Step 71.1). The crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2) followed by preparative achiral SFC (column Propyl-pyridyl-urea, gradient 12-17% in 6 min_total 11 min) and triturated in Et2O. tR: 0.99 min (LC-MS 2); ESI-MS: 500 [M+H]+ (LC-MS 2); Rf=0.33 (1% ammonia/5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.07 (s, 3H) 2.45 (s, 3H) 2.62 (s, 3H) 3.92 (s, 3H) 6.59 (s, 1H) 7.21 (dd, J=7.6, 5.01 Hz, 1H) 7.34 (s, 1H) 7.37-7.48 (m, 4H) 8.00 (dd, J=7.6, 1.71 Hz, 1H) 8.33 (dd, J=4.9, 1.6 Hz, 1H) 8.47 (s, 1H).

Provenance & Evidence