6-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine → 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]-triazolo[4,3-b]pyridazin-6-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 110 using 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 85.6) and 6-chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine (Step 111.2). The crude material was first purified by silica gel column chromatography (EtOAc/MeOH 0.5-1%), followed by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 9-14% in 6 min_total 11 min). tR; 4.66 min (HPLC 1); tR: 1.08 min (LC-MS 2); ESI-MS: 434 [M+H]+ (LC-MS 2); Rf=0.14 (EtOAc); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.04-1.08 (m, 2H) 1.21-1.26 (m, 2H) 1.90 (s, 3H) 2.51 (s, 3H) 2.57 (d, J=1.2 Hz, 3H) 3.82 (dt, J=7.4, 3.7 Hz, 1H) 6.45 (s, 1H) 7.32-7.37 (m, 2H) 7.42-7.47 (m, 2H) 8.08-8.14 (m, 1H).

Provenance & Evidence