6-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine → 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

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Reaction Steps

The title product was prepared in analogy to the procedure described in Example 110 using 4-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 71.4) 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 (CH2Cl2/MeOH 1-5%), followed by preparative achiral SFC (column Propyl-pyridyl-urea, gradient 9-14% in 6 min_total 11 min). tR: 4.71 min (HPLC 1); tR: 1.10 min (LC-MS 2); ESI-MS: 501 [M+H]+ (LC-MS 2); Rf=0.44 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (s, 3H) 2.51-2.57 (m, 6H) 3.92 (s, 3H) 6.61 (s, 1H) 7.20 (dd, J=7.8, 5.1 Hz, 1H) 7.37-7.44 (m, 2H) 7.47-7.54 (m, 2H) 7.97-8.06 (m, 2H) 8.32 (d, J=4.3 Hz, 1H).

Provenance & Evidence