5-Chloro-3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridine → 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridin-5-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 102 using 5-chloro-3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridine (Step 109.4) and 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 85.6). The reaction mixture was quenched with a saturated aq. NaHCO3 solution (75 mL) and extracted with EtOAc. The combined organic layers were washed with a saturated aq. NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. The crude material was first purified by silica gel chromatography (hexane/EtOAc 25-45%). tR: 5.69 min (HPLC 1); tR: 1.26 min (LC-MS 2); ESI-MS: 434 [M+H]+ (LC-MS 2); Rf=0.58 (EtOAc/hexane 1:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.11 (m, 2H) 1.19-1.27 (m, 2H) 1.91 (s, 3H) 2.68 (s, 3H) 3.78-3.87 (m, 1H) 4.08 (s, 3H) 6.58 (s, 1H) 7.31 (d, J=8.6 Hz, 2H) 7.43 (d, J=8.2 Hz, 2H) 8.21 (s, 1H).

Provenance & Evidence