Boron tribromide → 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-(hydroxymethyl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

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Reaction Steps

BBr3 (1 M in CH2Cl2, 0.337 mL, 0.337 mmol) was added to a solution of 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (130 mg, 0.281 mmol) (Example 130) in CH2Cl2 (5 mL), under an argon atmosphere. The reaction mixture was stirred for 1 h at rt, quenched with brine (100 mL), and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (100 mL), dried on Na2SO4 and the solvent was evaporated off under reduced pressure. After purification by silica gel column chromatography (CH2Cl2/MeOH 2-8%), the resulting residue was triturated in diethyl ether to provide the title compound (28 mg) as a colorless solid. tR: 0.77 min (LC-MS 2); ESI-MS: 449.1 [M+H]+ (LC-MS 2); Rf=0.29 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.09 (m, 2H) 1.19-1.28 (m, 2H) 2.42 (s, 3H) 2.61 (s, 3H) 3.80-3.90 (m, 1H) 4.06 (dd, J=12.90, 5.87 Hz, 1H) 4.30 (dd, J=12.90, 4.30 Hz, 1H) 5.10 (dd, J=5.87, 4.30 Hz, 1H) 6.46 (s, 1H) 7.26-7.41 (m, 5H) 8.49 (s, 1H).

Provenance & Evidence