Trifluoroacetic acid → 4-(4-chlorophenyl)-3-methyl-5-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one

Participants

Reaction Conditions

Reaction Steps

In a 2-5 mL MW flask was introduced 4-(4-chlorophenyl)-2-(4-methoxybenzyl)-3-methyl-5-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-one (Example 1) (85 mg, 0.179 mmol) and TFA (1379 μL, 17.90 mmol). The reaction mixture was stirred for 30 min at 100° C. under MW irradiation, quenched with a saturated aq. NaHCO3 solution, and extracted with CH2Cl2. The combined organic layers were washed with a saturated aq. solution of NaHCO3, dried over Na2SO4, and evaporated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-8%) to afford the title compound (32 mg, 0.090 mmol, 50% yield) as a white solid. tR: 3.13 min (HPLC 1); tR: 0.69 min (LC-MS 2); ESI-MS: 355 [M+H]+ (LC-MS 2); Rf=0.40 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (s, 3H) 3.34 (s, 3H) 6.09 (s, 1H) 6.30 (d, J=9.4 Hz, 1H) 7.22 (d, J=8.2 Hz, 2H) 7.35 (d, J=8.6 Hz, 2H) 7.44 (dd, J=9.8, 2.74 Hz, 1H) 7.88 (d, J=3.1 Hz, 1H) 13.35 (br. s., 1H).

Provenance & Evidence