N,N'-Dimethylethylenediamine → 4-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

Participants

Reaction Conditions

Reaction Steps

In a 2-mL screw cap vial was introduced 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 23.9) (100 mg, 0.348 mmol), 5-iodo-1,3-dimethylpyridin-2(1H)-one (Step 23.2) (104 mg, 0.417 mmol), tripotassium phosphate (148 mg, 0.695 mmol), copper(I) iodide (6.62 mg, 0.035 mmol), N,N′-dimethylethylenediamine (7.48 μL, 0.070 mmol) and dioxane (2 mL). The reaction mixture was stirred for 6 hr at 120° C., concentrated, diluted with water, and extracted with EtOAc. The combined organic layers were washed once with water, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-3%) followed by crystallization of the resulting residue in Et2O to provide the title product (85 mg, 0.208 mmol, 69% yield) as a white solid. tR: 4.22 min (HPLC 1); tR: 0.96 min (LC-MS 2); ESI-MS: 409 [M+H]+ (LC-MS 2); Rf=0.42 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.15 (m, 2H) 1.18-1.33 (m, 2H) 1.86-2.01 (m, 6H) 3.39 (br. s., 3H) 3.75-3.90 (m, 1H) 6.08 (br. s., 1H) 7.30 (d, J=8.2 Hz, 2H) 7.36-7.47 (m, 3H) 7.75 (br. s., 1H).

Provenance & Evidence