1-Chloro-N,N-2-trimethylpropenylamine → 4-(4-Chlorophenyl)-5-(1,6-dihydro-1-methyl-6-oxo-3-pyridinyl)-4,5-dihydro-2-[(4-methoxyphenyl)methyl]-3-methylpyrrolo[3,4-c]pyrazol-6(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid (Step 1.5) (125 mg, 0.254 mmol) in CH2Cl2 (2 mL) under Ar was added 1-chloro-N,N,2-trimethyl-1-propenylamine (0.047 mL, 0.355 mmol) at 0° C. The reaction mixture was stirred for 1 hr at 0° C., quenched with a saturated aqueous solution of NaHCO3 (75 mL), and extracted with CH2Cl2. The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL), dried over Na2SO4 the solvent was and evaporated off under reduced pressure. The crude residue was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-3.5%) to afford the title product (92 mg, 0.194 mmol, 76% yield) as a greenish solid. tR: 4.32 min (HPLC 1); tR: 0.97 min (LC-MS 2); ESI-MS: 475 [M+H]+ (LC-MS 2); Rf=0.65 (CH2Cl2/MeOH 9:1).

Provenance & Evidence