Triethylamine → ethyl 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylate

Participants

Reaction Steps

To a stirred solution of Ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylate (Step 1.3) (423 mg, 1.020 mmol) and triethylamine (1.42 mL, 10.20 mmol) in CH2Cl2 under Ar was added Ms2O (355 mg, 2.039 mmol) at −10° C. The reaction mixture was stirred for 30 min at this temperature. 5-Amino-1-methyl-2(1H)-pyridinone oxalate salt (218 mg, 1.020 mmol) was added at 30° C. After 1 hr, the reaction mixture was quenched with a saturated aq. NaHCO solution, and extracted with CH2Cl2. The combined organic layers were washed a saturated aqueous solution of NaHCO3, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-2%) to afford the title product (147 mg, 0.282 mmol, 28% yield) as a greenish solid. tR: 4.68 min (HPLC 1); tR: 1.06 min (LC-MS 2); ESI-MS: 521 [M+H]+ (LC-MS 2); Rf=0.56 (CH2Cl2/MeOH 9:1).

Provenance & Evidence