Triethylamine → HCID 117702799, compound

Participants

Reaction Steps

To a stirred solution of ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylate (Step 23.5) (2.12 g, 6.33 mmol) and triethylamine (4.41 mL, 31.7 mmol) in CH2Cl2 (4 mL) under Ar was added Ms2O (2.206 g, 12.66 mmol) at −10° C. The reaction mixture was stirred for 30 min at this temperature. 4-Methoxybenzylamine (0.827 ml, 6.33 mmol) was added at 30° C. After 15 h at rt, the reaction mixture was quenched with a saturated aqueous solution of NaHCO3 (100 mL), and extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL), dried (Na2SO4) and evaporated. The crude material was purified by silica gel column chromatography (Hex/EtOAc 5-20%) to afford the title product (2.22 g, 4.89 mmol, 77% yield) as a colorless oil. tR: 1.12 min (LC-MS 2); ESI-MS: 454 [M+H]+ (LC-MS 2); Rf=0.85 (hexane/EtOAc 1:1).

Provenance & Evidence