Triethylamine → HCID 12149142, compound

Participants

Reaction Steps

To a suspension of 2-hydroxymethyl-5-[5-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-pentyloxy]-4H-pyran-4-one EHT 5909 (0.10 g, 0.23 mmol) in 4 mL of dichloromethane at 5° C. were added triethylamine (35 μl, 0.25 mmol) and methanesulfonyl chloride (19.4 μl, 0.25 mmol). The reaction mixture was stirred 18 h at room temperature. Dichloromethane (20 mL) was added and the solution was washed with aqueous NaHCO3 10% (2×30 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by chromatography on silica using as eluent CH2Cl2:MeOH=98:2. After evaporation methanesulfonic acid 4-oxo-5-[6-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-hexyloxy]-4H-pyran-2-ylmethyl ester 9 (83 mg, 69%) was obtained as a white solid.

Provenance & Evidence