Pyridine → HCID 89573556, compound

Participants

Reaction Conditions

Reaction Steps

DCM (40 mL) and pyridine (0.539 mL, 6.67 mmol) were added to rel-N-(((3S,4S)-7-fluoro-3-(hydroxymethyl)-4-methylchroman-4-yl)carbamothioyl)benzamide from step F4 (832 mg, 2.22 mmol), under an atmosphere of dry nitrogen. The mixture was cooled to −78° C. Triflic anhydride (0.751 mL, 4.44 mmol) was slowly added to the reaction solution over 10 min. The resulting mixture was stirred for 15 min and then further stirred for 1 h while warming to 0° C. After adding ethyl acetate, a saturated solution of sodium bicarbonate was added. The mixture was extracted with ethyl acetate, the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was dissolved in dichloromethane and one drop of water and one drop of TFA was added. The reaction was stirred for 15 min, then concentrated in vacuo to afford rel-N-((4aR,10bS)-8-fluoro-10b-methyl-4,4a,5,10b-tetrahydrochromeno[4,3-d][1,3]thiazin-2-yl)benzamide. The crude product was used for subsequent chemistry without further purification. LCMS (M+H)+=357.2.

Provenance & Evidence