Sodium hydride → HCID 57771773, compound

Participants

Reaction Steps

Place 1-methyl-piperidin-3-ol in DCM (10 mL). Add diisopropylethylamine (DIEA) (1.84 mL, 11.15 mmol) followed by methanesulfonyl chloride (0.866 mL, 11.15 mmol). Stir at rt for 17 h. Add DCM (10 mL) and wash the organic layer with 1N NaOH (20 mL). Collect the organic layer, dry over MgSO4, filter, and concentrate in vacuo. Place methyl-(5-nitro-benzooxazol-2-yl)-amine (600 m g, 3.11 mmol) in DMF (10 mL). Add 60% NaH in mineral oil (124 mg, 3.11 mmol) and stir for 10 min. Then add methanesulfonic acid 1-methyl-piperidin-3-yl ester (1.80 g, 9.30 mmol) dissolved in DMF (5 mL). Heat the reaction to 80° C. for 19 h. Cool to rt and add ethyl acetate (50 mL) and water (50 mL). Separate the organic layer and wash with water (2×25 mL), then brine (25 mL). Collect the organic layer, dry over MgSO4, filter, and concentrate in vacuo. Chromatograph (silica gel, eluting with 0-10% 2M NH3 in MeOH:DCM, then 10% 2M NH3 in MeOH:DCM) to yield 445 mg (49%) of the title compound: mass spectrum (ion-spray): (m/z)=291.3 (M+1).

Provenance & Evidence