Hydrochloric Acid → HCID 59770233, compound

Participants

Reaction Steps

Mix 6-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-pyrazin-2-ylamine (35 mg, 0.117 mmol), triethylamine (34 μL, 0.234 mmol), N,N-dimethylaminopyridine (2 mg, 0.018 mmol), and methanesulfonyl chloride (10 μL, 0.123 mmol) in CH2Cl2 (2 mL). Stir at room temperature overnight and add 150 μL triethylamine and 40 μL methanesulfonyl chloride. Stir at room temperature for 6 h and add 1.00N aqueous HCl (1 mL). Load mixture onto a Varian ChemElut CE1005 solid-phase extraction cartridge, then elute, collect, and concentrate 45 mL CH2Cl2. Dissolve crude product in THF (5 mL), add 1.0M tetrabutylammonium fluoride (0.30 mL), and heat to reflux for 1 h. Cool to room temperature and dilute with H2O and brine. Extract into ethyl acetate, dry (MgSO4) and concentrate organics. Chromatograph on silica gel (4 g), eluting with 20%→35% ethyl acetate/hexanes to afford 19 mg (43%) of the title compound as a white solid. MS (ES) 378 (M+H), 376 (M−H); HPLC shows 100% purity.

Provenance & Evidence