Hydrochloric Acid → HCID 70982683, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-(3-benzyl-1-oxoisoindolin-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (example 1.7, 111 mg, 0.26 mmol) in dry THF (1.6 mL) was added borane dimethyl sulfide complex (0.78 mL, 1.56 mmol, 2M in THF) under N2. The reaction mixture was heated up to 65° C. for 7 hours, then stirred at room temperature for overnight. Quenched reaction by carefully addition of 0.5 N HCl (0.5 mL) solution and the mixture was refluxed for 2 hours, then basified the reaction mixture with 1N NaOH aqueous to pH=8-9, extracted 2× with ethyl acetate, this was separated. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 5-10% MeOH in DCM (0.5% NEt3 added), 22.2 mg (21%) of the product was obtained.

Provenance & Evidence