Sulfuric acid magnesium salt (1:1) → HCID 44380222, compound

Participants

Reaction Steps

To a solution of (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2methylpropan-1-one (120 mg in 8 mL dry chloroform) at 0° C. was added 194 mg magnesium sulfate followed by 51 mg 3-pyrido[2,3-b]pyrazin-7-yl-propionaldehyde and the mixture stirred at low temperature. After 1 hour, a solution of sodium cyanoborohydride (34 mg in 0.7 mL methanol) was added followed by 0.25 mL of a solution of acetic acid in methanol (1:9) and the reaction allowed to warm to room temperature. After 1 hour, the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion was washed with saturated aqueous sodium bicarbonate and then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate; then methylene chloride:methanol:ammonium hydroxide, 94:5:1) gave the title compound (12 mg).

Provenance & Evidence