Triethylamine → HCID 89579668, compound

Participants

Reaction Steps

4-[3-(2-aminoethoxymethyl)-8-azabicyclo[3.2.1]octan-8-yl]-N-isopropyl-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide (0.1 g, 0.2 mmol) and was stirred in DCM (10 mL) at 0° C. Triethylamine (0.04 g, 0.06 mL, 0.4 mmol) was added followed by methanesulfonyl chloride (0.04 g, 0.02 mL, 0.3 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The solvent was removed at reduced pressure. The resulting residue was taken up in DCM, washed with water, dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by acidic prep HPLC (method 1). Desired fractions were combined and concentrated at reduced pressure. The residue was taken up in DCM, washed with sat. NaHCO3 solution, the organic dried over Na2SO4 and concentrated at reduced pressure to afford N-isopropyl-4-[3-[2-(methanesulfonamido)ethoxymethyl]-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide (41 mg).

Provenance & Evidence