Hydrochloric Acid → HCID 68323736, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 4-[3-(4-{[(3-chlorophenyl)sulfonyl]amino}-2,6-dimethylthieno[2,3-b]pyridin-3-yl)phenyl]-1-piperazinecarboxylate (60 mg, 0.098 mmol) (Example 31) in DCM (2 mL) was added 4M HCl in dioxane (0.122 mL, 0.489 mmol) and the mixture stirred for 3 h. Additional 4M HCl in dioxane (2.446 mL, 9.78 mmol) was then added and the mixture stirred overnight. Aqueous NaOH (5M) was then added to the solution dropwise until it was basic. Ethyl acetate (10 mL) was added and the mixture washed with water (2×5 mL). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by MDAP (acidic conditions) and further purification using HPLC (CHIRALPAK AD (250×20 mm-10 micron); isohexane/ethanol gradient, 18 mL/min) afforded the title compound (12.7 mg). LCMS (A) m/z: 513 [M+1]+, Rt 0.93 min (basic), Rt 1.01 min (acidic).

Provenance & Evidence