3-Furanol, tetrahydro- → HCID 86721273, compound

Participants

Reaction Conditions

Reaction Steps

To a mixed solution of 2-{2-[5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)acetamide (32.0 mg, 80 μmol) and 3-hydroxytetrahydrofuran (14 mg, 160 μmol) in THF (500 μL) and toluene (500 μL) were added DIAD (31.1 μL, 160 μmol) and triphenylphosphine (42.0 mg, 160 μmol), and the mixture was stirred at 80° C. for 14 hr. To the reaction mixture were added water and ethyl acetate, and the mixture was stirred for 10 min. The organic layer was filtered with a Top-Phase Separation Filter Tube. The filtrate was concentrated. The residue was purified by preparative HPLC to give a mixture (1:3, mol/mol) of a racemic title compound and racemic 2-{2-[3-(4-fluorophenyl)-1-(tetrahydrofuran-3-yl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)acetamide.

Provenance & Evidence