Sodium Hydroxide → HCID 66778224, compound

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Reaction Steps

Ethyl 3-{[(4-{[{5-[(3-cyanopyridin-2-yl)oxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (234 mg) obtained in Example A197 was dissolved in ethanol (1.5 mL) and tetrahydrofuran (1.5 mL), 1N aqueous sodium hydroxide solution (0.78 mL) was added to the solution, and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure, water (4 mL) was added, and the mixture was neutralized with 1N hydrochloric acid (0.78 mL) under ice-cooling. The resulting precipitate was collected by filtration and dried. The obtained residue was purified by preparative HPLC “instrument: Gilson Inc., preparative HPLC system; column: Develosil ODS-UG-10, S-5 μm, 50×100 mm; solvent: SOLUTION A; 0.1% trifluoroacetic acid-containing water, SOLUTION B; 0.1% trifluoroacetic acid-containing acetonitrile, (SOLUTION A:SOLUTION B=95:5-0:100); flow rate: 150 mL/min; detection method: UV 220 nm”. To the fractionated fraction was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to give the title compound (73 mg, 33%) as a colorless amorphous form.

Provenance & Evidence