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0 °C

A suspension of 2-chloro-4-[[[[1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]methyl]amino]carbonyl]benzoic acid, methyl ester (87.8 mg, 0.206 mmol) in methanol (1 mL) was cooled to ˜0° C. and 1 M sodium hydroxide (0.206 mL, 0.206 mmol) was added. The cooling bath was removed and the reaction mixture was allowed to stir overnight. A further portion of sodium hydroxide (1 M; 0.2 mL, 0.2 mmol) was added and the mixture was stirred at room temperature for 7 h. The solvent was evaporated and the residue was dissolved in water (25 mL) and washed with ethyl acetate (2×10 mL). The aqueous layer was made acidic with 1 M HCl and extracted with ethyl acetate (2×20 mL). These extracts were combined, washed with brine (10 mL), dried (MgSO4), filtered, and concentrated to give 2-chloro-4-[[[[1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]methyl]amino]carbonyl]benzoic acid (77.3 mg, 91%) as a white solid.

1. customThe cooling bath was removed
2. stirringthe mixture was stirred at room temperature for 7 h
3. customThe solvent was evaporated
4. dissolutionthe residue was dissolved in water (25 mL)
5. washwashed with ethyl acetate (2×10 mL)
6. extractionextracted with ethyl acetate (2×20 mL)
7. washwashed with brine (10 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated