Potassium Hydroxide → HCID 70978379, compound

Participants

Reaction Steps

To a solution of methyl 1-hydroxy-1-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-2,3-dihydro-1H-indene-5-carboxylate (900 mg, 1.709 mmol) in THF (8.6 mL) was added aqueous potassium hydroxide (1.82 mL, 17.09 mmol) and the mixture was stirred at rt overnight. The reaction was diluted with MeOH (10 mL) and water (10 mL) and the organic solvents were removed under reduced pressure. The pH was adjusted to ˜3 by addition of 1 M HCl, during which time the product precipitated. Collection of the precipitate by filtration furnished racemic 1-hydroxy-1-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-2,3-dihydro-1H-indene-5-carboxylic acid (749 mg, 85%) as a white solid. The racemic mixture was resolved by chiral SFC using a Chiral Technologies IA-H 3.0×25 cm, 5 uM column and a solvent system of 50% MeOH/CO2, running at 70 mL/min. Under these conditions, the two enantiomers eluted at 5.5 min and 10.5 min.

Provenance & Evidence