Dichloromethane → HCID 67111738, compound

Participants

Reaction Conditions

Reaction Steps

A solution of CaCl2 (0.159 g, 1.43 mmol) in 1.00 ml of water was added to a solution of diethyl 2-acetamido-2-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methyl)malonate (0.330 g, 0.573 mmol) in THF (10.00 ml) and ethanol (10.00 ml). The reaction was cooled to 0° C. in ice bath before the addition of sodium borohydride (0.108 g, 2.87 mmol) was added and the solution became a yellow mixture. The reaction mixture was allowed to stir at ambient temperature for 2 h. DCM (5 ml) and additional sodium borohydride (0.108 g, 2.87 mmol) was added. After 18 h, the reaction was poured over DCM/1 N HCl, and the organic layer was washed with 1 N HCl, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, 40 g column, 0-15% MeOH/DCM to give N-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1,3-dihydroxypropan-2-yl)acetamide. MS (ESI) m/z: calculated: 491.2; Observed: 492.1 (M++1).

Provenance & Evidence