Pyridine → N-(7-hydroxy-4,5-dihydronaphtho[1,2-d]thiazol-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To 7-methoxy-4,5-dihydronaphtho[1,2-d]thiazol-2-amine (17 mg, 0.073 mmol) in dichloroethane (2 mL) and pyridine (17.37 mg, 0.220 mmol) was added benzoyl chloride (0.015 mL, 0.132 mmol) at room temperature. The reaction mixture was heated to 45° C. and stirred for 2 hours. The reaction mixture was cooled to room temperature, 3 ml of dichloromethane was added, and the contents were washed with sat. NaHCO3. The organic layer was dried over Na2SO4 and concentrated and dried under vacuum overnight. The residue was dissolved into 2 ml dichloromethane, cooled to 0° C. using an ice bath. Borontribromide (0.293 mL, 0.293 mmol) was added slowly at 0° C. The reaction mixture was allowed to warm to room temperature slowly and stirred at room temperature for 4 hours. The reaction mixture was quenched with a few drops of MeOH and purified on prep. HPLC (Luna 5 u C18 21.2*100 mm column; 0%-100% 10mins gradient; Solvent A: 10% MeOH-90% H2O-0.1% TFA; Solvent B: 90% MeOH-90% H2O-0.1% TFA). The desired fractions were collected, concentrated and dried overnight to provide 3.5 mg of product. (two-step yield: 11%). LC/MS M+1=323.1. The product had an HPLC retention time=3.31 min. (condition A). 1H NMR (400 MHz, CD3OD) δ ppm 7.99-8.07 (2H, m), 7.63 (2H, d, J=7.48 Hz), 7.57 (2H, d, J=7.70 Hz), 6.70 (2H, s), 2.98 (4H, d, J=4.84 Hz).

Provenance & Evidence