Ammonium Chloride → HCID 131729412, compound

Participants

Reaction Conditions

Reaction Steps

Add sodium cyanoborohydride (0.044 g, 0.703 mmol) to a mixture of 2-(4-chloro-phenyl)-6-[6-(pyrrolidin-3(R)-yloxy)-pyridin-3-yl]-6H-thieno[2,3-c]pyridin-7-one (0.0745 g, 0.176 mmol) and (1-ethoxy-cyclopropoxy)-trimethyl-silane (0.14 mL, 0.703 mmol) in acetic acid (0.05 mL) and methanol (10 mL) at room temperature. Reflux the mixture overnight at 80° C. Dilute the reaction mixture with dichloromethane and wash with 1.0M NaOH. Dilute the organic phase with methanol, dry over sodium sulfate, filter, and concentrate. Purify the mixture using silica gel flash column chromatography, eluting with 2-12% MeOH (2N NH3)/CH2Cl2. Triturate the residue with methanol to yield a white solid. Dissolve the white solid in dichloromethane/methanol, then add ammonium chloride (2 mg) and sonicate the resulting mixture until dissolution of the ammonium chloride. Concentrate the solution, then pump on high vacuum overnight to yield the desired product (0.020 g, 23%). MS/ES m/z (35Cl) 464.2 [M+H+].

Provenance & Evidence