Boron tribromide → HCID 178484079, compound

Participants

Reaction Steps

To a suspension of trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-6-methoxy-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide (473 mg) obtained in Example 23 in dichloromethane (20 ml) is added dropwise boron tribromide (3.5 g) over 2 minutes at −78° C. The mixture is stirred at room temperature for 4 days, and the reaction solution is poured into ice-water, neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with a mixed solvent of ethyl acetate-tetrahydrofuran. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is suspended in chloroform/diethyl ether, and the precipitates are collected by filtration, and dried to give trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-6-hydroxy-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (335 mg). This product (48 mg) is suspended in methanol and treated with 4N hydrogen chloride in dioxane to give the title compound (54 mg).

Provenance & Evidence