Sodium Hydroxide → HCID 25029778, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-fluoro-4-iodo-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (124 mg, 0.28 mmol), 1N aqueous NaOH solution (0.30 ml, 0.30 mmol) and ethanol (4 ml) was heated at 65° C. for 45 minutes. The reaction mixture was concentrated in vacuo then the resultant residue was azeotroped with toluene (2×2 ml) to give a solid residue. The solid residue was dissolved in anhydrous THF (4 ml) before O-(2-vinyloxy-ethyl)-hydroxylamine (58 mg, 0.56 mmol), EDCI (67 mg, 0.35 mmol), HOBt (53 mg, 0.39 mmol) and DIPEA (147 μl, 0.84 mmol) were added. After stirring for 18 hours at ambient temperature the solvent was evaporated and the resultant residue was diluted with water (20 ml), then extracted with ethyl acetate (30 ml) followed by dichloromethane (30 ml). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a yellow oil. The resultant yellow oil was purified by flash chromatography (Si-SPE, dichloromethane:methanol, gradient 100:0 to 98:2) to afford the title compound as a yellow solid (91 mg, 65%). LCMS (method B): RT=3.05 min, M+H+=500.

Provenance & Evidence