7-Fluoro-3-(2-fluoro-4-iodo-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide → 7-Fluoro-3-(2-fluoro-4-iodo-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-hydroxy-ethoxy)-amide

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Reaction Steps

A solution of 7-fluoro-3-(2-fluoro-4-iodo-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide (100 mg, 0.19 mmol) in a mixture of methanol and DCM was loaded onto a 5 g SCX-2 cartridge, which was eluted with methanol followed by a 2M solution of ammonia in methanol. Appropriate fractions were combined and concentrated under reduced pressure. The residual solid was purified by column chromatography (Si-SPE, gradient 0-40% tert-butyl dimethyl ether in DCM then 10% methanol in DCM) to afford the title compound as a yellow solid (50 mg, 53%). LCMS (method A): RT=9.60 min, M+H+=492. 1H NMR (CD3OD, 400 MHz) 3.58 (2H, t, J=4.89 Hz), 3.84 (2H, t, J=4.91 Hz), 6.89 (1H, t, J=8.76 Hz), 6.98 (1H, dd, J=8.41, 2.15 Hz), 7.21-7.26 (1H, m), 8.02 (1H, d, J=5.61 Hz), 8.45 (1H, dd, J=8.25, 5.61 Hz), 8.53-8.59 (1H, m).

Provenance & Evidence