Sodium Hydroxide → 4-Ethyl-1-(3-{2-[(ethylcarbamoyl)amino]-7-(pyridin-2-yl)-1,3-benzothiazol-5-yl}-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylic acid

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Reaction Steps

Ethyl 4-ethyl-1-(3-{2-[(ethylcarbamoyl)amino]-7-(pyridin-2-yl)-1,3-benzothiazol-5-yl}-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylate (70 mg, 0.09 mmol) was dissolved in EtOH (15 mL) and 2M aqueous NaOH (5 mL) and stirred at 90° C. for 18 h. The reaction was cooled to rt and concentrated to ˜⅕ volume. Water (10 mL) and DCM (10 mL) were added and the aqueous layer separated, the organic layer discarded and the aqueous layer acidified to pH˜2 and extracted with DCM (3×10 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo to give a brown solid, which was purified by flash column chromatography (Biotage, SP4, 12 g, 2-8% MeOH, DCM) to afford Compound 232 as a cream solid (18 mg, 38%).

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