Ethylene Glycol → 2-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzoic acid

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Reaction Steps

10% NaOH solution (25 mL) was added to N-{4-[6-amino-5-(2-cyano-benzyloxy)-pyridin-3-yl]-phenyl)methanesulfonamide (Example I-135, 650 mg, 1.65 mmol) in ethylene glycol (55 mL). The mixture was heated to reflux and allowed to stir for 24 hr. The reaction was cooled to room temperature. Most of the solvent was evaporated and the mixture was acidified. The precipitated solid was filtered out to afford 2-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzoic acid as light brown solid. The filtrate was neutralized and extracted with EtOAc (5×20 mL). The organic layer was combined, dried over MgSO4, and concentrated to yield 2-[2-Amino-5-(4-methanesulfonylamino-phenyl)-pyridin-3-yloxymethyl]-benzamide as an off-white solid.

Provenance & Evidence