5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide → 5-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

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Reaction Steps

5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (250 mg, 0.5 mmol) was dissolved in a mixture of THF (4 mL), AcOH (8 mL) and H2O (0.5 mL), heated at reflux for 16 h, then concentrated to dryness. The residue was dissolved in EtOAc, washed with sat aq NaHCO3, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by MPLC eluting with CH2Cl2/MeOH (0-5% gradient) to give 5-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (200 mg, 87% yield).

Provenance & Evidence