Dimethylformamide dimethyl acetal → N'-[(4R)-3'-bromo-7'-(2-fluoro-3-pyridinyl)spiro[5,6-dihydro-1,3-oxazine-4,5'-chromeno[2,3-b]pyridine]-2-yl]-N,N-dimethylmethanimidamide

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Reaction Conditions

Reaction Steps

In a 25-mL flask, the (R)-3-bromo-7-(2-fluoropyridin-3-yl)-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazin]-2′-amine (0.350 g, 0.793 mmol) was suspended in 1,1-dimethoxy-N,N-dimethylmethanamine (5.29 mL, 39.7 mmol). The reaction mixture was heated to 100° C. for 1 h. The reaction was concentrated, and the residue was taken up in 5% MeOH/DCM (60 mL) and the organic phase was extracted with dilute brine (2×8 mL), then was dried over sodium sulfate and concentrated. The residue was purified by chromatography (3.5% MeOH/DCM) to afford (R,E)-N′-(3-bromo-7-(2-fluoropyridin-3-yl)-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazin]-2′-yl)-N,N-dimethylformimidamide (394 mg, 0.793 mmol).

Provenance & Evidence