Reaktion #43636

Reaktionsgleichung

triacetoxyborohydride

sodium bicarbonate

(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde

→

title compound

(4R)-4-[(4-{[(7-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

Lösungsmittel

dichloromethane

methanol

Reaktionsbedingungen

Vorschrift

A mixture of (4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 1 (50 mg, 016 mmol) and 7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003064421, Example 15(c) (33 mg, 0.16 mmol) in anhydrous dichloromethane (1.5 mL) and anhydrous methanol (0.1 mL) was treated with triacetoxyborohydride (105 mg, 0.49 mmol). After 16 hours, an aqueous solution of sodium bicarbonate was added. The free base of the title compound came out of solution and was isolated by filtration, washed with water and dried in vacuo (50 mg, 60%).

Quelle