6-[(4R)-4-(Aminomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one → 6-[(4R)-4-({[(2S)-2-Hydroxy-3-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Participants

Reaction Conditions

Reaction Steps

In a mixed solvent (60 ml) of ethanol and water (9:1) were dissolved 6-methoxy-4-[(2R)-oxiran-2-ylmethyl]pyrido[2,3-b]pyrazin-3(4H)-one (2.94 g, 12.60 mmol) and 6-[(4R)-4-(aminomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Reference Example 54; 3.30 g, 12.60 mmol), and the obtained mixture was then stirred in a sealed tube at 60° C. for 15 hours. Thereafter, the reaction solution was cooled in the air, and the solvent was then removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to yield 1.73 g (28%) of the above-captioned compound in the form of a light yellow solid.

Provenance & Evidence