[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][C:13](=O)[NH:14][C:9]=3[CH:8]=2)[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][CH2:13][NH:14][C:9]=3[CH:8]=2)[CH:2]=1
7-pyridin-3-yl-1H-pyrido[2,3-b][1,4]oxazin-2-one (60 mg, 0.264 mmol) was dissolved in 4 ml of anhydrous tetrahydrofuran under nitrogen atmosphere, and the mixture was cooled to 0□, and 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (0.7 ml, 0.704 mmol) was added thereto dropwise at room temperature for 5 hours. To the reaction mixture, water (0.3 ml), 10% sodium hydroxide (0.6 ml) and water (0.9 ml) were added dropwise in this order, and then stirred vigorously at room temperature for 1 hour. The formed solid was filtered and washed with excess ethyl acetate. The filtrate was washed with water and saturated saline solution, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to obtain 7-pyridin-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine as white solid (30 mg, 53%).
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