反応 #43624

反応方程式

Sodium cyanoborohydride

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

1

3-hydroxy-piperidin-4-yl-carbamic acid tert-butyl ester

chloroform

2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-7-carboxaldehyde

→

title compound

収率 39.0%

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

収率 39.0%

溶媒

methanol

反応条件

後処理

1. 1
   ろ過The mixture was filtered
2. 2
   その他evaporated
3. 3
   洗浄Chromatography on silica, eluting with 0-20% methanol/dichloromethane

実験手順

(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, 0.166 mmol) and 2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-7-carboxaldehyde (for a synthesis see WO2004058144 Example 48(e)) (32 mg, 0.166 mol) were stirred in chloroform (1 mL) and methanol (1 mL) for 2 h at room temperature. Sodium cyanoborohydride (40 g) was added and the mixture was stirred for 18 h. The mixture was filtered and evaporated. Chromatography on silica, eluting with 0-20% methanol/dichloromethane, gave the free base of the title compound (31 mg, 39%).

出典