反应 #43604

反应方程式

4-bromobenzoyl chloride

sodium bicarbonate

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

2

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

triethylamine

→

4-bromo-N-(1-{[(4S)-3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)benzamide

收率 87.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度cooled under argon
2. 2
   其他separated
3. 3
   萃取the aqueous re-extracted twice with 15% methanol/dichloromethane
4. 4
   其他The combined organic extracts were dried
5. 5
   其他evaporated
6. 6
   其他the residue chromatographed

实验过程

A solution of 4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 2 (200 mg, 0.664 mmol) in dichloromethane (5 ml) was treated with triethylamine (0.139 ml, 1 mmol), ice-cooled under argon and treated with 4-bromobenzoyl chloride (150 mg, 0.682 mmol). The solution was shaken with excess aqueous sodium bicarbonate solution, separated and the aqueous re-extracted twice with 15% methanol/dichloromethane. The combined organic extracts were dried and evaporated and the residue chromatographed using dichloromethane/methanol/0.88 ammonia 96:4:0.4 to give 4-bromo-N-(1-{[(4S)-3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)benzamide (280 mg, 87%).

来源