反应 #1726712

反应方程式

4-piperidone

3-hydroxy-2-naphthalenecarboxamide

morpholine

→

Compound 159

spiro[2H-naphtho[2,3-e]-1,3-oxazin-2,4′-piperidin]-4-(3H)-one

溶剂

ethyl acetate

toluene

methanol

反应条件

后处理

1. 1
   温度is refluxed for 20 hr
2. 2
   洗涤washed with water, brine
3. 3
   干燥dried over Na2SO4
4. 4
   其他After solvent removal by rotoevaporation
5. 5
   其他the crude product is purified by preparative TLC

实验过程

A mixture of 26 mg (0.083 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone (prepared as described in Example 44), 15.5 mg (0.083 mmol) of 3-hydroxy-2-naphthalenecarboxamide, and 0.020 mL of morpholine in a mixture of 0.2 mL of toluene and 0.6 mL of methanol is refluxed for 20 hr. The reaction mixture is diluted with ethyl acetate, and washed with water, brine, and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 11 mg (0.023 mmol, 27% yield) of 1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]spiro[2H-naphtho[2,3-e]-1,3-oxazin-2,4′-piperidin]-4-(3H)-one (Compound 159): 1H NMR (DMSO-d6): δ 3.95 (s, 3H), 4.07 (s, 3H), 7.20 (s, 1H), 7.23 (d, 1H), 7.44 (d of d, 1H), 7.55 (m, 3H), 7.67 (d, 1H), 8.04 (d, 1H), 8.46 (s, 1H), and 9.09 ppm (s, 1H). MS m/z: 484.0 (M+H)+, 506.0 (M+Na)+.

来源