反応 #996521

反応方程式

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

1,4-butanesultam

(±)-trans-1,2-diaminocyclohexane

potassium phosphate

→

7-(1,1-dioxo-[1,2]thiazinan-2-yl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

収率 55.5%

溶媒

dioxane

反応条件

後処理

1. 1
   その他The vial was flushed with nitrogen
2. 2
   その他sealed with a Teflon-
3. 3
   その他lined cap
4. 4
   その他placed in an oil bath
5. 5
   温度The reaction was cooled to ambient temperature
6. 6
   workup.ADDITIONdiluted with chloroform
7. 7
   ろ過filtered through a bed of CELITE
8. 8
   ろ過filter agent
9. 9
   その他The solvent was evaporated
10. 10
    その他the residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument
11. 11
    その他The purification
12. 12
    洗浄was carried out eluting with chloroform
13. 13
    その他Additional purification
14. 14
    その他by recrystallization from acetonitrile

実験手順

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.75 g), 1,4-butanesultam (0.29 g), copper(I) iodide (68 mg), (±)-trans-1,2-diaminocyclohexane (42 μL), potassium phosphate (0.79 g) and dioxane (4 mL) were added to a scintillation vial. The vial was flushed with nitrogen, sealed with a Teflon-lined cap, placed in an oil bath, and heated at 110° C. for 30 hours. The reaction was cooled to ambient temperature, diluted with chloroform and filtered through a bed of CELITE filter agent. The solvent was evaporated and the residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform:CMA in a gradient from 99:1 to 90:10. Additional purification by recrystallization from acetonitrile provided 0.47 g of 7-(1,1-dioxo-[1,2]thiazinan-2-yl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine as pale yellow crystals, mp 172-174° C.

出典