反应详情

温度

0 °C

To a solution of CH2Cl2 (35 ml) and trifluoroacetic anhydride (3.6 ml, 0.0224 mol) at -78° C. is added CH2Cl2 (5 ml) and DMSO (3.22 ml, 0.0454 mol). The reaction mixture is stirred for 1 hour, then a solution of 1-ethyl-6-methoxy-N-(4-hydroxycyclohexylmethyl)-1H-pyrazolo-[3,4-b]quinolin-4-amine (1.8 g, 0.0051 mol) in CH2Cl2 (30 ml) is added, and the reaction mixture is slowly warmed to 0° C. with stirring overnight. The reaction mixture is cooled to -78° C. and triethylamine (11 ml, 0.075 mol) is added. The reaction mixture is warmed to room temperature, stirred for 5 hours and then poured into water. The mixture is extracted with CH2Cl2 and the CH2Cl2 extracts are combined, washed with water, dried over MgSO4 and evaporated. The residue is purified by column chromatography on silica gel eluting with ethyl acetate to afford the product as the free base. The free base is dissolved in 2-propanol and methanesulfonic acid is added. The volume is reduced to about 5 ml, ether is added and the precipitated salt is collected by filtration and recrystallized from 2-propanol/ether to afford 1 g of 1-ethyl-6-methoxy-N-[4-oxocyclohexylmethyl]-1H-pyrazolo[3,4-b]quinolin-4-amine. CH3SO3H. 1/2 H2O.

1. stirringwith stirring overnight
2. temperatureThe reaction mixture is cooled to -78° C.
3. temperatureThe reaction mixture is warmed to room temperature
4. stirringstirred for 5 hours
5. extractionThe mixture is extracted with CH2Cl2
6. washwashed with water
7. dry with materialdried over MgSO4
8. customevaporated
9. customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate
10. customto afford the product as the free base
11. additionis added
12. filtrationthe precipitated salt is collected by filtration
13. customrecrystallized from 2-propanol/ether