反应 #91973

反应方程式

1-(2-(2-aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Nicotinic acid

TBTU

DIEA

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title product

收率 85.0%

N-(2-(1-(4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethyl)nicotinamide

收率 85.0%

溶剂

DMF

反应条件

后处理

1. 1
   其他to give a colorless solution
2. 2
   workup.ADDITIONwere added
3. 3
   其他Volatiles were removed in high vacuum at 40° C
4. 4
   workup.DISSOLUTIONThe residue was dissolve in a mixture of ethyl acetate (5 mL) and methanol (0.5 mL)
5. 5
   workup.ADDITION1N sodium hydroxide solution (1.5 mL) was added and after a few minutes
6. 6
   workup.STIRRINGstirring the layers
7. 7
   其他were separated
8. 8
   萃取The aqueous layer was extracted with ethyl acetate
9. 9
   干燥The organic phases were combined dried over Na2SO4
10. 10
    过滤filtered
11. 11
    浓缩concentrated in vacuo
12. 12
    其他The residue was purified by flash chromatography (silica gel-NH2, 0% to 10% methanol in DCM)

实验过程

Nicotinic acid (11.4 mg, 92.3 μmol) was combined with DMF (1.0 mL) to give a colorless solution. To this solution was added TBTU (29.6 mg, 92.3 μmol), and DIEA (54.2 mg, 71.8 μl) were added. Finally 1-(2-(2-aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (30 mg, 83.9 μmol) was added and the reaction mixture was stirred for 1 hour at room temperature. Volatiles were removed in high vacuum at 40° C. The residue was dissolve in a mixture of ethyl acetate (5 mL) and methanol (0.5 mL). 1N sodium hydroxide solution (1.5 mL) was added and after a few minutes stirring the layers were separated. The aqueous layer was extracted with ethyl acetate. The organic phases were combined dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel-NH2, 0% to 10% methanol in DCM) to give the title product (33 mg, 85%) as white foam; LC-MS (UV peak area, ESI) 88%, 463.2459 (MH+).

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