反応 #91973

反応方程式

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

収率 85.0%

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

収率 85.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他to give a colorless solution
2. 2
   workup.ADDITIONwere added
3. 3
   その他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
   その他were separated
8. 8
   抽出The aqueous layer was extracted with ethyl acetate
9. 9
   乾燥The organic phases were combined dried over Na2SO4
10. 10
    ろ過filtered
11. 11
    濃縮concentrated in vacuo
12. 12
    その他The residue was purified by flash chromatography (silica gel-NH2, 0% to 10% methanol in DCM)

実験手順

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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