반응 #91977

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

6-(tert-Butoxycarbonylamino)hexanoic acid

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

N,N-diisopropylethylamine

→

title compound

수율 27.8%

tert-Butyl 6-(2-(1-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethylamino)-6-oxohexylcarbamate

수율 27.8%

용매

DMF

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후처리

1. 1
   기타to give a colorless solution
2. 2
   workup.STIRRINGthe mixture was stirred for 2 hours at room temperature
3. 3
   농축The mixture was concentrated in vacuo
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate (5 mL)
5. 5
   workup.STIRRINGstirred for 1 min with cold sodium hydroxide solution (1 N)
6. 6
   기타dried
7. 7
   농축The organic phase was concentrated in vacuo again
8. 8
   기타the residue was purified by flash chromatography (silica gel, 10% methanol in dichloromethane)

실험 절차

6-(tert-Butoxycarbonylamino)hexanoic acid (197 mg, 850 μmol) was combined with DMF (10.9 mL) to give a colorless solution. O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU, 300 mg, 936 μmol) and N,N-diisopropylethylamine (DIEA, 728 μl, 4.25 mmol) were added with stirring in an inert atmosphere. Then 1-(2-(2-aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (Example 1c, 304 mg, 850 μmol) was added and the mixture was stirred for 2 hours at room temperature. The mixture was concentrated in vacuo, dissolved in ethyl acetate (5 mL), stirred for 1 min with cold sodium hydroxide solution (1 N) and dried by passing through ChemElut® (10 g). The organic phase was concentrated in vacuo again and the residue was purified by flash chromatography (silica gel, 10% methanol in dichloromethane) to give the title compound (0.135 g, 23%) as light brown oil; LC-MS (UV peak area, ESI) 83%, 571.5 (MH+).

출처