반응 #91983

반응 방정식

2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxylic acid

TBTU

DIEA

N,O-dimethylhydroxylamine hydrochloride

→

title compound

수율 111.1%

2-(Ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-N-methoxy-N-methyl-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxamide

수율 111.1%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 1 h at room temperature
2. 2
   농축afterwards the mixture was concentrated in vacuo
3. 3
   기타The residue was partitioned between ethyl acetate (40 mL, 2×20 mL) and water (40 mL)
4. 4
   세척The organic phases were washed with water (2×20 mL)
5. 5
   건조dried over MgSO4
6. 6
   농축concentrated in vacuo
7. 7
   기타purified by flash chromatography (silica gel, 50% to 100% ethyl acetate in heptane)

실험 절차

To a solution of 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxylic acid (484 mg, 741 μmol) in DMF (5.19 mL) in an inert atmosphere was added TBTU (357 mg, 1.11 mmol), DIEA (388 μL, 2.22 mmol) and N,O-dimethylhydroxylamine hydrochloride (108 mg, 1.11 mmol) with stirring. The reaction mixture was stirred for 1 h at room temperature and afterwards the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (40 mL, 2×20 mL) and water (40 mL). The organic phases were washed with water (2×20 mL), combined, dried over MgSO4, concentrated in vacuo and purified by flash chromatography (silica gel, 50% to 100% ethyl acetate in heptane) to give the title compound (0.53 g, quant.) as white foam; LC-MS (UV peak area, ESI) 92%, 644.4 (MH+).

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