3-Methoxypropanoyl chloride → 2-(2-methoxyethyl)-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline

HRID 1182234

반응식

HRID 1182234 반응식
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:19].[CH3:20][O:21][CH2:22][CH2:23][C:24](Cl)=O>N1C=CC=CC=1>[CH3:20][O:21][CH2:22][CH2:23][C:24]1[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1

참가 물질

4

반응물 2

HCID 27597283-Methoxypropanoyl chlorideHCID 22320477N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

생성물 1

HCID 223204842-(2-methoxyethyl)-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline수율 67.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

A round bottom flask was charged with a magnetic stir bar, N4-[5-(methylthio)pentyl]quinoline-3,4-diamine (3.56 g, 12.93 mmol) and anhydrous pyridine (52 mL) under a nitrogen atmosphere. The resulting homogeneous solution was cooled to 0° C. in an ice-water bath. To the cooled solution was added neat 3-methoxypropionyl chloride (2.74 g, 22.36 mmol). After addition of the acid chloride, the reaction was heated to reflux for 14 hours at which time the acylated intermediate was completely consumed. The solution was cooled and then partitioned between chloroform and saturated aqueous ammonium chloride. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford 2-(2-methoxyethyl)-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline (3.0 g, 8.73 mmol) which was isolated as a brown oil and used without further purification.

후처리

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 14 hours at which time the acylated intermediate
  4. customwas completely consumed
  5. temperatureThe solution was cooled
  6. custompartitioned between chloroform and saturated aqueous ammonium chloride
  7. customThe layers were separated
  8. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d381b0919c1446b5bea80ae39930a96c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288550B2

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