Pyridinium chloride → 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline

HRID 433174ノート

反応式

HRID 433174 の反応式
[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[NH:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl.N1C=CC=CC=1>N1C=CC=CC=1>[CH2:21]([C:20]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)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

参加物

4

反応物 2

HCID 10176127Pyridinium chlorideHCID 22320422N-(4-[{5-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide

生成物 1

HCID 223205532-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline収率 94.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A round bottom flask was charged with a magnetic stir bar, N-(4-{[5-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide (4.44 g, 11.46 mmol), pyridine hydrochloride (0.13 g, 1.15 mmol), and anhydrous pyridine (50 mL) under a nitrogen atmosphere. The reaction was judged to be complete after stirring at reflux for 1.5 hours. The solution was cooled and partitioned between ethyl acetate and water. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline (4.0 g, 10.82 mmol) as a brown oil which was used without further purification.

後処理

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe solution was cooled
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-513f2bf0b25b4d5695d0fbc59d60be16
出典データセット
uspto-grants-2003_12
特許番号
US06667312B2

反応ノート

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