Triethylamine → 8-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinoline

HRID 598308ノート

反応式

HRID 598308 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][O:30][CH2:31][CH2:32][C:33](Cl)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:33]([CH2:32][CH2:31][O:30][CH3:29])[N:20]([CH3:21])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27597283-Methoxypropanoyl chlorideHCID 670510076-(benzyloxy)-N4-methylquinoline-3,4-diamine

生成物 1

HCID 670509718-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinoline収率 38.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, a solution of 6-benzyloxy-N4-methylquinoline-3,4-diamine (7.88 g, 28.2 mmol), prepared as described in Parts A-F of Example 57, in dichloromethane (300 mL) was cooled to 0° C.; triethylamine (4.2 mL, 30.3 mmol) was added. Methoxypropionyl chloride (3.3 mL, 30.6 mmol) was added dropwise over a period of five minutes, and the reaction was stirred at ambient temperature for 90 minutes. The volatiles were removed under reduced pressure, and the residue was dissolved in ethanol (300 mL) and triethylamine (13 mL) and heated at 75° C. over two nights. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform. The resulting solution was washed with deionized water (3×200 mL) and concentrated under reduced pressure. Small volumes of hexanes and dichloromethane were added, and a white precipitate formed, which was isolated by filtration and washed with hexanes to provide 3.76 g of 8-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinoline as a white solid.

後処理

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol (300 mL)
  3. temperaturetriethylamine (13 mL) and heated at 75° C. over two nights
  4. customThe volatiles were removed under reduced pressure
  5. dissolutionthe residue was dissolved in chloroform
  6. washThe resulting solution was washed with deionized water (3×200 mL)
  7. concentrationconcentrated under reduced pressure
  8. additionSmall volumes of hexanes and dichloromethane were added
  9. customa white precipitate formed
  10. customwhich was isolated by filtration
  11. washwashed with hexanes

出典と根拠

ORDレコード
ord-fbf799672f444431b816cf40c982ee31
出典データセット
uspto-grants-2011_03
特許番号
US07897597B2

反応ノート

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