4-Toluenesulfonyl chloride → 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 540843ノート

反応式

HRID 540843 の反応式
[OH-].[NH4+:2].[CH2:3]([C:5]1[N:6]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:28]=1)[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH2:3]([C:5]1[N:6]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])=[CH:12][C:11]=3[N:10]=[C:9]([NH2:2])[C:8]=2[N:28]=1)[CH3:4]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 689735912-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-5-oxido-1H-imidazo[4,5-c]quinoline

生成物 1

HCID 588336972-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolin-4-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ammonium hydroxide (0.5 mL) was added to a solution of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-5-oxido-1H-imidazo[4,5-c]quinoline (0.53 g, 1.28 mmol) in dichloromethane (3 mL), and the mixture was cooled to 0° C. p-Toluenesulfonyl chloride (0.29 g, 1.5 mmol) was added in small portions over a period of 20 minutes. The reaction was stirred at ambient temperature overnight. The reaction mixture was partitioned between dichloromethane and 1% aqueous sodium carbonate. The organic fraction was washed with 1% aqueous sodium carbonate (2×30 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from ethyl acetate, isolated by filtration, washed with cold hexanes, and dried under high vacuum at 55° C. to provide 0.391 g of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolin-4-amine as off-white needles, mp 219-220° C.

後処理

  1. additionwas added in small portions over a period of 20 minutes
  2. customThe reaction mixture was partitioned between dichloromethane and 1% aqueous sodium carbonate
  3. washThe organic fraction was washed with 1% aqueous sodium carbonate (2×30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was recrystallized from ethyl acetate
  8. customisolated by filtration
  9. washwashed with cold hexanes
  10. customdried under high vacuum at 55° C.

出典と根拠

ORDレコード
ord-253f3c067cfe47d59a0a9d70deeb1ae1
出典データセット
uspto-grants-2014_10
特許番号
US08871782B2

反応ノート

読み込み中…