Potassium Carbonate → alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 547331ノート

反応式

HRID 547331 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl.[OH:8][C:9]([CH3:29])([CH3:28])[CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:22][C:23](=O)[CH2:24][O:25][CH3:26]>O.C(O)C.[Cl-].[Na+].O>[CH3:26][O:25][CH2:24][C:23]1[N:11]([CH2:10][C:9]([CH3:29])([OH:8])[CH3:28])[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 67204879N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride

生成物 1

HCID 15224447alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol収率 90.9%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of potassium carbonate (3.4 g, 24.3 mmol) in water (9 mL) was added to a stirred suspension of N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride (5.5 g, 16.2 mmol) in ethanol (23 mL). The reaction mixture was heated at reflux for 1.5 hours, then was allowed to cool to room temperature. The mixture was concentrated under reduced pressure to yield an aqueous slurry that was diluted with water (50 mL) and a small amount of brine. The mixture was extracted with dichloromethane (2×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude oil was purified by flash chromatography (silica gel, 5% methanol in dichloromethane) to yield 4.2 g of 1-[2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an oil that slowly solidified.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto yield an aqueous slurry that
  5. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude oil was purified by flash chromatography (silica gel, 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-c20867ceaed54832b3c5f76ae567ffbb
出典データセット
uspto-grants-2011_05
特許番号
US07939526B2

反応ノート

読み込み中…