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

HRID 547331노트

반응식

HRID 547331 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c20867ceaed54832b3c5f76ae567ffbb
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939526B2

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