Triethylamine → 4-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

HRID 606044노트

반응식

HRID 606044 반응식
[OH:1][N:2]=[C:3](Cl)[CH3:4].[Cl:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:23][O:24][CH2:25][CH3:26])[N:19]([CH2:20][C:21]#[CH:22])[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1.C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:23][O:24][CH2:25][CH3:26])[N:19]([CH2:20][C:21]3[O:1][N:2]=[C:3]([CH3:4])[CH:22]=3)[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 69633Ethanimidoyl chloride, N-hydroxy-HCID 862475854-chloro-2-(ethoxymethyl)-1-prop-2-ynyl-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 866168734-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-Hydroxyethanimidoyl chloride (prepared as described in Part D of Example 1, 2.10 g, 22.5 mmol) was added to a solution of 4-chloro-2-(ethoxymethyl)-1-prop-2-ynyl-1H-imidazo[4,5-c]quinoline prepared as described in Part D of Example 3, 5.39 g, 18.0 mmol) and triethylamine (3.70 mL, 27.0 mmol) in dichloromethane (60 mL). The solution was heated at reflux for 16 hours and then was concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution from 7:3 to 2:3 hexanes/ethyl acetate) to provide 4-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (4.21 g) as a white solid.

후처리

  1. customprepared
  2. temperatureThe solution was heated
  3. temperatureat reflux for 16 hours
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 7:3 to 2:3 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-f7cf02884dfa45e38093690c331ec0a7
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915281B2

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