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

HRID 606044

反応式

HRID 606044 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f7cf02884dfa45e38093690c331ec0a7
出典データセット
uspto-grants-2011_03
特許番号
US07915281B2

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