Phosphorus trichloride → 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride

HRID 1818195

反応式

HRID 1818195 の反応式
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][O:32][CH2:33][CH3:34])[N:14]([CH2:15][CH2:16][N+:17]3([O-])[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([Br:35])=[CH:5][C:4]=2[N:3]=1.P(Cl)(Cl)[Cl:37]>C(Cl)(Cl)Cl.O>[ClH:37].[ClH:37].[Br:35][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:13]([CH2:31][O:32][CH2:33][CH3:34])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

参加物

5

反応物 2

HCID 24387Phosphorus trichlorideHCID 21984440tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate

生成物 1

HCID 219841297-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride収率 84.2%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 6212Chloroform溶媒

反応条件

温度
4 °C

実験手順

A solution of tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate (8.84 g, 16.1 mmol) in chloroform (400 mL) was cooled to 4° C. Phosphorous trichloride (9.82 mL, 113 mmol) was added dropwise, and the reaction was stirred for 45 minutes at 4° C. Water (one drop) was added to the reaction, which was allowed to warm to ambient temperature. The chloroform was removed under reduced pressure, and the residue was dissolved in ethanol (150 mL). Hydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added, and the reaction was heated at reflux for 25 minutes. The reaction was allowed to cool to room temperature; a precipitate formed and was isolated by filtration to provide 6.86 g of 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride as a light yellow solid.

後処理

  1. temperatureto warm to ambient temperature
  2. customThe chloroform was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (150 mL)
  4. additionHydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added
  5. temperaturethe reaction was heated
  6. temperatureat reflux for 25 minutes
  7. temperatureto cool to room temperature
  8. customa precipitate formed
  9. customwas isolated by filtration

出典と根拠

ORDレコード
ord-da1b1d39c0cc4e3e8b4ea09cb1fe740b
出典データセット
uspto-grants-2009_10
特許番号
US07598382B2

関連ノート

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