Benzoyl chloride → HCID 23512661、化合物

HRID 353886ノート

反応式

HRID 353886 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:23])[C:13]=2[N:12]=[C:11]1[CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl>[NH2:23][C:14]1[C:13]2[N:12]=[C:11]([CH2:24][CH2:25][CH2:26][CH3:27])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 223444481-(8-Aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 23512661HCID 23512661、化合物収率 46.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-(8-aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 3.26 mmol) and triethylamine (500 μL, 3.59 mmol) in dichloromethane (30 mL) was cooled to 0° C. Benzoyl chloride (380 μL, 3.26 mmol) was slowly added dropwise. The reaction mixture was allowed to slowly warm to ambient temperature. After several hours the reaction mixture was washed with distilled water (1×50 mL) and brine (2×50 mL), dried over sodium sulfate and then concentrated under reduced pressure to provide 1.5 g of crude orange gooey material. This material was purified by column chromatography (65 g of silica gel, eluting with 7.5% methanol in dichloromethane). The purified material was dissolved in a small amount of dichloromethane and the solution was diluted with hexane to precipitate a white powder. This material was isolated by filtration, washed with hexanes and then dried in a vacuum oven at 60° C. overnight to provide 0.72 g of N-[8-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)octyl]benzamide as a white powder, m.p. 149.5-151.3° C. Analysis: Calculated for C29H37N6O: % C, 73.85; % H, 7.91; % N, 14.85. Found: % C, 73.46; % H, 7.79; % N, 14.56.

後処理

  1. washAfter several hours the reaction mixture was washed with distilled water (1×50 mL) and brine (2×50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto provide 1.5 g of crude orange gooey material
  5. customThis material was purified by column chromatography (65 g of silica gel, eluting with 7.5% methanol in dichloromethane)
  6. dissolutionThe purified material was dissolved in a small amount of dichloromethane
  7. additionthe solution was diluted with hexane
  8. customto precipitate a white powder
  9. customThis material was isolated by filtration
  10. washwashed with hexanes
  11. customdried in a vacuum oven at 60° C. overnight

出典と根拠

ORDレコード
ord-4abf6c4f3bf5409f8795827abb7b31f7
出典データセット
uspto-grants-2004_06
特許番号
US06756382B2

反応ノート

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