Water → 5,6-dihydro-2-(2-phenylethyl)-6-(2-pyridinecarboxamido)-4H-imidazo[4,5,1-ij]quinoline

HRID 341842ノート

反応式

HRID 341842 の反応式
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([NH2:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](Cl)=[O:36].O>ClCCl>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([NH:21][C:35]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=5)=[O:36])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 135033Picolinoyl Chloride HydrochlorideHCID 158384675,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine

生成物 1

HCID 158384705,6-dihydro-2-(2-phenylethyl)-6-(2-pyridinecarboxamido)-4H-imidazo[4,5,1-ij]quinoline収率 56.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A portion (0.4 g) of the 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine obtained in Step 2 of Example 17 was dissolved in anhydrous dichloromethane (5 mL); following the addition of pyridine (0.26 mL), picolinoyl chloride hydrochloride (0.28 g) was added under cooling with ice. After stirring for 4 hrs at room temperature, water (50 mL) and dichloromethane (50 mL) were added to the reaction solution and then two layers were separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to yield the titled compound as pale brown crystals (0.31 g).

後処理

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customtwo layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

出典と根拠

ORDレコード
ord-8e13087f30884f59acfc9cc869977142
出典データセット
uspto-grants-1999_01
特許番号
US05856334

反応ノート

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