m-Chloroperbenzoic acid → HCID 69506693、化合物

HRID 2366728ノート

反応式

HRID 2366728 の反応式
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23]C)=[O:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].C1C=C(Cl)C=C(C(OO)=O)C=1.ClC(Cl)(Cl)C([N:42]=C=O)=O.[N-]=C=O>CO>[NH2:42][C:9]1[C:8]2[N:17]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:6]([CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH3:23])=[O:21])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

参加物

6

反応物 4

HCID 70297m-Chloroperbenzoic acidHCID 76400Trichloroacetyl isocyanate3 回HCID 105034IsocyanateHCID 69506740HCID 69506740、化合物

生成物 1

HCID 69506693HCID 69506693、化合物収率 103.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A modification of the methods described in Part B of Example 60 was used to treat ethyl 3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate (11.0 g, 31 mmol) with mCPBA (13.6 g of 77% pure material), followed by trichloroacetyl isocyanate (4.4 mL, 37 mmol). The reaction with the isocyanate was stirred for 1.5 hours before the addition of additional trichloroacetyl isocyanate (4.4 mL) and stirring for three days. Additional trichloroacetyl isocyanate (0.5 mL) was added, and the reaction was stirred for four hours. After the addition of methanol (50 mL), the solution was stirred overnight, and then the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (150 mL), and the solution was washed with saturated aqueous sodium bicarbonate (2×35 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 2 mL ammonium hydroxide per liter of eluent) to provide 11.4 g of methyl 3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as a semi-solid.

後処理

  1. stirringthe reaction was stirred for four hours
  2. stirringthe solution was stirred overnight
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (150 mL)
  5. washthe solution was washed with saturated aqueous sodium bicarbonate (2×35 mL)
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 2 mL ammonium hydroxide per liter of eluent)

出典と根拠

ORDレコード
ord-e2b80a57cd3d411cb630d72cf9b38146
出典データセット
uspto-grants-2014_04
特許番号
US08697873B2

反応ノート

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