Trimethyl orthoformate → HCID 57447115、化合物

HRID 2366724ノート

反応式

HRID 2366724 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:22](OC)(OC)OC.C(OC)(OC)(OC)CCC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>>[N:12]1([CH2:13][C:14]([CH3:20])([CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:22]1

参加物

5

反応物 4

HCID 9005Trimethyl orthoformate2 回HCID 1235121,1,1-TrimethoxybutaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57447056HCID 57447056、化合物

生成物 1

HCID 57447115HCID 57447115、化合物

実験手順

Ethyl 3-(3-aminoquinolin-4-ylamino)-2,2-dimethylpropanoate (see Example 26 Parts A through D, 5.3 g, 18 mmol) was treated according to a modification of the method described in Part B of Example 8 using trimethyl orthoformate in lieu of trimethyl orthobutyrate. Prior to the addition of trimethyl orthoformate (3.0 mL, 27 mmol) and pyridinium p-toluenesulfonate (0.050 g), the reaction was heated at reflux for 15 minutes. The reaction was heated at reflux overnight, allowed to cool to ambient temperature, washed with saturated aqueous sodium bicarbonate (2×35 mL), and extracted with water (45 mL) containing 10% hydrochloric acid (5 mL). The acidic extract was made basic with the addition of potassium carbonate and then extracted with dichloromethane (3×50 mL). The combined organic extracts were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 4.3 g of ethyl 3-(1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as an oil.

後処理

  1. additionwas treated
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 15 minutes
  4. temperatureThe reaction was heated
  5. temperatureat reflux overnight
  6. washwashed with saturated aqueous sodium bicarbonate (2×35 mL)
  7. extractionextracted with water (45 mL)
  8. additioncontaining 10% hydrochloric acid (5 mL)
  9. extractionThe acidic extract
  10. additionwas made basic with the addition of potassium carbonate
  11. extractionextracted with dichloromethane (3×50 mL)
  12. dry with materialThe combined organic extracts were dried over potassium carbonate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5776b56ec32c4cd3941e645020e0f270
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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