Trimethyl orthoformate → HCID 57447115, 화합물

HRID 2366724노트

반응식

HRID 2366724 반응식
[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

참가 물질

5

반응물 4

HCID 9005Trimethyl orthoformate2회HCID 1235121,1,1-TrimethoxybutaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57447056HCID 57447056, 화합물

생성물 1

HCID 57447115HCID 57447115, 화합물

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5776b56ec32c4cd3941e645020e0f270
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697873B2

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