Ethyl orthoformate → HCID 69192155, 화합물

HRID 1187398노트

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HRID 1187398 반응식
[CH:1](OCC)(OCC)OCC.Cl.N1C=CC=CC=1.[C:18]([O:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[N:29]=[CH:28][C:27]=1[NH2:36])(=[O:20])[CH3:19]>C1(C)C=CC=CC=1.ClCCl>[C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26]2[C:35]3[N:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:29]=[CH:28][C:27]=2[N:36]=[CH:1]1)(=[O:20])[CH3:19]

참가 물질

6

반응물 3

HCID 31214Ethyl orthoformate2회HCID 10176127Pyridinium chlorideHCID 68539256HCID 68539256, 화합물

생성물 1

HCID 69192155HCID 69192155, 화합물수율 91.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

Triethyl orthoformate (1.86 mL, 17.0 mmol) and pyridine hydrochloride (0.164 g, 1.42 mrnmol) were added to a stirred suspension of 3-[(3-amino[1,5]naphthyridin-4-yl)amino]propyl acetate (prepared as described in Part C of Examples 127-135, 3.70 g, 14.2 mmol) in toluene (70 mL). The mixture was heated at reflux with a Dean-Stark trap. After 2.5 hours, additional triethyl orthoformate (1 mL) was added and heating was continued for another 2 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure to afford a dark oil that was dissolved in dichloromethane (100 mL). The solution was washed with saturated aqueous sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 3.50 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl acetate as an orange oil that was used without further purification in the next step.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux with a Dean-Stark trap
  3. temperatureheating
  4. waitwas continued for another 2 hours
  5. concentrationwas concentrated under reduced pressure
  6. customto afford a dark oil that
  7. washThe solution was washed with saturated aqueous sodium bicarbonate (50 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-665b643b3cdb4fbaaa43d69673013a53
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673932B2

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