Triethylamine → 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

HRID 1093210노트

반응식

HRID 1093210 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH:9]=O)=[C:4](Cl)[N:3]=1.C(O)(=O)C(O)=O.[CH2:18]([NH:20][NH2:21])[CH3:19].C(N(CC)CC)C.Cl.[CH:30]12[O:37][CH:34]([CH2:35][CH2:36]1)[CH2:33][NH:32][CH2:31]2>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]2[N:20]([CH2:18][CH3:19])[N:21]=[CH:9][C:5]2=[C:6]([N:32]2[CH2:31][CH:30]3[O:37][CH:34]([CH2:35][CH2:36]3)[CH2:33]2)[N:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 109327462,4,6-Trichloro-5-pyrimidinecarboxaldehydeHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

생성물 1

HCID 866293763-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a cloudy solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (1.1 g, 5.2 mmol) in chloroform (50 mL) cooled to −78° C. was added ethylhydrazine oxalate (0.78 g, 5.2 mmol) in two portions, followed by triethylamine (2.7 mL). The cooling bath was then removed and ethanol (10 mL) was added to the reaction mixture, which was allowed to warm to room temperature. 8-Oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.69 g, 4.6 mmol) was added to the mixture. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate. The combined organics were washed successively with 5% aqueous potassium hydrogen sulfate solution, water, saturated aqueous sodium hydrogen carbonate solution, and saturated aqueous sodium chloride solution. Organics were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to provide 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. MS (ES+): 293.9, 295.9 (M+H)+

후처리

  1. customThe cooling bath was then removed
  2. additionethanol (10 mL) was added to the reaction mixture, which
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. washThe combined organics were washed successively with 5% aqueous potassium hydrogen sulfate solution, water, saturated aqueous sodium hydrogen carbonate solution, and saturated aqueous sodium chloride solution
  7. dry with materialOrganics were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e1f24150d7cd4d589678381349adcc87
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129371B2

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