Hydrochloric Acid → 4-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine

HRID 1850015노트

반응식

HRID 1850015 반응식
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:17]=[C:18]([O:25][C:26]4[CH:27]=[C:28]([NH:32]C(=O)C=C)[CH:29]=[CH:30][CH:31]=4)[C:19]4[S:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1>C(O)C.[Fe]>[NH2:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[O:25][C:18]1[C:19]2[S:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([N:6]3[CH2:5][CH2:4][N:3]([CH3:2])[CH2:8][CH2:7]3)=[CH:14][CH:13]=2)[N:17]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 54758501Olmutinib

생성물 1

HCID 895474154-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine수율 67.8%

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 702Ethanol용매2회

반응 조건

온도
100 °C

실험 절차

Iron (27.1 mmol) and 12 N HCl aqueous solution (2.17 mmol) were diluted with 50% ethanol aqueous solution (30 mL), followed by stirring at 100° C. for 10 min. The compound (5.42 mmol) obtained in Step 4 was dissolved in 50% ethanol aqueous solution (30 mL) and then added to the reaction flask in which iron was activated, followed by stirring at 100° C. for 1 hour. After the reaction was complete, the reaction mixture was filtered with celite to remove iron, and the filtrate was distilled under a reduced pressure. The residue was distilled with dichloromethane and washed with sat. NaHCO3 aqueous solution. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure. The residue was separated by column chromatography (dichloromethane:methanol=10:1 (volume ratio)) to obtain the title compound (yield: 67.8%).

후처리

  1. stirringby stirring at 100° C. for 1 hour
  2. filtrationthe reaction mixture was filtered with celite
  3. customto remove iron
  4. distillationthe filtrate was distilled under a reduced pressure
  5. distillationThe residue was distilled with dichloromethane
  6. washwashed with sat. NaHCO3 aqueous solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationdistilled under a reduced pressure
  10. customThe residue was separated by column chromatography (dichloromethane:methanol=10:1 (volume ratio))

출처 및 근거

ORD 기록
ord-8f023f36bb1d40f19fc097177c0fe7fe
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957065B2

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