Acetic Acid → HCID 178466600, 화합물

HRID 1714458노트

반응식

HRID 1714458 반응식
C(O[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15]COC1CCCCO1)[C:9](=O)[CH2:8][CH2:7]2)C.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([N:34]=[C:35]=S)[CH:31]=[CH:32][CH:33]=1)[CH3:26].[CH3:37][Si](C)(C)[Si](C)(C)C.[Li].[NH2:46][NH2:47].[C:48]([OH:51])(=[O:50])[CH3:49]>C(OCC)(=O)C.C1COCC1>[CH2:14]([O:13][C:12]1[CH:11]=[C:10]2[C:6](=[CH:5][C:4]=1[O:50][CH:48]([OH:51])[CH2:49][CH2:35][NH:34][C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([O:27][CH2:25][CH3:26])[CH:29]=1)[C:7]1=[N:46][NH:47][CH:37]=[C:8]1[CH2:9]2)[CH3:15]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 9321HydrazineHCID 18445696HCID 18445696, 화합물2회HCID 234244901-Ethoxy-3-isothiocyanatobenzene2회HCID 57425481Lithium hexamethyldisilane

생성물 1

HCID 178466600HCID 178466600, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 5-Ethoxy-6-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one (Intermediate Z) (0.100 g, 0.0003 mol), 3-ethoxyphenyl isothiocyanate (Compound 69a) (0.043 mL, 0.00036 mol) and THF (3 mL) was added lithium hexamethyldisilane (0.360 mL, 0.00036 mol) dropwise at room temperature with stirring. The reaction mixture was stirred for 5 h. Hydrazine (0.011 mL, 0.00036 mol) and acetic acid (0.021 mL, 0.00036 mol) was added to the reaction mixture, which was then heated at reflux temperature for 12 h. The reaction solution was then diluted with ethyl acetate, washed with water and dried over MgSO4. The solvent was removed in vacuo and the crude material was purified on the reverse phase HPLC and converted to the desired product upon standing in the 0.1% TFA solution. Lyophilization yielded the title compound as a white powder. MS m/z 410.2 (M+H)+;

후처리

  1. stirringThe reaction mixture was stirred for 5 h
  2. temperaturewas then heated
  3. temperatureat reflux temperature for 12 h
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe crude material was purified on the reverse phase HPLC

출처 및 근거

ORD 기록
ord-5eb9ce3a2a5f4060a9465a80520c226a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795440B2

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