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Acetic Acid → 3-[7-Ethoxy-3-(3-fluoro-phenylamino)-2,4-dihydro-indeno[1,2-c]pyrazol-6-yloxy]-propan-1-ol

HRID 460359
ノート
印刷プレビュー

反応式

HRID 460359 の反応式
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=O)=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][O:18]C1CCCCO1)[CH3:2].[F:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=S)[CH:29]=[CH:30][CH:31]=1.C[Si](C)(C)[Si](C)(C)C.[Li].[NH2:44][NH2:45].C(O)(=O)C>C(OCC)(=O)C.C1COCC1>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9]3[C:10]2=[N:44][NH:45][C:33]=3[NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=2)=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][OH:18])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 176Acetic AcidHCID 9321HydrazineHCID 98343-Fluorophenyl isothiocyanate2 回HCID 184458066-Ethoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-oneHCID 57425481Lithium hexamethyldisilane

生成物 1

HCID 1784658023-[7-Ethoxy-3-(3-fluoro-phenylamino)-2,4-dihydro-indeno[1,2-c]pyrazol-6-yloxy]-propan-1-ol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 6-Ethoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one (Intermediate AA) (0.100 g, 0.0003 mol), 3-fluorophenyl isothiocyanate (Compound 4a) (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 48 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 384.2 (M+H)+;

後処理

  1. stirringThe reaction mixture was stirred for 48 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

出典と根拠

ORDレコード
ord-fc8a575e0cc74445b882d49375af1e7d
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07196110B2

反応ノート

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