Tetrahydrofuran → HCID 66924319, Verbindung

HRID 1360202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360202
ClC(Cl)(Cl)[C:3]1[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:17][CH:18]3[CH:25]4[CH2:26][C:21]5([OH:28])[CH2:22][CH:23]([CH2:27][CH:19]3[CH2:20]5)[CH2:24]4)=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[N:4]=1.[CH2:31]([NH2:33])[CH3:32].CO.C(OCC)(=O)C.O1CCCC1>CN1CCCC1=O.O>[CH2:31]([NH:33][C:3]1[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:17][CH:18]3[CH:19]4[CH2:20][C:21]5([OH:28])[CH2:22][CH:23]([CH2:24][CH:25]3[CH2:26]5)[CH2:27]4)=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[N:4]=1)[CH3:32]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 66924168HCID 66924168, VerbindungHCID 86635283HCID 86635283, Verbindung

Produkt 1

HCID 66924319HCID 66924319, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a solution of 4-({5-[5-(trichloromethyl)-1,2,4-oxadiazole-3-yl]-1H-pyrrolo[2,3-b]pyridine-4-yl}amino) adamantan-1-ol (80 mg) in 1-methyl-2-pyrrolidinone (1.6 ml) was added ethylamine/methanol solution (2.0M) (1.7 ml) under ice cooling. The reaction solution was stirred for 5 hours under ambient temperature. To the reaction solution were added ethyl acetate, tetrahydrofuran, and water. The mixture was extracted with a mixture solvent of tetrahydrofuran and ethyl acetate, and washed with saturated brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel (NH silica gel) column chromatography (chloroform:methanol=100:0 to 91:9) to obtain 4-({5-[5-(ethylamino)-1,2,4-oxadiazole-3-yl]-1H -pyrrolo[2,3-b]pyridine-4-yl}amino)adamantan-1-ol (50 mg) as a yellow solid.

Aufarbeitung

  1. extractionThe mixture was extracted with a mixture solvent of tetrahydrofuran and ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel (NH silica gel) column chromatography (chloroform:methanol=100:0 to 91:9)

Quellen und Nachweise

ORD-Eintrag
ord-d4a9395292e74f5c8cf20267b1527566
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879844B2

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