Acetaldehyde → HCID 44562291, Verbindung

HRID 1865208

Reaktionsgleichung

Reaktionsgleichung von HRID 1865208
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([NH2:26])=[N:21][N:22]2[CH3:25])=[CH:18][CH:17]=1.[CH:27](=O)[CH3:28]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([NH:26][CH2:27][CH3:28])=[N:21][N:22]2[CH3:25])=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 177AcetaldehydeHCID 445622906-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine

Produkt 1

HCID 44562291HCID 44562291, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine (Example 120, 140 mg, 0.40 mmol) in dry DCM (Aldrich, 4.0 mL) at RT were added acetaldehyde (Aldrich, 21.1 mg, 0.48 mmol) followed by NaHB(OAc)3 (Aldrich, 102 mg, 0.48 mmol). After being stirred for 4 h at RT, the reaction was quenched by addition of water. The aqueous layer was extracted with DCM. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (DCM/acetone: 100/0 to 60/40) afforded the title compound. MS (ESI, pos. ion) m/z: 379.3 (M+1). Mass Calc'd for C21H22N4O3: 378.43.

Aufarbeitung

  1. customthe reaction was quenched by addition of water
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (DCM/acetone: 100/0 to 60/40)

Quellen und Nachweise

ORD-Eintrag
ord-3bfd345eb81840b485ef73f474b63ded
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626030B2

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