Acetic Anhydride → HCID 57974361, Verbindung

HRID 1864344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864344
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][NH:9][C@H:10]([CH3:39])[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[C:26]([CH3:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:8][N:9]([C@H:10]([CH3:39])[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[C:26]([CH3:38])[CH:25]=1)=[N:16][CH:17]=[N:18]2)[C:1](=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 69064879HCID 69064879, Verbindung

Produkt 1

HCID 57974361HCID 57974361, VerbindungAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Acetic anhydride (66 μl, 0.70 mmol) was added drop wise to a solution of 5-{[(2R)-2-(methylamino)propyl]oxy}-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (250 mg, 0.58 mmol, obtained as described in Example 115, preparation of starting materials) and potassium carbonate (161 mg, 1.16 mmol) in acetone (10 ml). The mixture was stirred at room temperature for 2 hours. After evaporation of the solvents, the residue was diluted in DCM. The solution washed with aqueous sodium bicarbonate and dried over magnesium sulfate. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 2 to 5% 7N ammonia-methanol in DCM) to give the title compound (230 mg, 84%); NMR Spectrum: (CDCl3) 1.28 (d, 3H), 1.94 (s, 3H), 2.30 (s, 3H), 2.53 (s, 3H), 2.90 (s, 3H), 4.30-4.10 (m, 2H), 5.38 (m, 1H), 6.92 (m, 2H), 7.08 (d, 1H), 7.14 (dd, 1H), 7.48 (d, 2H), 7.53 (s, 1H), 7.64 (t, 1H), 8.27 (d, 1H), 8.60 (s, 1H), 9.51 (s, 1H); Mass spectrum: MH+ 472.

Aufarbeitung

  1. customAfter evaporation of the solvents
  2. additionthe residue was diluted in DCM
  3. washThe solution washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents
  6. customthe residue was purified by chromatography on silica gel (eluant: 2 to 5% 7N ammonia-methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-671891d25694480289815b602b3a3a37
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625908B2

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