Acetic Acid → HCID 178483709, Verbindung

HRID 1984636

Reaktionsgleichung

Reaktionsgleichung von HRID 1984636
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:18]([C:27]4[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=4)=[N:17][C:15]=3[N:16]=2)[CH2:7][CH2:6]1.FC(F)(F)C(O)=O.[NH:43]1[CH2:48][CH2:47][CH:46]([C:49]2[NH:50][C:51]([C:54]3[CH:59]=[CH:58][N+:57]([O-:60])=[CH:56][CH:55]=3)=[N:52][N:53]=2)[CH2:45][CH2:44]1.CCN(CC)CC.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:18]([C:27]4[CH:34]=[CH:33][C:30]([CH2:31][N:43]5[CH2:48][CH2:47][CH:46]([C:49]6[NH:50][C:51]([C:54]7[CH:59]=[CH:58][N+:57]([O-:60])=[CH:56][CH:55]=7)=[N:52][N:53]=6)[CH2:45][CH2:44]5)=[CH:29][CH:28]=4)=[N:17][C:15]=3[N:16]=2)[CH2:7][CH2:6]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 577139554-(2-{4-[2-(Dimethylamino)ethyl]piperazin-1-yl}-6-phenylpyrido[2,3-d]pyrimidin-7-yl)benzaldehydeHCID 178525687HCID 178525687, Verbindung

Produkt 1

HCID 178483709HCID 178483709, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-{{4-[2-dimethylamino)ethyl]piperazine-1-yl}-6-phenylpyrido[2,3-d]pyrimidin-7-yl)benzaldehyde (6-5) (100 mg, 0.214 mmol) in DMF (5 mL) was added 4-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine 1-oxide trifluoroacetate (B) (92 mg, 0.257 mmol) followed by Et3N (80 μL, 0.51 mmol), AcOH (91 μL, 1.5 mmol) and sodium triacetoxyborohydride (59 mg, 0.28 mmol). The reaction mixture was allowed to stir for 12 hr then diluted with EtOAc and washed with NaHCO3 (sat.), dried with MgSO4, filtered, and concentrated under reduced pressure. The oily residue was purified by reverse phase HPLC (20% MeCN/80% H2O to 47% MeCN/53% H2O) to afford the title compound. LRMS m/z (M+H) Calcd.: 696.9, found 696.1.

Aufarbeitung

  1. washwashed with NaHCO3 (sat.)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe oily residue was purified by reverse phase HPLC (20% MeCN/80% H2O to 47% MeCN/53% H2O)

Quellen und Nachweise

ORD-Eintrag
ord-23c92cc9c8b247d7b5f3fe935a7026c8
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544677B2

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