Acetic Acid → HCID 178473893, Verbindung

HRID 1984628

Reaktionsgleichung

Reaktionsgleichung von HRID 1984628
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17]([C:26]4[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=4)=[N:16][C:14]=3[N:15]=2)[CH2:6][CH2:5]1)(=O)C.F[C:35](F)(F)[C:36]([OH:38])=O.[NH:41]1[CH2:46][CH2:45][CH:44]([C:47]2[NH:48][C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=3)=[N:50][N:51]=2)[CH2:43][CH2:42]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>[C:36]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[C:18]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:17]([C:26]4[CH:33]=[CH:32][C:29]([CH2:30][N:41]5[CH2:46][CH2:45][CH:44]([C:47]6[NH:48][C:49]([C:52]7[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=7)=[N:50][N:51]=6)[CH2:43][CH2:42]5)=[CH:28][CH:27]=4)=[N:16][C:14]=3[N:15]=2)[CH2:8][CH2:9]1)(=[O:38])[CH3:35]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 577139444-[2-(4-Acetylpiperazin-1-yl)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehydeHCID 178525658HCID 178525658, Verbindung

Produkt 1

HCID 178473893HCID 178473893, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(4-acetylpiperazin-1-yl)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehyde (3-2; 61 mg, 0.14 mmol) in DMF (5 mL) was added 2-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine trifluoroacetate (58 mg, 0.17 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 residue was purified by silica gel chromatography (100% CH2Cl2 to 85% CH2Cl2/15% MeOH) to afford the title compound. LRMS m/z (M+H) Calcd.: 651.7, found 651.3.

Aufarbeitung

  1. washwashed with NaHCO3 (sat.)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (100% CH2Cl2 to 85% CH2Cl2/15% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8682c367792c4693b4d39c1d3acfd771
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544677B2

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