Acetic Acid → HCID 59473817, Verbindung

HRID 2069718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069718
[C:1]([O:5][C:6](=[O:25])[N:7]([C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[N:7]([C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:30]2[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]2)=[CH:10][N:9]=1)([CH3:2])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 59473778HCID 59473778, Verbindung

Produkt 1

HCID 59473817HCID 59473817, VerbindungAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.0 g, 2.45 mmol) in DCM (49 ml) was added 1-methylpiperazine (491 mg, 4.9 mmol), sodium triacetoxyborohydride (1.3 g, 6.12 mmol) and acetic acid (294 mg, 4.9 mmol). The reaction mixture was heated to 40 degrees centigrade and stirred overnight. The reaction was diluted with DCM, washed with saturated aqueous sodium bicarbonate, dried and concentrated. The crude product was purified by flash chromatography using a gradient of 0% to 20% methanol in DCM to give 1.08 g (89.5%) of (5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture was heated to 40 degrees centigrade
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-693550f3334d479b9d43a859cf86c040
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299077B2

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