Acetic Acid → HCID 21906201, Verbindung

HRID 988605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988605
F[C:2](F)(F)[C:3](O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[N:13][CH:14]=1.[C:33](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>CC(C)=O.ClCCCl>[ClH:8].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24]([CH:26]2[CH2:31][CH2:30][N:29]([CH:2]([CH3:3])[CH3:33])[CH2:28][CH2:27]2)=[O:25])=[N:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 21906487HCID 21906487, Verbindung

Produkt 1

HCID 21906201HCID 21906201, VerbindungAusbeute 114,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred suspension of N-(5-chloropyridin-2-yl)-2-[(piperidin-4-ylcarbonyl)amino]benzamide trifluoroacetate (0.4 g, 0.85 mmol) in acetone (6 mL) and 1,2-dichloroethane (10 mL) was added glacial acetic acid (0.2 mL, 3.84 mmol) followed by then sodium triacetoxyborohydride (0.81 g, 3.84 mmol). After stirring for 15 h, saturated aqueous ammonium chloride (10 mL) was added. After stirring for 0.5 h, the mixture was partitioned between dichloromethane and water and the layers separated. The organic phase was washed with saturated aqueous sodium chloride, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was then purified by preparative RPHPLC (C18), eluting with a linear gradient of 90/10 to 60/40 (0.01% HCl/acetonitrile) over 180 min. The product containing fractions were combined and lyophilized to give 0.212 g (57%) of the title compound as a white solid.

Aufarbeitung

  1. stirringAfter stirring for 0.5 h
  2. customthe mixture was partitioned between dichloromethane and water
  3. customthe layers separated
  4. washThe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by preparative RPHPLC (C18)
  9. washeluting with a linear gradient of 90/10 to 60/40 (0.01% HCl/acetonitrile) over 180 min
  10. additionThe product containing fractions

Quellen und Nachweise

ORD-Eintrag
ord-55689c4235544b39b0848a549bb95d33
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635657B1

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