Acetic Acid → 1-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine

HRID 1057307

Reaktionsgleichung

Reaktionsgleichung von HRID 1057307
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[N:24]=[C:25]([C:28]3[CH:29]=[CH:30][C:31]([N:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)=[N:32][CH:33]=3)[NH:26][CH:27]=2)[CH:19]=[CH:20][C:21]=1[Cl:22].C(O)(=O)C.[CH:44](=O)[CH:45]([CH3:47])[CH3:46]>C1COCC1.[OH-].[Na+].C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[NH:24][C:25]([C:28]3[CH:29]=[CH:30][C:31]([N:34]4[CH2:39][CH2:38][N:37]([CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:36][CH2:35]4)=[N:32][CH:33]=3)=[N:26][CH:27]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178477952{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine

Produkt 1

HCID 98673341-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (20.2 g) was added to a suspension of 1-{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine (23.8 g), acetic acid (5.1 mL), and isobutyraldehyde (6.35 mL) in THF (250 mL). The resultant suspension was stirred at ambient temperature for 18 hours, and then the reaction mixture was diluted with 1N NaOH (1000 mL) and ethyl acetate (450 mL). The layers were separated, and the organic phase was diluted with hexanes (1000 mL). The resultant precipitate was collected by filtration, and the mother liquors were concentrated to 400 mL. The second crop of precipitate was collected and combined with the first crop to provide 1-{5-[5-(3,4,-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine (22.5 g). MS m/z 430 (M++1).

Aufarbeitung

  1. customThe layers were separated
  2. additionthe organic phase was diluted with hexanes (1000 mL)
  3. filtrationThe resultant precipitate was collected by filtration
  4. concentrationthe mother liquors were concentrated to 400 mL
  5. customThe second crop of precipitate was collected

Quellen und Nachweise

ORD-Eintrag
ord-1196ddcf437a41eb986db2c4e14ea11c
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514966B2

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