2-Methylpentane → (R)-1-(Pyridazin-3-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192310
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:24][CH2:25][C:26]([NH:28][C:29]1[N:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:27].C(OCC)(=O)C.CCCC(C)C>C(#N)C>[Br-:24].[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([NH:28][C:26]([CH2:25][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:27])[N:30]=1

Komponenten

6

Edukt 4

HCID 78922-MethylpentaneHCID 8857Ethyl AcetateHCID 574315532-Bromo-N-pyridazin-3-yl-acetamideHCID 58348375HCID 58348375, Verbindung

Produkt 1

HCID 44516986(R)-1-(Pyridazin-3-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Thiophen-2-yl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 5d) (80 mg) and 2-bromo-N-pyridazin-3-yl-acetamide (Example 5e) (52 mg) were dissolved in acetonitrile (3 mL) and stirred overnight. Ethyl acetate (9 mL) and isohexane (4 mL) were added and stirred overnight. The resulting crystals were filtered off and then triturated with ethyl acetate to afford the titled compound (14 mg).

Aufarbeitung

  1. stirringstirred overnight
  2. filtrationThe resulting crystals were filtered off
  3. customtriturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c6bfc223041e4668b782e43772e947d5
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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