6-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine → HCID 67339893, Verbindung

HRID 1674972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674972
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:20]([O:24][C:25](=[O:35])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=1)([CH3:23])([CH3:22])[CH3:21]>C(O)(=O)C.ClCCl>[F:19][C:16]([F:17])([F:18])[C:13]1[N:11]2[N:12]=[C:7]([N:1]3[CH2:2][CH2:3][N:4]([CH2:33][C:30]4[CH:29]=[CH:28][C:27]([NH:26][C:25](=[O:35])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:32][CH:31]=4)[CH2:5][CH2:6]3)[CH:8]=[CH:9][C:10]2=[N:15][N:14]=1

Komponenten

5

Edukt 2

HCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineHCID 2771821tert-Butyl (4-formylphenyl)carbamate

Produkt 1

HCID 67339893HCID 67339893, VerbindungAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.079 g, 0.29 mmol) in a mixture of acetic acid and dichloromethane (1:9; 3 mL) was added to a mixture of (polystyrylmethyl)trimethylammonium cyanoborohydride (4.1 mmol/g, 0.097 g, 0.4 mmol) and N-(4-formylphenyl)carbamic acid tert-butyl ester (0.088.4 g, 0.4 mmol). The reaction mixture was shaken for 4 days and then filtered. The filtrate was evaporated and the and the involatile residue was purified by hplc using a Waters XBridge Prep C18 OBD column (5μ silica, 21 mm diameter, 100 mm length) eluted with decreasingly polar mixtures of water (containing 0.05% aqueous ammonia) and acetonitrile as eluents to give tert-butyl 4-((4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazin-1-yl)methyl)phenylcarbamate (0.0722 g, 52%) as a white solid, which was used without further purification.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe and the involatile residue was purified by hplc
  4. washeluted with decreasingly polar mixtures of water (containing 0.05% aqueous ammonia) and acetonitrile as eluents

Quellen und Nachweise

ORD-Eintrag
ord-01f5edeb81124dbfb88d2d21785dcee1
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003649B2

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