Triethylamine → HCID 57505728, Verbindung

HRID 2391494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2391494
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.[C:24]([C:28]1[CH:32]=[C:31]([NH:33][C:34](=O)[O:35]CC(Cl)(Cl)Cl)[N:30]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:29]=1)([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>CS(C)=O.O.C(OCC)(=O)C>[C:24]([C:28]1[CH:32]=[C:31]([NH:33][C:34]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[N:11]=2)=[O:35])[N:30]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:29]=1)([CH3:27])([CH3:25])[CH3:26]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 45926015HCID 45926015, VerbindungHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 57505728HCID 57505728, VerbindungAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 23503278(Methanesulfinyl)methane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (160 mg, 0.52 mmol) and 2,2,2-trichloroethyl (3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)carbamate (200 mg, 0.52 mmol) in dimethylsulfoxide/water (2.0 mL/1.5 mL) was added triethylamine (53 mg, 0.52 mmol), and the mixture was stirred at 85° C. for 8 hr. The reaction mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid, 5% aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) and precipitated from ethyl acetate/diisopropyl ether/hexane to give the title compound (285 mg, 99%) as a white powder.

Aufarbeitung

  1. washwashed with 1N hydrochloric acid, 5% aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltrated
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)
  6. customprecipitated from ethyl acetate/diisopropyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9d13a9766193424b8bd2f5718919bdce
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273741B2

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