Diisopropylethylamine → HCID 117667243, Verbindung

HRID 1526250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526250
Cl[C:2]1[C:3]([C:13]([NH2:15])=[O:14])=[N:4][C:5]([C:9]([OH:12])([CH3:11])[CH3:10])=[C:6]([Cl:8])[N:7]=1.[NH2:16][C:17]1[CH:18]=[N:19][N:20]([CH2:22][CH2:23][OH:24])[CH:21]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>O1CCOCC1>[Cl:8][C:6]1[N:7]=[C:2]([NH:16][C:17]2[CH:18]=[N:19][N:20]([CH2:22][CH2:23][OH:24])[CH:21]=2)[C:3]([C:13]([NH2:15])=[O:14])=[N:4][C:5]=1[C:9]([OH:12])([CH3:11])[CH3:10]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 86662050HCID 86662050, Verbindung

Produkt 1

HCID 117667243HCID 117667243, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dichloro-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (2.0 g), 2-(4-amino-1H-pyrazol-1-yl)ethan-1-ol (1.12 g), diisopropylethylamine (2.79 mL), and dioxane (20 mL) was heated and refluxed for 2 hours. The reactant was cooled, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with a mixture of chloroform:methanol (10:1). The organic phase was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10) to obtain 5-chloro-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (1.69 g) as a yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturerefluxed for 2 hours
  3. temperatureThe reactant was cooled
  4. extractionfollowed by extraction with a mixture of chloroform:methanol (10:1)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10)

Quellen und Nachweise

ORD-Eintrag
ord-bae13a200cfd49d8831e023bd6ae69e5
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085540B2

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