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N-methyl-2-pyrrolidone → 5-Chloro-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamide

HRID 1526216
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1526216
Cl[C:2]1[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([Cl:8])[N:7]=1.[CH3:14][C:15]1[CH:21]=[C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:19]=[CH:18][C:16]=1[NH2:17].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[Cl:8][C:6]1[N:7]=[C:2]([NH:17][C:16]2[CH:18]=[CH:19][C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:21][C:15]=2[CH3:14])[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]=1[CH2:9][CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 219550002-Methyl-4-(morpholin-4-yl)anilineHCID 848199603,5-Dichloro-6-ethylpyrazine-2-carboxamide

Produkt 1

HCID 1176673245-Chloro-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamideAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (630 mg), 2-methyl-4-(morpholin-4-yl)aniline (500 mg), diisopropylethylamine (900 μL), and N-methylpyrrolidone (5 mL) was stirred at 110° C. overnight. The reactant was left to be cooled, and then water was added thereto, followed by extraction with ethyl acetate. 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; hexane:ethyl acetate=8:2→5:5) to obtain 5-chloro-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamide (660 mg) as an orange solid.

Aufarbeitung

  1. waitThe reactant was left
  2. temperatureto be cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=8:2→5:5)

Quellen und Nachweise

ORD-Eintrag
ord-952778bd6e584f7cb915f832f2ac41e4
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09085540B2

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