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Hydrochloric Acid → HCID 86646073, Verbindung

HRID 1800679
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1800679
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:12]([NH:14][C:15]2[CH:16]=[C:17]([N:21]([CH3:34])[C:22]3[N:27]=[C:26]([S:28][C:29]#[N:30])[C:25]([N+:31]([O-])=O)=[CH:24][N:23]=3)[CH:18]=[CH:19][CH:20]=2)=[O:13])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4])#[N:2].CN1CCCC1=O.Cl.[OH-].[Na+]>C(O)C>[NH2:30][C:29]1[S:28][C:26]2[N:27]=[C:22]([N:21]([CH3:34])[C:17]3[CH:16]=[C:15]([NH:14][C:12](=[O:13])[C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=4)[CH:20]=[CH:19][CH:18]=3)[N:23]=[CH:24][C:25]=2[N:31]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 86646072HCID 86646072, Verbindung

Produkt 1

HCID 86646073HCID 86646073, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of the above-mentioned crude product of 2-{[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenyl](methyl)amino}-5-nitropyrimidin-4-yl thiocyanate and reduced iron (368 mg, 6.59 mmol) in ethanol (8 mL)/1-methylpyrrolidin-2-one (2 mL) was added 1N hydrochloric acid (2 mL), and the mixture was stirred at 100° C. for 30 min. The reaction mixture was neutralized with 2N aqueous sodium hydroxide solution (1.5 mL), the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate (50 mL, 2×20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/70→10/90), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to give the title compound (211 mg, 36%) as pale-purple crystals.

Aufarbeitung

  1. filtrationthe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL)
  4. extractionthe mixture was extracted with ethyl acetate (50 mL, 2×20 mL)
  5. washThe combined organic layer was washed with saturated brine (10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/70→10/90)
  10. additionthe fractions containing the object product
  11. concentrationwere concentrated under reduced pressure
  12. customThe obtained residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-39c1547ec4bf4bd1a9cef00946174c24
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344135B2

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