Acetic Acid → HCID 178428391, Verbindung

HRID 80207

Reaktionsgleichung

Reaktionsgleichung von HRID 80207
C(O)(=O)C.[NH2:5][NH2:6].F[C:8]1[CH:9]=[C:10]([N:20]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][C:30]=3[CH3:31])[C:21]2=[O:32])[CH:11]=[CH:12][C:13]=1[C:14](=O)[C:15]([F:18])([F:17])[F:16].CO>C1COCC1.C(Cl)(Cl)Cl>[CH3:31][C:30]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[N:22]1[CH2:23][CH2:24][N:20]([C:10]2[CH:9]=[C:8]3[C:13]([C:14]([C:15]([F:18])([F:17])[F:16])=[N:5][NH:6]3)=[CH:12][CH:11]=2)[C:21]1=[O:32]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 9321HydrazineHCID 596361941-[3-Fluoro-4-(2,2,2-trifluoroacetyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Produkt 1

HCID 178428391HCID 178428391, VerbindungAusbeute 23,46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Acetic acid (0.1 mL, 1.36 mmol) and 1M hydrazine in THF (4 mL, 2.72 mmol) were added to 1-[3-fluoro-4-(2,2,2-trifluoro-acetyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-160b: 100 mg, 0.272 mmol) in dry THF (2 mL). The resulting mixture was stirred at 150° C. overnight. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was partitioned between water and chloroform. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (4% MeOH in CHCl3), followed by preparative HPLC afforded 23 mg of the product (23.46% yield).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and chloroform
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by column chromatography on silica gel (4% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-869e360651c84a5babc1fe50126179d8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

Verknüpfte Notizen

Wird geladen…