Water → N-Cyclobutyl-N-{1-[2-(4-fluorophenyl)pyridin-4-yl]ethyl}-1-methyl-1H-imidazole-4-carboxamide

HRID 1026766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026766
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([NH:16][CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]1[CH:26]=[C:25]([C:27](Cl)=[O:28])[N:24]=[CH:23]1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH:17]1([N:16]([CH:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:13]=2)[CH3:15])[C:27]([C:25]2[N:24]=[CH:23][N:22]([CH3:21])[CH:26]=2)=[O:28])[CH2:20][CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 513419821-Methyl-1H-imidazole-4-carbonyl chlorideHCID 86690484N-{1-[2-(4-Fluorophenyl)pyridin-4-yl]ethyl}cyclobutaneamine

Produkt 1

HCID 86690493N-Cyclobutyl-N-{1-[2-(4-fluorophenyl)pyridin-4-yl]ethyl}-1-methyl-1H-imidazole-4-carboxamideAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of N-{1-[2-(4-fluorophenyl)pyridin-4-yl]ethyl}cyclobutaneamine (100 mg), 1-methyl-1H-imidazole-4-carbonyl chloride (110 mg) and triethylamine (100 mg) in chloroform (5 mL) was stirred at room temperature overnight. Water was added thereto, followed by extraction with chloroform, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) to afford the title compound (120 mg).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100)

Quellen und Nachweise

ORD-Eintrag
ord-fba5a650c5874ab7be5658fd73840216
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729271B2

Notizen zur Reaktion

Wird geladen…