Diisopropylethylamine → 2-Bromo-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide

HRID 467959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467959
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[Br:20][C:21]1[N:22]([CH3:29])[CH:23]=[C:24]([C:26](O)=[O:27])[N:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:20][C:21]1[N:22]([CH3:29])[CH:23]=[C:24]([C:26]([N:8]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[C:4]([O:3][C:2]([F:18])([F:1])[F:19])[CH:5]=2)=[O:27])[N:25]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 510638082-Bromo-1-methyl-1H-imidazole-4-carboxylic acidHCID 58049381N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine

Produkt 1

HCID 469166852-Bromo-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamideAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of N-[3-(trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (190 mg), 2-bromo-1-methyl-1H-imidazole-4-carboxylic acid (100 mg), HATU, diisopropylethylamine (190 mg) and acetonitrile (3 mL) was stirred overnight at room temperature. Acetonitrile was distilled off under reduced pressure and the residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=3:1 to 1:2) to give the titled compound (130 mg).

Aufarbeitung

  1. distillationAcetonitrile was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=3:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-d44b65a5676d4218840e159c902e3197
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623898B2

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