1-Hydroxybenzotriazole → HCID 58049379, Verbindung

HRID 467957

Reaktionsgleichung

Reaktionsgleichung von HRID 467957
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][CH:7]1[CH2:12][CH2:11][S:10][CH2:9][CH2:8]1.[CH3:17][N:18]1[CH:22]=[C:21]([C:23](O)=[O:24])[N:20]=[CH:19]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(N(CC)CC)C.CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]([CH:7]1[CH2:8][CH2:9][S:10][CH2:11][CH2:12]1)[C:23]([C:21]1[N:20]=[CH:19][N:18]([CH3:17])[CH:22]=1)=[O:24]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58049393N-(3-Bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine

Produkt 1

HCID 58049379HCID 58049379, VerbindungAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of N-(3-bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine (1.72 g), 1-methyl-1H-imidazole-4-carboxylic acid (0.71 g), EDC.HCl (1.63 g), HOBt (0.87 g), dimethylformamide (30 mL) and triethylamine (1.8 mL) was stirred overnight at room temperature. The solvent was distilled off under reduced pressure and after extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (1.55 g).

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionafter extraction with ethyl acetate
  3. washthe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtering off the desiccant
  6. concentrationthe solvent was concentrated
  7. customThe residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fd1f98e4a9454810bee3a7bd93a85dda
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623898B2

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