1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide

HRID 557380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557380
[F:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.[C:12](NC1C=CC=CC=1)([CH3:15])([CH3:14])[CH3:13].[CH:23]1[CH:24]=[CH:25][C:26]2[N:31](O)N=N[C:27]=2[CH:28]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:12]([C:23]1[CH:28]=[CH:27][C:26]([NH:31][C:8](=[O:10])[C:7]2[CH:6]=[CH:5][C:4]([F:11])=[N:3][C:2]=2[F:1])=[CH:25][CH:24]=1)([CH3:15])([CH3:14])[CH3:13]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 105830702,6-Difluoropyridine-3-carboxylic acid

Produkt 1

HCID 22249203N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2,6-difluoropyridine-3-carboxylic acid (3.2 g, 20 mmol), t-butylaniline (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmol), and DIEA (8 mL) in CH2Cl2 (80 mL) was stirred at RT for 1 h. The mixture was washed with aq. NaHCO3 and brine. The organic solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica (Hex:EtOAc=4:1) to give a light yellow flaky crystal as desired product.

Aufarbeitung

  1. washThe mixture was washed with aq. NaHCO3 and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified via flash chromatography on silica (Hex:EtOAc=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-8571d5a7180245d291cb94ce8efe236a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058445B2

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