Diisopropylethylamine → N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide

HRID 253967

Reaktionsgleichung

Reaktionsgleichung von HRID 253967
[C:1]([NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[F:22][C:23]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[C:1]([NH:5][C:6]1[C:11]([NH:12][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:23]=2[F:22])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5195492,3-Difluorobenzoyl chlorideHCID 15656135HCID 15656135, Verbindung

Produkt 1

HCID 59003070N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N2-tert-butylpyridine-2,3-diamine in dry DCM (150 mL) was added DIEA (17 mL, 95.5 mmol). The solution was cooled to 0° C. and carefully added 2,3-difluorobenzoyl chloride (8.35 g, 47.30 mmol). The reaction was allowed to warm up to RT and stirred for 1 hr. The mixture was then washed with water, saturated NaHCO3, and dried over MgSO4. Removal of the solvent by evaporation, the residue was purified by silica gel chromatography (5%-60% EtOAc/hexane) to yield N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide (4.0 g, 13.10 mmol); LC-MS m/e=306.1 (M+H).

Aufarbeitung

  1. temperatureto warm up to RT
  2. washThe mixture was then washed with water, saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. customby evaporation
  6. customthe residue was purified by silica gel chromatography (5%-60% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ef7d54834db9401fa8d9e04131ed7fd6
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872031B2

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