Pyridine → 3-(5-bromo-2-fluorobenzoylamino)pyrazine-2-carboxylic Acid Methyl Ester

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Reaktionsgleichung

N1C=CC=CC=1.[CH3:7][O:8][C:9]([C:11]1[C:16]([NH2:17])=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10].[Br:18][C:19]1[CH:20]=[CH:21][C:22]([F:28])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25]>C(Cl)Cl>[CH3:7][O:8][C:9]([C:11]1[C:16]([NH:17][C:24](=[O:25])[C:23]2[CH:27]=[C:19]([Br:18])[CH:20]=[CH:21][C:22]=2[F:28])=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Pyridine (7.75 g, 98.0 mmol) was added at 0° C. under N2 to a solution of 3-amino-pyrazine-2-carboxylic acid methyl ester 101 (1.5 g, 9.80 mmol) and 5-bromo-2-fluorobenzoylchloride (9.45 g, 49.0 mmol) in CH2Cl2. The reaction mixture was warmed at 40° C. for 4 h, then cooled down at room temperature. The reaction mixture was quenched with 20 mL of ethanol, evaporated, partitioned between CH2Cl2 and 1N NaHCO3, dried (Na2SO4) and evaporated. The crude material was triturated in EtOH, filtered, washed with EtOH and ether to give 2.6 g of 3-(5-bromo-2-fluorobenzoyl-amino)pyrazine-2-carboxylic acid methyl ester 102 as a white powder (LCMS analysis).

Aufarbeitung

temperaturecooled down at room temperature
customThe reaction mixture was quenched with 20 mL of ethanol
customevaporated
custompartitioned between CH2Cl2 and 1N NaHCO3
dry with materialdried (Na2SO4)
customevaporated
customThe crude material was triturated in EtOH
filtrationfiltered
washwashed with EtOH and ether

Quellen und Nachweise

ORD-Eintrag: ord-0dbe4e01e51f4585b612c989d975e450
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09290502B2

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