Benzoyl chloride → Methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate

HRID 1802183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802183
C[C:2]1[CH:7]=[C:6](C)[CH:5]=[C:4]([CH3:9])[C:3]=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[C:19]([F:21])[C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1[NH2:26].C(Cl)(=O)C1C=CC=CC=1>N1C=CC=CC=1>[F:21][C:19]1[C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]2[N:15]([N:14]=[C:9]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=3)[N:26]=2)[CH:20]=1

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 866660181,2-Diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate

Produkt 1

HCID 67776717Methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylateAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1,2-diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate (1.719 g, 4.46 mmol) and benzoyl chloride (1.03 ml, 8.92 mmol) in pyridine (12 ml) is stirred for 20 hours at 100° C. The solvent is evaporated and the residue stirred for 2.5 hours with sat. aqueous ammoniumchloride solution while neutralizing to pH 6-7 with sat. aqueous sodium bicarbonate solution. The solid is collected by filtration, washed with water and dried affording methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (603 mg, 49.8%) as a light brown solid. Mp.: 162-8° C. MS: m/z=272.2 (M+H+).

Aufarbeitung

  1. customThe solvent is evaporated
  2. stirringthe residue stirred for 2.5 hours with sat. aqueous ammoniumchloride solution
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6d8b2ad8f8de4a489de97708bd04c9ff
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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