Hydrazinecarboxaldehyde → 9-bromopyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 707471

Reaktionsgleichung

Reaktionsgleichung von HRID 707471
[CH:1]([NH:3][NH2:4])=[O:2].[Br:5][C:6]1[CH:7]=[C:8]([C:17]#[N:18])[C:9]([NH:12]C(=O)OC)=[N:10][CH:11]=1.[CH3:19]N1CCCC1=O>>[Br:5][C:6]1[CH:11]=[N:10][C:9]2[NH:12][C:1](=[O:2])[N:3]3[N:4]=[CH:19][N:18]=[C:17]3[C:8]=2[CH:7]=1

Komponenten

4

Edukt 3

HCID 12229HydrazinecarboxaldehydeHCID 13387N-methyl-2-pyrrolidoneHCID 86705383Methyl 5-bromo-3-cyanopyridin-2-ylcarbamate

Produkt 1

HCID 1363380329-bromopyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneAusbeute 60 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Formyl hydrazine (60 mg, 1.0 mmol) was added to a solution of methyl 5-bromo-3-cyanopyridin-2-ylcarbamate (255 mg, 1.0 mmol) in 1-methylpyrrolidinone (5 mL) and the resulting mixture was stirred at 120° C. for 3 hours. The mixture was cooled to room temperature and poured into ice-water (20 mL). The resulting solid was separated by filtration, washed with water and hexanes and dried under vacuum to afford the title compound (160 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.70 (s, 1H), 8.80 (s, 1H), 13.00 (br s, 1H). LCMS (MH+, 266.3).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe resulting solid was separated by filtration
  3. washwashed with water and hexanes
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b62abec7192d48dfac506b6aa4ec280e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175010B2

Verknüpfte Notizen

Wird geladen…