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

HRID 926111

Reaktionsgleichung

Reaktionsgleichung von HRID 926111
[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). The resulting mixture was stirred at 120° C. for 3 h. 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). [M+H]=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-b655ac79572347d6adb6b7d29dc6112e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284335B2

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