Réaction #2286330

Équation de réaction

(2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

(2-Cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

potassium acetate

acetic acid

water

→

2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo -1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile

Rendement 85.8%

2-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

Rendement 85.8%

Solvants

N,N-dimethylacetamide

acetonitrile

Conditions de réaction

Traitement

1. 1
   AutreThe solids which resulted
2. 2
   Filtrationwere collected by filtration
3. 3
   Lavagewashed with water (65 mL)
4. 4
   Autredried under vacuum
5. 5
   Autreto give an orange solid
6. 6
   Températureheated
7. 7
   Températureto reflux for 3 h
8. 8
   Températurecooled to room temperature
9. 9
   FiltrationThe resulting solids were then collected by filtration
10. 10
    Lavagewashed with acetonitrile (12 mL) and methyl tert-butyl ether (24 mL)
11. 11
    Autredried under vacuum

Mode opératoire

A solution of (2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (68) (6.5 g, 13.12 mmol) and potassium acetate (1.42 g, 14.43 mmol) in N,N-dimethylacetamide was heated to 120° C. for 2 h. At this time, the reaction was cooled to room temperature and was treated with glacial acetic acid (1.5 mL) and water (65 mL). The mixture was stirred at room temperature for 15 min. The solids which resulted were collected by filtration, washed with water (65 mL) and dried under vacuum to give an orange solid. The solid was suspended in acetonitrile (36 mL), heated to reflux for 3 h and then cooled to room temperature. The resulting solids were then collected by filtration, washed with acetonitrile (12 mL) and methyl tert-butyl ether (24 mL) and dried under vacuum to afford 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo -1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile (69) (5.06 g, 85.8%) as an orange solid; ES(+)-HRMS m/e calcd for C18H14Cl2N6O4 (M+H)+ 449.0527, found 449.0527. Exact Mass=448.0454; Molecular Weight=449.26.

Source