Réaction #792165

ord-dd81812787634d6db6d545956d7029d3

Équation de réaction

Cc1cc(Cl)cc2c(=O)oc(-c3cc(Cl)nn3-c3ncccc3Cl)nc12
benzoxazinone
Cc1cc(Cl)cc2c(=O)oc(-c3cc(Cl)nn3-c3ncccc3Cl)nc12
6-Chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one
CN
methylamine
CNC(=O)c1cc(Cl)cc(C)c1NC(=O)c1cc(Cl)nn1-c1ncccc1Cl
title compound
CNC(=O)c1cc(Cl)cc(C)c1NC(=O)c1cc(Cl)nn1-c1ncccc1Cl
3-Chloro-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

Conditions de réaction

Température
60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurecooled to room temperature
  2. 2
    AutreThe tetrahydrofuran solvent was evaporated under reduced pressure
  3. 3
    Autrethe residual solid was purified by chromatography on silica gel

Mode opératoire

To a solution of the benzoxazinone product of Example 8, Step E (6.32 g, 15.47 mmol) in tetrahydrofuran (50 mL) was added methylamine (2.0 M solution in THF, 38 mL, 77.38 mmol), and the reaction mixture was heated to 60° C., stirred for 1 hour and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was purified by chromatography on silica gel to afford the title compound, a compound of the present invention, as a white solid (4.57 g) melting at 225-226° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09173400B2uspto-grants-2015_11