Reacción #603701

ord-2476aaafa714499f8647fc3a2d8fb7c3

Ecuación de reacción

Cc1cc(Cl)cc2c(=O)oc(-c3cc(Br)nn3-c3ncccc3Cl)nc12
benzoxazine
Cc1cc(Cl)cc2c(=O)oc(-c3cc(Br)nn3-c3ncccc3Cl)nc12
2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-benzoxazin-4-one
CC(C)N
isopropylamine
Cc1cc(Cl)cc(C(=O)NC(C)C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl
title compound
Cc1cc(Cl)cc(C(=O)NC(C)C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl
3-Bromo-N-[4-chloro-2-methyl-6-[[(1-methylethyl)amino]-carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

Disolventes

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled to room temperature
  2. 2
    OtroThe tetrahydrofuran solvent was evaporated under reduced pressure
  3. 3
    Otrothe residual solid was triturated with ether
  4. 4
    Filtraciónfiltered
  5. 5
    Otrodried

Procedimiento

To a solution of the benzoxazine product of Step E (0.20 g, 0.44 mmol) in tetrahydrofuran was added isopropylamine (0.122 mL, 1.42 mmol), and the reaction mixture was heated to 60° C. for 90 minutes and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was triturated with ether, filtered, and dried to afford the title compound, a compound of the present invention, as a solid (150 mg), m.p. 159-161° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09113630B2uspto-grants-2015_08