Reacción #2439942

ord-342c75a352d040968464bd96a26eccbc

Ecuación de reacción

CCn1nc(C)cc1C(=O)Nc1cccc(C(=O)c2ccc3c(c2)C(=CO)C(=O)N3)c1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide
C1CCOC1
THF
COc1ccc(N)cc1O
5-amino-2-methoxyphenol
CCn1nc(C)cc1C(=O)Nc1cccc(C(=O)c2ccc3c(c2)C(=CNc2ccc(C)c(O)c2)C(=O)N3)c1
title compound
Rendimiento 67.0%
CCn1nc(C)cc1C(=O)Nc1cccc(C(=O)c2ccc3c(c2)C(=CNc2ccc(C)c(O)c2)C(=O)N3)c1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (3-{3-[(3-hydroxy-4-methyl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-5-carbonyl}-phenyl)-amide
Rendimiento 67.0%

Disolventes

Condiciones de reacción

Temperatura
65°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroA small screw cap test tube
  2. 2
    TemperaturaSubsequently, the reaction mixture was cooled to room temperature
  3. 3
    OtroThe solid precipitate that formed

Procedimiento

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (as prepared in Example 1, 30 mg, 0.072 mmol) and THF (1 mL). To the resulting solution was added 5-amino-2-methoxyphenol (13.3 mg, 0.1082 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture. The solid precipitate that formed was washed with ˜1 mL of i-prOH yielding 67% (25 g, 0.048 mmol) of the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07749530B2uspto-grants-2010_07