Reacción #2439940

ord-465475ae4d384fd19861e6a1a0519745

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
CN1CCN(c2ccc(N)cc2)CC1
4-(4-methyl-piperazin-1-yl)-phenylamine
CCn1nc(C)cc1C(=O)Nc1cccc(C(=O)c2ccc3c(c2)C(=CNc2ccc(N4CCN(C)CC4)cc2)C(=O)N3)c1
title compound
Rendimiento 57.0%
CCn1nc(C)cc1C(=O)Nc1cccc(C(=O)c2ccc3c(c2)C(=CNc2ccc(N4CCN(C)CC4)cc2)C(=O)N3)c1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide
Rendimiento 57.0%

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
    ConcentraciónThe reaction mixture was concentrated in vacuo
  4. 4
    Otropurified via flash silica gel chromatography (5% MeOH/95% CHCl3)

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 4-(4-methyl-piperazin-1-yl)-phenylamine (20.7 mg, 0.1082 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. The reaction mixture was concentrated in vacuo and purified via flash silica gel chromatography (5% MeOH/95% CHCl3) providing the title compound in 57% yield (24 mg, 0.0407 mmol).

Fuente

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