Reacción #170817

Ecuación de reacción

N-ethyl-N-isopropylpropan-2-amine

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride

1H-benzo[d][1,2,3]triazol-1-ol

→

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(4-isopropylphenethyl)piperidine-4-carboxamide

Disolventes

DCM

DCM

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic layer was washed with 1N HCl, saturated sodium bicarbonate solution, and finally saturated sodium chloride solution
2. 2
   SecadoThe organic layer was dried over magnesium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe crude material purified

Procedimiento

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (72.5 mg, 0.378 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (51.1 mg, 0.378 mmol) were dissolved in 2.0 mL of DCM and stirred for 10 minutes before the addition of a 2-(4-isopropylphenyl)ethanamine, HCl (75 mg, 0.378 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.132 mL, 0.756 mmol) as a 1.0 mL DCM solution. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with 1N HCl, saturated sodium bicarbonate solution, and finally saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material purified using silica gel chromatography 0-60% ethyl acetate/hexanes. (Yield: 50 mg, white solid) 1H-NMR (500 MHz, DMSO-d6) 7.88, 7.62, 7.55, 7.34, 7.22, 7.18-7.06, 6.71, 5.49, 4.40, 3.97, 3.24, 3.13-2.73, 2.66, 2.40-2.29, 1.79-1.23, 1.16

Fuente