Réaction #166763

Équation de réaction

(S)-3-(tert-Butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid

(S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid

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

HOBt H2O

triethylamine

5-(4-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

→

(S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

Rendement 40.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 1N HCl, 10% K2CO3 and brine
2. 2
   SéchageAfter drying with MgSO4 and concentration
3. 3
   Autrethe resulting residue was purified by chromatography (SP4, 12+M, water/ACN 80/20→0/100, 20CV)

Mode opératoire

(S)-3-(tert-Butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (87 mg, 0.25 mmol, see Example H), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (65 mg, 0.34 mmol), HOBt-H2O (52 mg, 0.34 mmol) and triethylamine (51 mg, 0.51 mmol) were added to 5-(4-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (50 mg, 0.17 mmol) in DCM (10 mL). The reaction was stirred for 18 hours. The reaction was then diluted with DCM (50 mL) and washed with 1N HCl, 10% K2CO3 and brine. After drying with MgSO4 and concentration, the resulting residue was purified by chromatography (SP4, 12+M, water/ACN 80/20→0/100, 20CV) to yield (S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (42 mg, 40% yield) as a solid.

Source