Réaction #166729

Équation de réaction

(S)-tert-Butyl 2-(4-chlorophenyl)-3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)propyl(isopropyl)carbamate

TFA

dihydrochloride

→

(S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one

Rendement 40.0%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction was concentrated to dryness
2. 2
   workup.DISSOLUTIONThe crude residue was dissolved in minimal DCM
3. 3
   workup.ADDITIONadded dropwise to a stirring solution of 1M HCl in ether (10 mL)
4. 4
   FiltrationThe solid product was then filtered
5. 5
   Lavagewashed with ether
6. 6
   Autredried

Mode opératoire

(S)-tert-Butyl 2-(4-chlorophenyl)-3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)propyl(isopropyl)carbamate (0.003 g, 0.0050 mmol) was placed in DCM (2 mL) at room temperature. TFA (0.4 mL) was then added, and the reaction was stirred for 1 hour. The reaction was concentrated to dryness. The crude residue was dissolved in minimal DCM and added dropwise to a stirring solution of 1M HCl in ether (10 mL). The solid product was then filtered, washed with ether, and dried to give (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.001 g, 40% yield) as the dihydrochloride salt. MS ESI (+) m/z 503 detected.

Source