Reaktion #1752879

Reaktionsgleichung

4-thiophen-3-yl-phenylamine

EDCI

3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid

HOBT

→

3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(4-thiophen-3-yl-phenyl)-propionamide

Ausbeute 19.2%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas continued at room temperature overnight
2. 2
   Sonstigethe formed precipitate was collected
3. 3
   SonstigePurification by preparative HPLC

Vorschrift

DMAP (104 mg, 0.85 mmol) was added to 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid (167 mg, 0.47 mmol) in DMF (2 mL) followed by EDCI (90 mg, 0.47 mmol) and HOBT (63 mg, 0.47 mmol). After 2 minutes, 4-thiophen-3-yl-phenylamine (75 mg, 0.43 mmol) was added and stirring was continued at room temperature overnight. Cold water was added and the formed precipitate was collected. Purification by preparative HPLC afforded 42 mg (19.2% yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(4-thiophen-3-yl-phenyl)-propionamide. LC/MS [M+H]+: 512.06, 93.02%. 1H NMR (300 MHz, CDCl3): δ 9.6 (d, 1H), 7.85-7.5 (m, 5H), 7.46-7.34 (m, 4H), 7.34-7.26 (m, 2H), 4.09-3.9 (m, 2H), 3.82-3.64 (m, 4H), 3.58-3.52 (s, 1H), 3.5-3.44 (s, 1H), 3.42-3.32 (m, 1H), 3.3-3.18 (m, 1H).

Quelle