Reaktion #619180

Reaktionsgleichung

DIEA

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid

1-morpholin-4-yl-2-piperazin-1-yl-ethanone

HBTU

→

desired compound

Ausbeute 31.0%

1,1-Dicyclohexyl-3-{5-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-thiazol-2-yl}-urea

Ausbeute 31.0%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded to a 25 mL reaction flask
2. 2
   Sonstigequenched with saturated aqueous NH4Cl (10 mL)
3. 3
   SonstigeAfter separation and extraction with EtOAc (2×5 mL) the combined organic portions
4. 4
   Trocknenwere dried over MgSO4
5. 5
   SonstigePurification with silica gel chromatography (10% EtOAc and 1% MeOH in CH2Cl2)

Vorschrift

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (53 mg, 0.15 mmol), 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (42 mg, 0.19 mmol), and HBTU (71 mg, 0.19 mmol) were weighed out and added to a 25 mL reaction flask. DMF (2 mL) and DIEA (65 μL, 0.37 mmol) were added. The reaction was stirred under nitrogen at ambient temperature overnight. The reaction was diluted with EtOAc (10 mL) and quenched with saturated aqueous NH4Cl (10 mL). After separation and extraction with EtOAc (2×5 mL) the combined organic portions were dried over MgSO4. Purification with silica gel chromatography (10% EtOAc and 1% MeOH in CH2Cl2) afforded 17 mg (31%) of the desired compound.

Quelle