Réaction #619180

Équation de réaction

DIEA

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

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

HBTU

→

desired compound

Rendement 31.0%

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

Rendement 31.0%

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source