Réaction #619170

Équation de réaction

DIEA

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

piperazine carboxylic acid tert-butyl ester

HBTU

→

desired compound

Rendement 72.0%

4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Rendement 72.0%

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 and 10% EtOAc in CH2Cl2

Mode opératoire

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (176 mg, 0.50 mmol), piperazine carboxylic acid tert-butyl ester (140 mg, 0.75 mmol), and HBTU (285 mg, 0.75 mmol) were weighed out and added to a 25 mL reaction flask. DMF (5 mL) and DIEA (175 μL, 1.0 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 and 10% EtOAc in CH2Cl2 afforded 187 mg (72%) of the desired compound.

Source