Reaktion #619170

Reaktionsgleichung

DIEA

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

piperazine carboxylic acid tert-butyl ester

HBTU

→

desired compound

Ausbeute 72.0%

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

Ausbeute 72.0%

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 and 10% EtOAc in CH2Cl2

Vorschrift

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.

Quelle