Réaction #619171

Équation de réaction

DIEA

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

piperazine sulfonic acid dimethylamide hydrochloride

HBTU

→

desired compound

Rendement 67.1%

4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazine-1-sulfonic acid dimethylamide

Rendement 67.1%

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadded to a 10 mL reaction flask
2. 2
   Autrequenched with saturated aqueous NH4Cl (5 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 (10% EtOAc and 1% MeOH in CH2Cl2)

Mode opératoire

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (53 mg, 0.15 mmol), piperazine sulfonic acid dimethylamide hydrochloride (44 mg, 0.19 mmol), and HBTU (74 mg, 0.19 mmol) were weighed out and added to a 10 mL reaction flask. DMF (1.5 mL) and DIEA (65 μL, 0.38 mmol) were added. The reaction was stirred under nitrogen at ambient temperature overnight. The reaction was diluted with EtOAc (5 mL) and quenched with saturated aqueous NH4Cl (5 mL). After separation and extraction with EtOAc (2×5 mL) the combined organic portions were dried over MgSO4. Purification with silica gel (10% EtOAc and 1% MeOH in CH2Cl2) afforded 53 mg (67%) of the desired compound.

Source