Reaction #619170

Reaction equation

DIEA

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

piperazine carboxylic acid tert-butyl ester

HBTU

→

desired compound

Yield 72.0%

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

Yield 72.0%

Solvents

DMF

EtOAc

Conditions

Workup

1. 1
   workup.ADDITIONadded to a 25 mL reaction flask
2. 2
   Otherquenched with saturated aqueous NH4Cl (10 mL)
3. 3
   OtherAfter separation and extraction with EtOAc (2×5 mL) the combined organic portions
4. 4
   Dryingwere dried over MgSO4
5. 5
   OtherPurification with silica gel and 10% EtOAc in CH2Cl2

Procedure

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