Reaction #619171

Reaction equation

DIEA

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

piperazine sulfonic acid dimethylamide hydrochloride

HBTU

→

desired compound

Yield 67.1%

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

Yield 67.1%

Solvents

DMF

EtOAc

Conditions

Workup

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

Procedure

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