Reaction #619180

Reaction equation

DIEA

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

1-morpholin-4-yl-2-piperazin-1-yl-ethanone

HBTU

→

desired compound

Yield 31.0%

1,1-Dicyclohexyl-3-{5-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-thiazol-2-yl}-urea

Yield 31.0%

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 chromatography (10% EtOAc and 1% MeOH in CH2Cl2)

Procedure

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (53 mg, 0.15 mmol), 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (42 mg, 0.19 mmol), and HBTU (71 mg, 0.19 mmol) were weighed out and added to a 25 mL reaction flask. DMF (2 mL) and DIEA (65 μL, 0.37 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 chromatography (10% EtOAc and 1% MeOH in CH2Cl2) afforded 17 mg (31%) of the desired compound.

Source