Reaction #1509621

Reaction equation

EDC HOBt

2-amino-4-(3-carboxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester

1-hydroxybenzotriazole

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

2-amino-4-[3-(pyrimidin-2-ylcarbamoyl)-propyl]-imidazole-1-carboxylic acid tert-butyl ester

Solvents

DMF

Conditions

Workup

1. 1
   ConcentrationThe reaction was concentrated under reduced pressure
2. 2
   Otherthe residue partitioned between ethyl acetate (20 mL) and water (10 mL) The organic layer
3. 3
   Washwas successively washed with water (3×10 mL)
4. 4
   Dryinga 10% aqueous solution of citric acid (2×10 mL), sat. NaHCO3 (2×10 mL), and brine (10 mL) before being dried (Na2SO4)
5. 5
   Otherevaporated to dryness
6. 6
   OtherThe crude product was purified via flash column chromatography (2-10% MeOH/CH2Cl2)
7. 7
   Otherto afford the target compound

Procedure

General EDC/HOBt Procedure: 2-amino-4-(3-carboxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester 22 (100 mg, 0.371 mmol), 1-hydroxybenzotriazole (100 mg, 0.742 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (142 mg, 0.742 mmol) were dissolved in anhydrous DMF (3 mL). The appropriate amine coupling partner (1.48 mmol) was then added and the solution was stirred at ambient temperature until completion was evident by TLC analysis. The reaction was concentrated under reduced pressure and the residue partitioned between ethyl acetate (20 mL) and water (10 mL) The organic layer was successively washed with water (3×10 mL), a 10% aqueous solution of citric acid (2×10 mL), sat. NaHCO3 (2×10 mL), and brine (10 mL) before being dried (Na2SO4) and evaporated to dryness. The crude product was purified via flash column chromatography (2-10% MeOH/CH2Cl2) to afford the target compound.

Source