تفاعل #1509621

معادلة التفاعل

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

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر