Реакция #1509621

Уравнение реакции

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

Растворители

DMF

Условия реакции

Обработка

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

Методика

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.

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