Реакция #2275766

Уравнение реакции

5-Isocyanato-benzo[1,3]dioxole

N-{[1-(4-amino-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide TFA salt

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title compound

N-({1-[4-(3-Benzo[1,3]dioxol-5-yl-ureido)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеquenched with saturated sodium bicarbonate
2. 2
   ДругоеThe reaction was then partitioned between DCM and water
3. 3
   ДругоеThe organic layer was separated
4. 4
   Экстракцияthe aqueous layer was extracted 3 times with a chloroform/IPA “cocktail” (˜3:1
5. 5
   СушкаThe combined organic layers were dried over anhydrous Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   Другоеto give the crude product, which
9. 9
   Другоеwas then purified by a CombiFlash® system

Методика

5-Isocyanato-benzo[1,3]dioxole (Aldrich, 50 mg, 0.302 mmol) was added into a solution of N-{[1-(4-amino-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide TFA salt (150 mg, 0.302 mmol) and TEA (127 μL, 0.906 mmol) in DMF (3 mL) at room temperature. The reaction was stirred overnight and quenched with saturated sodium bicarbonate. The reaction was then partitioned between DCM and water. The organic layer was separated and the aqueous layer was extracted 3 times with a chloroform/IPA “cocktail” (˜3:1, v/v). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as white solid.

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