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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

용매

DMF

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후처리

1. 1
   기타quenched with saturated sodium bicarbonate
2. 2
   기타The reaction was then partitioned between DCM and water
3. 3
   기타The organic layer was separated
4. 4
   추출the aqueous layer was extracted 3 times with a chloroform/IPA “cocktail” (˜3:1
5. 5
   건조The combined organic layers were dried over anhydrous Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to give the crude product, which
9. 9
   기타was then purified by a CombiFlash® system

실험 절차

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.

출처