Methods of synthesizing cyclic nitro compounds
View Patent ↗The present invention provides cyclic nitro compounds, pharmaceutical compositions of cyclic nitro compounds and methods of using cyclic nitro compounds and/or pharmaceutical compositions thereof to treat or prevent diseases or disorders characterized by abnormal cell proliferation, such as cancer, inflammation, cardiovascular disease and autoimmune disease.
1. A method of synthesizing N-(succinyl)-3,3-dinitroazetidine, comprising:
reacting tert-butyl-3,3-dinitroazetidine (“t-BuDNAZ”), an acid catalyst, and succinyl chloride.
2. The method of claim 1 , further comprising filtering, washing, and drying a reaction product of t-BuDNAZ, the acid catalyst, and succinyl chloride to produce N-(succinyl)-3,3-dinitroazetidine.
3. A method of synthesizing N-(fumaryl)-3,3-dinitroazetidine, comprising:
reacting tert-butyl-3,3-dinitroazetidine (“t-BuDNAZ”), an acid catalyst, and fumaryl chloride.
4. The method of claim 3 , further comprising filtering, washing, and drying a reaction product of t-BuDNAZ, the acid catalyst, and fumaryl chloride to produce N-(fumaryl)-3,3-dinitroazetidine.
5. A method of synthesizing N-(trifluoroacetyl)-3,3-dinitroazetidine, comprising:
reacting tert-butyl-3,3-dinitroazetidine (“t-BuDNAZ”), an acid catalyst, and trifluoroacetic anhydride.
6. The method of claim 1 , wherein reacting tent-butyl-3,3-dinitroazetidine (“t-BuDNAZ”), an acid catalyst, and succinyl chloride comprises reacting t-BuDNAZ, boron trifluoride etherate, and succinyl chloride.
7. The method of claim 2 , wherein filtering, washing, and drying a reaction product of t-BuDNAZ, the acid catalyst, and succinyl chloride to produce N-(succinyl)-3,3-dinitroazetidine comprises washing the reaction product of t-BuDNAZ, the acid catalyst, and succinyl chloride with dichloromethane.
8. The method of claim 3 , wherein reacting tert-butyl-3,3-dinitroazetidine (“t-BuDNAZ”), an acid catalyst, and fumaryl chloride comprises reacting t-BuDNAZ, boron trifluoride etherate, and fumaryl chloride.
9. The method of claim 4 , wherein filtering, washing, and drying a reaction product of t-BuDNAZ, the acid catalyst, and fumaryl chloride to produce N-(fumaryl)-3,3-dinitroazetidine comprises washing the reaction product of t-BuDNAZ, the acid catalyst, and fumaryl chloride with water.
10. The method of claim 5 , wherein reacting tert-butyl-3,3-dinitroazetidine (“t-BuDNAZ”), an acid catalyst, and trifluoroacetic anhydride comprises reacting t-BuDNAZ, boron trifluoride etherate, and trifluoroacetic anhydride.
11. The method of claim 5 , further comprising washing a reaction product of t-BuDNAZ, the acid catalyst, and trifluoroacetic anhydride with water.