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2
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Ng R.A., Guan J., Alford Jr. V.C., Lanter J.C., Allan G.F., Sbriscia T., Linton O., Lundeen S.G., and Sui Z. Bioorg. Med. Chem. Lett. (2007) 784
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Ng, R.A.1
Guan, J.2
Alford Jr., V.C.3
Lanter, J.C.4
Allan, G.F.5
Sbriscia, T.6
Linton, O.7
Lundeen, S.G.8
Sui, Z.9
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3
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33846663836
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Ng R.A., Guan J., Alford Jr. V.C., Lanter J.C., Allan G.F., Sbriscia T., Lundeen S.G., and Sui Z. Bioorg. Med. Chem. Lett. (2007) 955
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Lanter, J.C.4
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Sbriscia, T.6
Lundeen, S.G.7
Sui, Z.8
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4
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33847176936
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Ng R.A., Lanter J.C., Alford Jr. V.C., Allan G.F., Sbriscia T., Lundeen S.G., and Sui Z. Bioorg. Med. Chem. Lett. (2007) 1784
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Ng, R.A.1
Lanter, J.C.2
Alford Jr., V.C.3
Allan, G.F.4
Sbriscia, T.5
Lundeen, S.G.6
Sui, Z.7
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5
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-
47549091563
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Ng, R.; Sui, Z.; Guan, J.; Lanter, J. C.; Alford, V. C., Jr. Novel Benzimidazole Derivatives Useful As Selective Androgen Receptor Modulators (SARMS). WO 2006/039243 A1, 2006.
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Ng, R.; Sui, Z.; Guan, J.; Lanter, J. C.; Alford, V. C., Jr. Novel Benzimidazole Derivatives Useful As Selective Androgen Receptor Modulators (SARMS). WO 2006/039243 A1, 2006.
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6
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47549100620
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Liu, Z.; Milburn, C.; Page, D.; Walpole, C.; Yang, H. Benzimidazole Derivatives, Compositions Containing Them, Preparation Thereof And Uses Thereof. WO 2005/030762 A1, 2006.
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Liu, Z.; Milburn, C.; Page, D.; Walpole, C.; Yang, H. Benzimidazole Derivatives, Compositions Containing Them, Preparation Thereof And Uses Thereof. WO 2005/030762 A1, 2006.
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7
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47549097205
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Anderskewitz, R.; Martyres, D.; Dollinger, H.; Pouzet, P.; Birke, F.; Bouyssou, T. Haloalkyl- and Piperidine-Substituted Benzimidazole-Derivatives. WO 2005/019203 A1, 2005.
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9
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47549115642
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3 has not been previously employed in the synthesis of 2-trifluoroethylbenzimidazoles, this reagent has been successfully used to prepare non-fluorinated benzimidazoles by cyclodehydration. For example:
-
3 has not been previously employed in the synthesis of 2-trifluoroethylbenzimidazoles, this reagent has been successfully used to prepare non-fluorinated benzimidazoles by cyclodehydration. For example:. Kurasawa Y., Shimabukuro S., Okamoto Y., and Takeda A. Heterocycles 23 (1985) 65
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(1985)
Heterocycles
, vol.23
, pp. 65
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Kurasawa, Y.1
Shimabukuro, S.2
Okamoto, Y.3
Takeda, A.4
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13
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0037152308
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Ramig K., Englander M., Kallashi F., Livchits L., and Zhou J. Tetrahedron Lett. 43 (2002) 7731
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 7731
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Ramig, K.1
Englander, M.2
Kallashi, F.3
Livchits, L.4
Zhou, J.5
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19
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47549104125
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note
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Consistent with this is our observation that compound 11, which cannot eliminate HF, converts cleanly to 12 under acidic conditions. No evidence for loss of the trifluoromethyl group was observed {A figure is presented}.
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-
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20
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0001385309
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Hydrolysis of perfluorinated alkenes has been observed under acidic and basic conditions. For example:
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Hydrolysis of perfluorinated alkenes has been observed under acidic and basic conditions. For example:. England D.C. J. Org. Chem. 46 (1981) 147
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(1981)
J. Org. Chem.
, vol.46
, pp. 147
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England, D.C.1
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22
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0038754759
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Protonation of the benzimidazole nitrogen is likely under acidic conditions and may favor the decarboxylation event. Consistent with this, indole-2-acetic acids are stable and can be prepared by hydrolysis of the corresponding esters. For example:
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Protonation of the benzimidazole nitrogen is likely under acidic conditions and may favor the decarboxylation event. Consistent with this, indole-2-acetic acids are stable and can be prepared by hydrolysis of the corresponding esters. For example:. Weber D., Berger C., Eickelmann P., Antel J., and Kessler H. J. Med. Chem. 46 (2003) 1918
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(2003)
J. Med. Chem.
, vol.46
, pp. 1918
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Weber, D.1
Berger, C.2
Eickelmann, P.3
Antel, J.4
Kessler, H.5
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24
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47549103943
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note
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All 2-trifluoroethylbenzimidazoles listed in Table 2 are transformed to the corresponding 2-methylbenzimidazoles when heated in AcOH at 100 °C (observed by LC/MS).
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