Pierce, Michael E. published the artcilePractical synthesis and regioselective alkylation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist, Application of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, the publication is Journal of Organic Chemistry (1993), 58(17), 4642-5, database is CAplus.
(Hydroxymethyl)[(tetrazolylbiphenyl)methyl]imidazole, DuP 532 (I), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes. One route, which is more practical for large-scale synthesis, required the preparation of Me 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (II, R = C2F5). This imidazole was synthesized in five steps from com. available 2-propyl-4(5)-(hydroxymethyl)imidazole in 32% overall yield. Alternate perfluoroalkylation methods of the iodoimidazole precursor II (R = iodo) are presented. II (R = C2F5) (III) is remarkably stable to basic conditions and is alkylated by 2-[N-(triphenylmethyl)tetrazol-5-yl]-4′-(bromomethyl)-1′,1′-biphenyl (IV), giving only the desired regioisomer. A comparison of the alkylation of the trisubstituted precursors and analogs to III with IV indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is SE2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole which alkylates as a neutral species (SE2′).
Journal of Organic Chemistry published new progress about 79047-41-9. 79047-41-9 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Alcohol, name is (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol, and the molecular formula is C8H13ClN2O, Application of (2-Butyl-4-chloro-1H-imidazol-5-yl)methanol.
Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem