Tilisolol: Difference between revisions

{{short description|Chemical compound}}

| verifiedrevid =

| = mixture

| drug_name =

| CAS_number_Ref = {{cascite|correct|??}}

| ChemSpiderID = 5275

| StdInChI = 1S/C17H24N2O3/c1-17(2,3)18-9-12(20)11-22-15-10-19(4)16(21)14-8-6-5-7-13(14)15/h5-8,10,12,18,20H,9,11H2,1-4H3

| StdInChIKey = TWVUMMQUXMYOOH-UHFFFAOYSA-N

'''Tilisolol''' ([[International Nonproprietary Name|INN]], trade name '''Selecal''') is a [[beta blocker]].

==Synthesis==

[[File:Tilisolol synthesis.svg|center|500px|thumb|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0089 Thieme] [https://www.chemdrug.com/article/8/3284/16419653.html ChemDrug] Synthesis:<ref>Serradell, MN; Blancafort, P.; Thorpe, PJ; Castaer, J.; N-696. Drugs Fut 1982, 7, 12, 889.</ref> Patent:<ref>Hideo Saitama Jp Fukushima, Yoshikuni Kawagoe Saitama Jp Suzuki, DE2631080 (1985 to Nisshin Flour Milling Co., Ltd., Tokio / Tokyo, Jp).</ref> Precursor:<ref>Lombardino, J. G. (October 1970). "Synthesis of 4‐hydroxy‐2‐methylisocarbostyril‐3‐carboxanilides". Journal of Heterocyclic Chemistry. 7 (5): 1057–1060. doi:10.1002/jhet.5570070509.</ref> Sino:<ref>Li Leilei, et al. CN102115459 (2011 to Dihon Pharmaceutical Group Co Ltd).</ref> HPLC:<ref>Yonezawa K, Sato K, Kobayashi A. High-performance liquid chromatography of a new beta-blocker, 4-[3-(tert.-butylamino)-2-hydroxypropoxy]-N-methylisocarbostyril hydrochloride, in plasma using fluorometric detection. J Chromatogr. 1985 Apr 12;339(1):219-22. doi: 10.1016/s0378-4347(00)84648-4. PMID: 2862154.</ref>]]

The methanolysis of Phthalic anhydride [85-44-9] (1) gives Methyl hydrogen phthalate [4376-18-5] (2). Schotten-Baumann amidation with Methyl sarcosinate [5473-12-1] (3) gives Methyl 2-[(2-methoxy-2-oxoethyl)-methylcarbamoyl]benzoate, PC11644670 (4). Intramolecular lactamization with sodium methoxide afforded Methyl 4-hydroxy-2-methyl-1-oxoisoquinoline-3-carboxylate, PC54684295 (5). In lye saponification followed by decarboxylation occurred to give 4-hydroxy-2-methylisoquinolin-1(2H)-one [30236-50-1] (6). Treatment with Epichlorhydrin [106-89-8] (7) in the presence of base led to 2-Methyl-4-[(oxiran-2-yl)methoxy]isoquinolin-1(2H)-one [62775-08-0] (8). Opening of the oxirane ring with tert-Butylamine [75-64-9] (9) completed the synthesis of Tilisolol (10).

== References ==

{{Reflist}}

[[Category:]]

[[Category:Amines]]

[[Category:Tert-butyl compounds]]