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Befunolol hydrochloride, BFE-60, Glauconex, Betaclar, Benfuran, Bentos

盐酸氧茚心安 苯呋洛尔 Chemical Name: 1-[7-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-2-benzofuranyl]ethanone hydrochloride; 7-[2-Hydroxy-3-(isopropylamino)propoxy]-2-benzofuranyl methyl ketone hydrochloride; 2-Acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran hydrochloride
CAS No. 39543-79-8, 39552-01-7 (free base)
项目整合开发状态: Launched-1984
项目研究机构: Kaken (Originator), Alcon (Licensee), Angelini (Licensee), Novartis (Licensee)
合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.
📌 参考资料/链接:
参考文献标题:2-Substittuted-(2-hydroxy-3-lower alkalinopropoxy)benzofurans
文献作者:Ito,K.; Ikemoto,M.; Kimura,K.; Nakanishi,T.(Kaken Pharmaceutical Co.,Ltd.)
参考来源:DE 2223184; FR 2137901; JP 7242747; US 3853923

📄 详细内容


合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.

参考文献标题:Befunolol
文献作者:Castar,J.; Blancafort,P.; Weetman,D.F.; Serradell,M.N.
参考来源:Drugs Fut 1981,6(10),601


合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.

参考文献标题:
文献作者:Ito,K.; Ikemoto,M.; Kimura,K.; Nakanishi,T.
参考来源:JP 7443960


合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.

参考文献标题:
文献作者:Ito,K.; Ikemoto,M.; Kimura,K.; Uchida,K.; Nakanishi,T.
参考来源:JP 7441358


合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.

参考文献标题:
文献作者:Ito,K.; Ikemoto,M.; Kimura,K.; Uchida,K.; Nakanishi,T.
参考来源:JP 7443961


合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.

参考文献标题:
文献作者:Ito,K.; Ikemoto,M.; Kimura,K.; Uchida,K.; Nakanishi,T.
参考来源:JP 7442664


合成路线:Compound can be prepared in several different ways:1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II),which is then condensed with isopropylamine (B) in refluxing ethanol.2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube.3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol,followed by hydrolysis of the reduced product with HCl in ethanol.4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V),which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol.5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH.6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.
参考文献标题:
文献作者:Ito,K.; Ikemoto,M.; Kimura,K.; Uchida,K.; Nakanishi,T.
参考来源:JP 7436664


产品链接: CAS No. 39543-79-8››

产品链接: CAS No.39552-01-7››