BBE-药物合成数据库

【药物名称】BBE

化学结构式(Chemical Structure):

参考文献No.	168957
标题:	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases
作者:	Tidwell, R.R.; Geratz, J.D.; Dann, O.; Volz, G.; Zeh, D.; Loewe, H.
来源:	J Med Chem 1978,21(7),613-23

合成路线图解说明: The synthesis of BBE was accomplished using a modified version of a published procedure, as outlined in Scheme 17960101a: Following acetylation (II) of the amine group, 4-aminobenzonitrile (I) was nitrated with potassium nitrate and the acetyl group removed with boiling sulfuric acid to give the mono-nitro product (III). The nitrile was converted to the corresponding amidine in two steps via the Pinner amidine synthesis (1, 2) to give 4-amino-3-nitrobenzamidine (IV). Reduction of the nitro group with 10% Pd-C in a Parr hydrogenator afforded a 60% yield (from compound I) of 3,4-diaminobenzamidine (V). The di-imidate (VII) of fumaronitrile (VI) was prepared by reacting the dinitrile in freshly distilled ethanol with dry HCl gas at 10 C. The di-imidate (VII) was reacted immediately with a 1/2 molar equivalent of 3,4-diaminobenzamidine in refluxing glacial acetic acid. The final product was isolated by trituration with ethyl acetate and filtration. BBE was purified by two recrystallizations from 4% HCl. The yield of the purified product was 15%.

参考文献No.	172950
标题:	BBE
作者:	Tidwell, R.R.; Geratz, J.D.
来源:	Drugs Fut 1992,17(5),371

合成路线图解说明: The synthesis of BBE was accomplished using a modified version of a published procedure, as outlined in Scheme 17960101a: Following acetylation (II) of the amine group, 4-aminobenzonitrile (I) was nitrated with potassium nitrate and the acetyl group removed with boiling sulfuric acid to give the mono-nitro product (III). The nitrile was converted to the corresponding amidine in two steps via the Pinner amidine synthesis (1, 2) to give 4-amino-3-nitrobenzamidine (IV). Reduction of the nitro group with 10% Pd-C in a Parr hydrogenator afforded a 60% yield (from compound I) of 3,4-diaminobenzamidine (V). The di-imidate (VII) of fumaronitrile (VI) was prepared by reacting the dinitrile in freshly distilled ethanol with dry HCl gas at 10 C. The di-imidate (VII) was reacted immediately with a 1/2 molar equivalent of 3,4-diaminobenzamidine in refluxing glacial acetic acid. The final product was isolated by trituration with ethyl acetate and filtration. BBE was purified by two recrystallizations from 4% HCl. The yield of the purified product was 15%.