• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】15362

【品名】N-(4-cyanophenyl)acetamide

【CA登记号】35704-19-9

【 分 子 式 】C9H8N2O

【 分 子 量 】160.1754

【元素组成】C 67.49% H 5.03% N 17.49% O 9.99%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

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%.

1 Tidwell, R.R.; Geratz, J.D.; BBE. Drugs Fut 1992, 17, 5, 371.
2 Dann, O.; Volz, G.; Loewe, H.; Zeh, D.; Tidwell, R.R.; Geratz, J.D.; Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases. J Med Chem 1978, 21, 7, 613-23.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 15361 4-Aminobenzonitrile 873-74-5 C7H6N2 详情 详情
(II) 15362 N-(4-cyanophenyl)acetamide 35704-19-9 C9H8N2O 详情 详情
(III) 15363 4-amino-3-nitrobenzonitrile 6393-40-4 C7H5N3O2 详情 详情
(IV) 15364 4-amino-3-nitrobenzenecarboximidamide C7H8N4O2 详情 详情
(V) 15365 3,4-diaminobenzenecarboximidamide C7H10N4 详情 详情
(VI) 15366 fumaronitrile; (E)-2-butenedinitrile 17656-09-6 C4H2N2 详情 详情
(VII) 15367 diethyl (E)-2-butenediimidoate C8H14N2O2 详情 详情
Extended Information