【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% |
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 |