【结 构 式】 |
【分子编号】35940 【品名】2-([4-(2-benzoyl-4-chlorophenyl)-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-4H-1,2,4-triazol-3-yl]methyl)-1H-isoindole-1,3(2H)-dione 【CA登记号】 |
【 分 子 式 】C33H20ClN5O5 【 分 子 量 】602.0052 【元素组成】C 65.84% H 3.35% Cl 5.89% N 11.63% O 13.29% |
合成路线1
该中间体在本合成路线中的序号:(VII)The reaction of 2-amino-5-chlorobenzophenone (I) with formic acid gives 2-formylamino-5-chlorobenzophenone (II), which by cyclization with hydrazine in ethanol is converted into 3-amino-6-chloro-4-hydroxy-4-phenyl-3,4-dihydroquinazoline (III). The reaction of (III) with formic acid in acetic anhydride - acetic acid yields 5-chloro-2-(4H-1,2,4-triazol-4-yl)benzophenone (IV), which by reaction with formaldehyde in refluxing xylene affords 5-chloro-2-[3,5-bis(hydroxymethyl)-4H-1,2,4-triazol-4-yl]benzophenone (V). The reaction of (V) with phthalimide (VI), triethylphosphine and diethyl azodicarboxylate in THF gives 5-chloro-2-[3,5-bis(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone (VII), which is cyclized with hydrazine in hot ethanol to 8-chloro-1-(aminomethyl)-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine (VIII). Finally, this compound is methylated with formaldehyde and sodium cyanoborohydride in acetonitrile - acetic acid.
【1】 Gall, M.; Hester, J.B.; US 3947466 . |
【2】 Castaner, J.; Pento, J.T.; Blancafort, P.; Serradell, M.N.; Adinazolam. Drugs Fut 1983, 8, 2, 87. |
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) | 10279 | (2-Amino-5-chlorophenyl)(phenyl)methanone; 2-Amino-5-chlorobenzophenone | 719-59-5 | C13H10ClNO | 详情 | 详情 |
(II) | 35936 | 2-benzoyl-4-chlorophenylformamide | C14H10ClNO2 | 详情 | 详情 | |
(III) | 35937 | 3-amino-6-chloro-4-phenyl-3,4-dihydro-4-quinazolinol | C14H12ClN3O | 详情 | 详情 | |
(IV) | 35938 | [5-chloro-2-(4H-1,2,4-triazol-4-yl)phenyl](phenyl)methanone | C15H10ClN3O | 详情 | 详情 | |
(V) | 35939 | [2-[3,5-bis(hydroxymethyl)-4H-1,2,4-triazol-4-yl]-5-chlorophenyl](phenyl)methanone | C17H14ClN3O3 | 详情 | 详情 | |
(VI) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
(VII) | 35940 | 2-([4-(2-benzoyl-4-chlorophenyl)-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-4H-1,2,4-triazol-3-yl]methyl)-1H-isoindole-1,3(2H)-dione | C33H20ClN5O5 | 详情 | 详情 | |
(VIII) | 35941 | (8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methylamine; (8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine | C17H14ClN5 | 详情 | 详情 |