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

【结 构 式】

【分子编号】12959

【品名】7-Chloro-2-(2-cyclohexylethyl)-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

【CA登记号】

【 分 子 式 】C13H15ClN4O3S

【 分 子 量 】342.80596

【元素组成】C 45.55% H 4.41% Cl 10.34% N 16.34% O 14% S 9.35%

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:(VII)

This compound can be obtained by two related ways: 1) The cyclization of 3-cyclohexylpropionitrile (I) with thiosemicarbazide (II) by means of trifluoroacetic acid gives 5-(2-cyclohexylethyl)-1,3,4-thiadiazol-2-amino (III), which is submitted to a new cyclization process with bis(2,4,6-trichlorophenyl)malonate (IV) in refluxing xylene yielding 2-(2-cyclohexylethyl)-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (V) (1-3). The nitration of (V) with fuming nitric acid in acetic acid affords the corresponding 7-hydroxy-6-nitro derivative (VI), which is treated with POCl3 and tripropylamine to afford the 7-chloro-6-nitro derivative (VII). The reaction of (VII) with concentrated aqueous NH4OH in ethanol gives the corresponding 7-amino-6-nitro compound (VIII), which is reduced with Sn-HCl in dioxane-water to afford the 6,7-diamino derivative (IX). Finally, this compound is dissolved in aqueous HCl and treated with NaNO2. 2) The cyclization of 3-cyclohexylpropionic acid (X) with thiosemicarbazide (II) by means of hot H2SO4 gives the thiadiazole (III), which is cyclized again with malonic acid (XI) by means of POCl3 in hot toluene to afford the previously obtained thiadiazolopyrimidine (V).

1 Isoda, S.; Aibara, S.; Miwa, T.; Fujiwara, H.; Yokohama, S.; Matsumoto, H. (Daiichi Pharmaceutical Co., Ltd.); Tricyclic triazolopyrimidine derivatives. AU 9052298; EP 0279298; JP 1989000086; JP 1989006264; US 4898943 .
2 Narabayashi, Y. (Daiichi Pharmaceutical Co., Ltd.); Agents for treatment of gastrointestinal diseases. JP 1990138216 .
3 Aihara, S. (Daiichi Pharmaceutical Co., Ltd.); Antiallergic and antiinflammatory agents. JP 1990138215 .
4 Yokohama, S.; Miwa, T.; Aibara, S.; Fujiwara, H.; Matsumoto, H.; Nakayama, K.; Iwamoto, T.; Mori, M.; Moroi, R.; Tsukada, W.; Isoda, S.; Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. II. 6-Alkyl- and 6-cycloalkylalkyl derivatives. Chem Pharm Bull 1992, 40, 9, 2391-8.
5 Rabasseda, X.; Castaner, J.; Mealy, N.; DS-4574. Drugs Fut 1994, 19, 10, 901.
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) 12953 3-Cyclohexylpropanenitrile C9H15N 详情 详情
(II) 12954 1-Hydrazinecarbothioamide; Thiosemicarbazide 79-19-6 CH5N3S 详情 详情
(III) 12955 5-(2-Cyclohexylethyl)-1,3,4-thiadiazol-2-ylamine; 5-(2-Cyclohexylethyl)-1,3,4-thiadiazol-2-amine C10H17N3S 详情 详情
(IV) 12956 bis(2,4,6-trichlorophenyl) malonate C15H6Cl6O4 详情 详情
(V) 12957 2-(2-Cyclohexylethyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one C13H17N3O2S 详情 详情
(VI) 12958 2-(2-Cyclohexylethyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one C13H16N4O4S 详情 详情
(VII) 12959 7-Chloro-2-(2-cyclohexylethyl)-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one C13H15ClN4O3S 详情 详情
(VIII) 12960 7-Amino-2-(2-cyclohexylethyl)-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one C13H17N5O3S 详情 详情
(IX) 12961 6,7-Diamino-2-(2-cyclohexylethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one C13H19N5OS 详情 详情
(X) 12962 3-Cyclohexylpropionic acid 701-97-3 C9H16O2 详情 详情
(XI) 12963 Malonic acid 141-82-2 C3H4O4 详情 详情
Extended Information