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【结 构 式】 
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【药物名称】S-18327 【化学名称】1-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]ethyl]-3-phenylimidazolidin-2-one 【CA登记号】200398-40-9 【 分 子 式 】C23H25FN4O2 【 分 子 量 】408.4797 |
【开发单位】Servier (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2A Antagonists, alpha1-Adrenoceptor Antagonists, Dopamine D4 Antagonists |
合成路线1
Condensation of phenyl isocyanate (I) with diethanolamine (II) produced 1,1-bis(2-hydroxyethyl)-3-phenylurea (III), which was converted into the bis(chloroethyl) derivative (IV) upon treatment with SOCl2. Cyclization of this compound at 140 C furnished imidazolinone (V). Finally, condensation of (V) with benzisoxazolylpiperidine (VI) in the presence of K2CO3 and KI in refluxing methyl isobuyl ketone yielded the title compound.
| 【1】 Audinot, V.; Millan, M.; Brocco, M.; Peglion, J.-L. (ADIR et Cie.); 3-(Piperid-4-yl)-1,2-benzisoxazole and 3-(piperazin-4-yl)-1,2-benzisoxazole cpds.. EP 0811622; FR 2749304; US 5780474 . |
| 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) | 11289 | 1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate | 103-71-9 | C7H5NO | 详情 | 详情 |
| (II) | 24273 | 2-[(2-hydroxyethyl)amino]-1-ethanol | 111-42-2 | C4H11NO2 | 详情 | 详情 |
| (III) | 36999 | N,N-bis(2-hydroxyethyl)-N'-phenylurea | C11H16N2O3 | 详情 | 详情 | |
| (IV) | 37000 | N,N-bis(2-chloroethyl)-N'-phenylurea | C11H14Cl2N2O | 详情 | 详情 | |
| (V) | 37001 | 1-(2-chloroethyl)-3-phenyl-2-imidazolidinone | C11H13ClN2O | 详情 | 详情 | |
| (VI) | 17910 | 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole | C12H13FN2O | 详情 | 详情 |