【结 构 式】 |
【药物名称】Modafinil, CRL-40476, Modavigil, Modasomil, Vigil, Alertec, Provigil, Modiodal 【化学名称】2-[(Diphenylmethyl)sulfinyl]acetamide 【CA登记号】68693-11-8 【 分 子 式 】C15H15NO2S 【 分 子 量 】273.3563 |
【开发单位】Azwell (Orphan Drug), Lafon (Originator), Novartis (Marketer), Azwell (Licensee), Cephalon (Licensee), Dompè(Licensee), Draxis Health (Licensee), Shire Pharmaceuticals (Licensee) 【药理作用】Alzheimer's Dementia, Treatment of , Antidepressants, Antinarcoleptic Drugs, Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, Cognition Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, Neurologic Drugs (Miscellaneous), PSYCHOPHARMACOLOGIC DRUGS, Sleep Disorders, Treatment of, alpha1-Adrenoceptor Agonists |
合成路线1
This compound can be obtained by two related ways: 1) The condensation of benzhydrol (I) with chloroacetic acid (II) by means of thiourea (III) in concentrated hydrobromic acid at 95 C gives 2-(diphenylmethylthio)acetic acid (IV), which by reaction with SOCl2 in refluxing benzene is converted into the acid chloride (V). The reaction of (V) with ammonium hydroxide in water - methylene chloride affords 2-(diphenylmethylthio)acetamide (VI), which is finally oxidized with hydrogen peroxide. 2) Acid (IV) can also be oxidized with hydrogen peroxide to give 2-(diphenylmethylsulfinyl)acetic acid (VII), which is methylated with dimethylsulfate and NaHCO3 to the corresponding methyl ester (VIII). Finally, this compound is treated with ammonia in anhydrous methanol.
【1】 Lafon, L. (Laboratoires L. Lafon); Acetamide derivs. DE 2809625; FR 2385693; US 4177290 . |
【2】 Prous, J.; Castaner, J.; MODAFINIL. Drugs Fut 1990, 15, 2, 130. |
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) | 11845 | Diphenylmethanol; Benzhydrol | 91-01-0 | C13H12O | 详情 | 详情 |
(II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(III) | 11847 | 2-Chloroacetic acid; Chloroacetic Acid | 79-11-8 | C2H3ClO2 | 详情 | 详情 |
(IV) | 11848 | 2-(Benzhydrylsulfanyl)acetic acid | C15H14O2S | 详情 | 详情 | |
(V) | 11849 | 2-(Benzhydrylsulfanyl)acetyl chloride | C15H13ClOS | 详情 | 详情 | |
(VI) | 11850 | 2-(Benzhydrylsulfanyl)acetamide | C15H15NOS | 详情 | 详情 | |
(VII) | 11851 | 2-(Benzhydrylsulfinyl)acetic acid | C15H14O3S | 详情 | 详情 | |
(VIII) | 11852 | methyl 2-(benzhydrylsulfinyl)acetate | C16H16O3S | 详情 | 详情 |