Org-35030, Ro-60-0175, -Drug Synthesis Database

【结构式】

【药物名称】Org-35030, Ro-60-0175

【化学名称】2(S)-1-(6-Chloro-5-fluoro-1H-indol-1-yl)-2-propanamine fumarate

【CA登记号】

【分子式】C₁₅H₁₆ClFN₂O₄

【分子量】342.75717

【开发单位】Roche (Originator), Organon (Not Determined)

【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2C (5-HT1C) Agonists

合成路线1

Condensation of 6-chloro-5-fluoroindole (I) with (R)-2-methyloxyran (II) in the presence of NaH produced the chiral indolylpropanol (III). After conversion of (III) to the corresponding mesylate (IV) with methanesulfonyl chloride and triethylamine, displacement by NaN3 with inversion of the configuration afforded the (S)-azide (V). Subsequent hydrogenation of (V) using PtO2 yielded the title amine, which was isolated as the fumarate salt.

参考文献中间体

【1】 Bos, M. (F. Hoffmann-La Roche AG); 1-Aminoethylindoles. CA 2132883; EP 0655440; US 5494928 .

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)	30025	6-Chloro-5-fluoroindole; 6-Chloro-5-fluoro-1H-indole	122509-72-2	C₈H₅ClFN	详情	详情
(II)	16662	(2R)-2-Methyloxirane; (R)-(+)-Propylene oxide	15448-47-2	C₃H₆O	详情	详情
(III)	30026	(2R)-1-(6-chloro-5-fluoro-1H-indol-1-yl)-2-propanol		C₁₁H₁₁ClFNO	详情	详情
(IV)	30027	(1R)-2-(6-chloro-5-fluoro-1H-indol-1-yl)-1-methylethyl methanesulfonate		C₁₂H₁₃ClFNO₃S	详情	详情
(V)	30028	1-[(2S)-2-azidopropyl]-6-chloro-5-fluoro-1H-indole; (1S)-2-(6-chloro-5-fluoro-1H-indol-1-yl)-1-methylethyl azide		C₁₁H₁₀ClFN₄	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)