Y-39241, -Drug Synthesis Database

【结构式】

【药物名称】Y-39241

【化学名称】N-[1-[2-(4-Fluorophenyl)ethyl]pyrrolidin-3(S)-yl]adamantane-1-carboxamide hydrochloride hydrate

【CA登记号】267643-59-4 (anhydrous), 267643-59-4 (free base, anhydrous)

【分子式】C₂₃H₃₄ClFN₂O₂

【分子量】424.99103

【开发单位】Mitsubishi Pharma (Originator)

【药理作用】Antiplatelet Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, 5-HT2 Antagonists

合成路线1

Condensation of (S)-3-amino-1-benzylpyrrolidine (I) with 1-adamantanecarbonyl chloride (II) by means of Et3N in dichloromethane affords amide (III), which is then debenzylated by hydrogenolysis over Pd/C and hydrazine monohydrate to provide amine (IV). Subsequent N-alkylation of (IV) with tosylate (V) in acetonitrile in the presence of K2CO3 furnishes the corresponding alylated compound (VI), which is finally converted into the desired hydrochloride monohydrate derivative by first treatment with HCl:isopropanol in ethyl acetate followed by recrystallization in EtOH:H2O using activated carbon.

参考文献中间体

【1】 Kuroita, T.; Sakai, Y.; Fujio, M.; Nakagawa, H.; Matsumoto, Y.; N-[1-(2-phenylethyl)pyrrolidin-3-yl]-1-adamantanecarboxamides as novel 5-HT2 receptor antagonists. Bioorg Med Chem Lett 2000, 10, 21, 2457.
【2】 Kuroita, T.; Nakagawa, H.; Fujio, M. (Welfide Corporation); Pyrrolidine cpds. and medicinal utilization thereof. EP 1125922; WO 0026186 .

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)	48990	(S)-N-Benzyl-3-aminopyrrolidine; (3S)-(+)-1-Benzyl-3-aminopyrrolidine; (3S)-(+)-N-Benzyl-3-amino pyrrolidine	114715-38-7	C₁₁H₁₆N₂	详情	详情
(II)	31216	1-adamantanecarbonyl chloride	2094-72-6	C₁₁H₁₅ClO	详情	详情
(III)	48991	N-[(3S)-1-benzylpyrrolidinyl]-1-adamantanecarboxamide		C₂₂H₃₀N₂O	详情	详情
(IV)	48992	N-[(3R)pyrrolidinyl]-1-adamantanecarboxamide		C₁₅H₂₄N₂O	详情	详情
(V)	45818	2-(4-fluorophenyl)-1-ethanamine; 4-fluorophenethylamine		C₈H₁₀FN	详情	详情
(VI)	48993	N-[(3R)-1-(4-fluorophenethyl)pyrrolidinyl]-1-adamantanecarboxamide		C₂₃H₃₁FN₂O	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(2)