1-[4-bromo-1-(4-fluorophenyl)butyl]-4-fluorobenzene -Drug Synthesis Database

【结构式】

【分子编号】35603

【品名】1-[4-bromo-1-(4-fluorophenyl)butyl]-4-fluorobenzene

【CA登记号】

【分子式】C₁₆H₁₅BrF₂

【分子量】325.1959064

【元素组成】C 59.1% H 4.65% Br 24.57% F 11.68%

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：(I)

Condensation of 4,4-bis(4-fluorophenyl)butyl bromide (I) with potassium phthalimide (II) in hot DMF yielded the substituted phthalimide (III). Deprotection of the phthalimido group of (III) to give primary amine (IV) was effected by treatment with NaBH4, followed by methanolic HCl. Subsequent coupling of (IV) with N-Boc-N-methyl-L-leucine (V) by means of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate furnished amide (VI). Finally, the Boc group of (VI) was deprotected using trifluoroacetic acid in CH2Cl2 and treated with HCl.

参考文献中间体

合成目标

【1】 Song, Y.; Connor, D.T.; Bowersox, S.S.; et al.; (S)-4-methyl-2-(methylamino)pentanoic acid [4,4-bis(4-fluorophenyl)butyl]amide hydrochloride, a novel calcium channel antagonist, is efficacious in several animal models of pain. J Med Chem 2000, 43, 19, 3474.
【2】 Song, Y.; Rafferty, M.F.; Ryder, T.R.; Sercel, A.D.; Connor, D.T.; Malone, T.C.; Hu, L.-Y.; Roth, B.D. (Pfizer Inc.); Substd. diarylalkyl amides as calcium channel antagonists. WO 9955688 .

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)	35603	1-[4-bromo-1-(4-fluorophenyl)butyl]-4-fluorobenzene		C₁₆H₁₅BrF₂	详情	详情
(II)	27890	Potassium phthalimide	1074-82-4	C₈H₄KNO₂	详情	详情
(III)	35604	2-[4,4-bis(4-fluorophenyl)butyl]-1H-isoindole-1,3(2H)-dione		C₂₄H₁₉F₂NO₂	详情	详情
(IV)	35605	4,4-bis(4-fluorophenyl)-1-butanamine; 4,4-bis(4-fluorophenyl)butylamine		C₁₆H₁₇F₂N	详情	详情
(V)	26295	(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoic acid	609-23-4	C₁₂H₂₃NO₄	详情	详情
(VI)	35607	tert-butyl (1S)-1-([[4,4-bis(4-fluorophenyl)butyl]amino]carbonyl)-3-methylbutyl(methyl)carbamate		C₂₈H₃₈F₂N₂O₃	详情	详情

Extended Information