Ro-44-2104, -Drug Synthesis Database

【结构式】

【药物名称】Ro-44-2104

【化学名称】4'-(N-Allyl-N-methylaminomethyl)-4-biphenylyl-4-bromophenyl ketone

【CA登记号】140620-63-9, 140621-14-3 (HCl)

【分子式】C₂₄H₂₂BrNO

【分子量】420.35304

【开发单位】Roche (Originator)

【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY, Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Lanosterol Synthase Inhibitors

合成路线1

Grignard reagent (II) prepared from 1,4-dibromobenzene (I) was condensed with biphenylaldehyde (III) to afford alcohol (IV), which was oxidized to ketone (V) under Swern conditions with oxalyl chloride and DMSO at low temperature. Then, allylic bromination with N-bromosuccinimide (NBS) in the presence of azobisisobutyronitrile (AIBN) gave (VI). Finally, N-allyl-N-methylamine (VII) was alkylated with bromide (VI) to provide the tertiary amine.

参考文献中间体

【1】 Aebi, J.; Guerry, P.; Jolidon, S.; Morand, O. (F. Hoffmann-La Roche AG); Use of phenylalkylamines for producing cholesterol lowering agents. EP 0636367; JP 1995053479; US 5637771 .

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)	18983	1,4-dibromobenzene	106-37-6	C₆H₄Br₂	详情	详情
(II)	18984	bromo(4-bromophenyl)magnesium		C₆H₄Br₂Mg	详情	详情
(III)	18985	4'-methyl[1,1'-biphenyl]-4-carbaldehyde		C₁₄H₁₂O	详情	详情
(IV)	18986	(4-bromophenyl)(4'-methyl[1,1'-biphenyl]-4-yl)methanol		C₂₀H₁₇BrO	详情	详情
(V)	18987	(4-bromophenyl)(4'-methyl[1,1'-biphenyl]-4-yl)methanone		C₂₀H₁₅BrO	详情	详情
(VI)	18988	[4'-(bromomethyl)[1,1'-biphenyl]-4-yl](4-bromophenyl)methanone		C₂₀H₁₄Br₂O	详情	详情
(VII)	18989	N-allyl-N-methylamine; N-methyl-2-propen-1-amine	627-37-2	C₄H₉N	详情	详情

Extended Information