1,5-di(4-pyridinyl)-3-pentanone -Drug Synthesis Database

【结构式】

【分子编号】30041

【品名】1,5-di(4-pyridinyl)-3-pentanone

【CA登记号】

【分子式】C₁₅H₁₆N₂O

【分子量】240.30492

【元素组成】C 74.97% H 6.71% N 11.66% O 6.66%

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：(IV)

Condensation of 1,3-acetonedicarboxylic acid (I) with pyridine-4-carboxaldehyde (II) and subsequent acid decarboxylation produced 1,5-dipyridylpentadienone (III), which was reduced to the saturated ketone (IV) by transfer hydrogenation using formic acid and Pd/C. Condensation of (IV) with benzyl amine (V) in benzene with azeotropical removal of water, followed by reduction of the intermediate imine with NaBH4 gave rise to the secondary amine (VI). Coupling of (VI) with N-Boc-N-methyl-L-4-chlorophenylalanine (VII) in the presence of EDC afforded amide (VIII). After Boc deprotection of (VIII) with trifluoroacetic acid, the resulting amine (IX) was coupled with 3,4,5-trimethoxybenzoylformic acid (X) to furnish the title compound.

参考文献中间体

合成目标

【1】 Zelle, R.E.; Harding, M.W. (Vertex Pharmaceuticals Inc.); Novel amino acid derivs. with improved multi-drug resistance activity. EP 0797567; JP 1998509151; US 5543423; WO 9615101 .
【2】 Zelle, R.E. (Vertex Pharmaceuticals Inc.); Methods and compsns. for stimulating neurite growth using cpds. with affinity for FKBP2 in combination with neurotrophic factors. WO 9820891 .

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)	15530	1,3-Acetonedicarboxylic Acid; 3-Oxopentanedioic acid；3-oxoglutaric acid	542-05-2	C₅H₆O₅	详情	详情
(II)	17203	4-Pyridinecarboxaldehyde; isonicotinaldehyde	872-85-5	C₆H₅NO	详情	详情
(III)	30040	(1E,4E)-1,5-di(4-pyridinyl)-1,4-pentadien-3-one		C₁₅H₁₂N₂O	详情	详情
(IV)	30041	1,5-di(4-pyridinyl)-3-pentanone		C₁₅H₁₆N₂O	详情	详情
(V)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(VI)	30042	N-benzyl-1,5-di(4-pyridinyl)-3-pentanamine; N-benzyl-N-[3-(4-pyridinyl)-1-[2-(4-pyridinyl)ethyl]propyl]amine		C₂₂H₂₅N₃	详情	详情
(VII)	30043	(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-(4-chlorophenyl)propionic acid	125324-00-7	C₁₅H₂₀ClNO₄	详情	详情
(VIII)	30044	tert-butyl (1S)-2-(benzyl[3-(4-pyridinyl)-1-[2-(4-pyridinyl)ethyl]propyl]amino)-1-(4-chlorobenzyl)-2-oxoethyl(methyl)carbamate		C₃₇H₄₃ClN₄O₃	详情	详情
(IX)	30045	(2S)-N-benzyl-3-(4-chlorophenyl)-2-(methylamino)-N-[3-(4-pyridinyl)-1-[2-(4-pyridinyl)ethyl]propyl]propanamide		C₃₂H₃₅ClN₄O	详情	详情
(X)	30046	2-oxo-2-(3,4,5-trimethoxyphenyl)acetic acid		C₁₁H₁₂O₆	详情	详情

Extended Information