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【结 构 式】

【分子编号】30045

【品名】(2S)-N-benzyl-3-(4-chlorophenyl)-2-(methylamino)-N-[3-(4-pyridinyl)-1-[2-(4-pyridinyl)ethyl]propyl]propanamide

【CA登记号】

【 分 子 式 】C32H35ClN4O

【 分 子 量 】527.10896

【元素组成】C 72.92% H 6.69% Cl 6.73% N 10.63% O 3.04%

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:(IX)

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.

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