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【结 构 式】

【分子编号】40647

【品名】(1R)-1-(2-pyridinyl)-1,2,3,4-tetrahydroisoquinoline

【CA登记号】

【 分 子 式 】C14H14N2

【 分 子 量 】210.27864

【元素组成】C 79.97% H 6.71% N 13.32%

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:(XI)

The condensation between ethyl picolinate (VII) and phenethylamine (VIII) at 180 C produced amide (IX), which was subsequently cyclized to dihydroisoquinoline (X) either by heating with polyphosphoric acid or by chlorination with PCl5, followed by cyclization in the presence of AlCl3. Catalytic hydrogenation of (X) gave rise to the racemic tetrahydroisoquinoline, which was resolved employing D-(-)-tartaric acid. The desired (R)-enantiomer (XI) was acylated with acryloyl chloride (XII) to produce acrylamide (XIII). Finally, palladium-catalyzed coupling of (XIII) with aryl iodide (VI) furnished the title compound.

1 Guerry, P.; Locher, H.H.; Hubschwerlen, C.; Wyss, P.C.; Jolidon, S.; Hartman, P.G.; Stalder, H.; Specklin, J.L.; Anti-MRSA dihydrofolate reductase inhibitors: Synthesis and SAR. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F1800.
2 Guerry, P.; Stalder, H.; Wyss, P.-C. (F. Hoffmann-La Roche AG); 2,4-Diaminopyrimidine derivs.. EP 0901488; JP 1999511749; US 5866583; WO 9743277 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 40643 5-(3-iodo-4,5-dimethoxybenzyl)-2,4-pyrimidinediamine; 2-amino-5-(3-iodo-4,5-dimethoxybenzyl)-4-pyrimidinylamine C13H15IN4O2 详情 详情
(VII) 40644 ethyl 2-pyridinecarboxylate 2524-52-9 C8H9NO2 详情 详情
(VIII) 18333 Phenethylamine; 2-Phenyl-1-ethanamine 64-04-0 C8H11N 详情 详情
(IX) 40645 N-phenethyl-2-pyridinecarboxamide C14H14N2O 详情 详情
(X) 40646 1-(2-pyridinyl)-3,4-dihydroisoquinoline C14H12N2 详情 详情
(XI) 40647 (1R)-1-(2-pyridinyl)-1,2,3,4-tetrahydroisoquinoline C14H14N2 详情 详情
(XII) 11577 Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride 814-68-6 C3H3ClO 详情 详情
(XIII) 40648 1-[(1R)-1-(2-pyridinyl)-3,4-dihydro-2(1H)-isoquinolinyl]-2-propen-1-one C17H16N2O 详情 详情
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