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【结 构 式】

【分子编号】54747

【品名】3-(benzyloxy)-2-(hydroxymethyl)-1,6-dimethyl-4(1H)-pyridinone

【CA登记号】

【 分 子 式 】C15H17NO3

【 分 子 量 】259.30492

【元素组成】C 69.48% H 6.61% N 5.4% O 18.51%

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:(V)

The reaction of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (I) with SOCl2, followed by dechlorination with Zn/HCl, gives 5-hydroxy-2-methyl-4H-pyran-4-one (II), which is condensed with formaldehyde to yield 3-hydroxy-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one (III). The protection of the aromatic OH group of (III) with Bn-Br affords the benzyl ether (IV), which is treated with methylamine to provide the corresponding 4-pyridone (V). The reaction of the OH group of (V) with phthalimide (VI) by means of DEAD and PPh3 gives the expected phthalimido derivative (VII), which is cleaved with hydrazine to yield the aminomethyl derivative (VIII). The condensation of the amino group of (VIII) with the activated amide (IX) (obtained by condensation of N-propylsuccinamic acid (X) with 2-thiazolidinone (XI) by means of DCC and DMAP) affords the adduct (XII), which is finally debenzylated by hydrogenation with H2 over Pd/C to provide the target succinamide derivative.

1 Liu, Z.D.; et al.; Design, synthesis, and evaluation of novel 2-substituted 3-hydroxypyridin-4-ones: Structure-activity investigation of metalloenzyme inhibition by iron chelators. J Med Chem 2002, 45, 3, 631.
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) 13501 Kojic acid; 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 501-30-4 C6H6O4 详情 详情
(II) 45934 5-hydroxy-2-methyl-4H-pyran-4-one C6H6O3 详情 详情
(III) 48643 3-hydroxy-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one C7H8O4 详情 详情
(IV) 48644 3-(benzyloxy)-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one C14H14O4 详情 详情
(V) 54747 3-(benzyloxy)-2-(hydroxymethyl)-1,6-dimethyl-4(1H)-pyridinone C15H17NO3 详情 详情
(VI) 12376 Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione 85-41-6 C8H5NO2 详情 详情
(VII) 54748 2-{[3-(benzyloxy)-1,6-dimethyl-4-oxo-1,4-dihydro-2-pyridinyl]methyl}-1H-isoindole-1,3(2H)-dione C23H20N2O4 详情 详情
(VIII) 54749 2-(aminomethyl)-3-(benzyloxy)-1,6-dimethyl-4(1H)-pyridinone C15H18N2O2 详情 详情
(IX) 54750 4-oxo-N-propyl-4-(2-thioxo-1,3-thiazolidin-3-yl)butanamide C10H16N2O2S2 详情 详情
(X) 54752 4-oxo-4-(propylamino)butanoic acid C7H13NO3 详情 详情
(XI) 54751 Thiazolidine-2-thione C3H5NS2 详情 详情
(XII) 54753 N~1~-{[3-(benzyloxy)-1,6-dimethyl-4-oxo-1,4-dihydro-2-pyridinyl]methyl}-N~4~-propylsuccinamide C22H29N3O4 详情 详情
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