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【结 构 式】

【分子编号】63379

【品名】3-[4-(cyanosulfanyl)-5-methyl-2-oxo-1(2H)-pyrimidinyl]-N-{[(phenylmethyl)oxy]carbonyl}alanine

【CA登记号】

【 分 子 式 】C17H16N4O5S

【 分 子 量 】388.404

【元素组成】C 52.57% H 4.15% N 14.42% O 20.6% S 8.26%

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:(VI)

The title compound has been prepared by solid-phase combinatorial synthesis. The protected diaminopropionic acid (I) is attached to 2-chlorotrityl resin, producing the resin-bound amino acid (II). The N-Fmoc group of (II) is then selectively removed by treatment with piperidine in DMF producing (III). Condensation of amine (III) with N-ethoxycarbonyl-2-methyl-3-piperidinothioacrylamide (IV) results in the thiouracil derivative (V). This is converted into the thiocyanate (VI) upon treatment with cyanogen bromide in the presence of diisopropylethylamine. Further displacement of the thiocyanate group of (VI) with N-(2-benzimidazolyl)-1,3-propanediamine (VII) leads to the aminopyrimidone resin (VIII). Finally, acidic cleavage from the solid support (VIII) gives rise to the desired compound.

1 Zechel, C.; Backfisch, G.; Delzer, J.; Geneste, H.; Graef, C.; Hornberger, W.; Kling, A.; Lange, U.E.W.; Lauterbach, A.; Seitz, W.; Subkowski, T.; Highly potent and selective alphaVbeta3-receptor antagonists: Solid-phase synthesis and SAR of 1-substituted 4-amino-1H-pyrimidin-2-ones. Bioorg Med Chem Lett 2003, 13, 2, 165.
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), (II) 49911 potassium 4-aminobenzenolate C6H6KNO 详情 详情
(III) 18008 (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propionic acid; N(alpha)-Z-L-2,3-diaminopropionic acid 35761-26-3 C11H14N2O4 详情 详情
(IV) 63377 ethyl 2-methyl-3-(1-piperidinyl)-2-propenethioylcarbamate C12H20N2O2S 详情 详情
(V) 63378 3-[5-methyl-2-oxo-4-thioxo-3,4-dihydro-1(2H)-pyrimidinyl]-N-{[(phenylmethyl)oxy]carbonyl}alanine C16H17N3O5S 详情 详情
(VI) 63379 3-[4-(cyanosulfanyl)-5-methyl-2-oxo-1(2H)-pyrimidinyl]-N-{[(phenylmethyl)oxy]carbonyl}alanine C17H16N4O5S 详情 详情
(VII) 63380 N~1~-(1H-benzimidazol-2-yl)-1,3-propanediamine C10H14N4 详情 详情
(VIII) 63381 3-[4-{[3-(1H-benzimidazol-2-ylamino)propyl]amino}-5-methyl-2-oxo-1(2H)-pyrimidinyl]-N-{[(phenylmethyl)oxy]carbonyl}alanine C26H29N7O5 详情 详情
Extended Information