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【结 构 式】

【分子编号】41155

【品名】1H-imidazol-2-ylamine; 1H-imidazol-2-amine; 2-Aminoimidazole

【CA登记号】7720-39-0

【 分 子 式 】C3H5N3

【 分 子 量 】83.09292

【元素组成】C 43.36% H 6.07% N 50.57%

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)

Cycloaddition of 5-hexen-1-ol (I) with (II) in presence of NaHCO3 yields isoxazoline (III). Alternatively (III) can be obtained by treatment of (I) with diethyl nitromalonate (A) in mesitylene. Isoxazoline (III) is then oxidized by means of Jones reagent to provide acid (IV) which is coupled in presence of BOP with the imidazole derivative (V) and hydrolyzed with LiOH affording derivative (VI). Acid (VI) is coupled with derivative (IX) (obtained by reaction of diaminopropionate (VII) with (VIII) in presence of DIEA) by means of BOP, and finally hydrolyzed to afford the desired product.

1 Withyak, J.; Pitts, W.J.; Smallheer, J.M.; et al.; Isoxazolines as potent antagonists of the integrin alphavbeta3. J Med Chem 2000, 43, 1, 27.
2 Voss, M.E.; Jadhav, P.K.; Smallheer, J.M.; Batt, D.G.; Pitts, W.J.; Wityak, J. (DuPont Pharmaceuticals Co.); Isoxazoline and isoxazole derivs. as integrin receptor antagonists. EP 0828737; JP 1999506436; US 5710159; WO 9637492 .
3 Jadhav, P.; Repta, A.J.; Pitts, W.J.; Hussain, M.A.; Batt, D.G. (DuPont Pharmaceuticals Co.); Heterocyclic integrin inhibitor prodrugs. WO 9843962 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 41159 diethyl 2-nitromalonate C7H11NO6 详情 详情
(I) 41152 5-hexen-1-ol 821-41-0 C6H12O 详情 详情
(II) 30424 2-ethoxy-N-hydroxy-2-oxoethanimidoyl chloride 14337-43-0 C4H6ClNO3 详情 详情
(III) 41153 ethyl 5-(4-hydroxybutyl)-4,5-dihydro-3-isoxazolecarboxylate C10H17NO4 详情 详情
(IV) 41154 4-[3-(ethoxycarbonyl)-4,5-dihydro-5-isoxazolyl]butyric acid C10H15NO5 详情 详情
(V) 41155 1H-imidazol-2-ylamine; 1H-imidazol-2-amine; 2-Aminoimidazole 7720-39-0 C3H5N3 详情 详情
(VI) 41156 5-[4-(1H-imidazol-2-ylamino)-4-oxobutyl]-4,5-dihydro-3-isoxazolecarboxylic acid C11H14N4O4 详情 详情
(VII) 41157 tert-butyl (2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoate C12H24N2O4 详情 详情
(VIII) 41158 2,4,6-trimethylbenzenesulfonyl chloride 773-64-8 C9H11ClO2S 详情 详情
(IX) 36588 tert-butyl (2S)-3-amino-2-[(mesitylsulfonyl)amino]propanoate C16H26N2O4S 详情 详情
Extended Information