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【结 构 式】

【分子编号】62378

【品名】(3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

【CA登记号】

【 分 子 式 】C15H19ClN6O4

【 分 子 量 】382.8066

【元素组成】C 47.06% H 5% Cl 9.26% N 21.95% O 16.72%

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:(X)

Acetonide (VII) was prepared by treatment of 2-chloroadenosine (VI) with 2,2-dimethoxypropane and camphorsulfonic acid. Subsequent oxidation of (VII) with KMnO4 under basic conditions produced the carboxylic acid (VIII). After activation of (VIII) as the corresponding acid chloride (IX), reaction with ethylamine afforded amide (X). Condensation of amine (V) with the chloroadenosine derivative (X) at 130 C furnished the diaminopurine adduct (XI). Finally, simultaneous cleavage of the tert-butyl ester and acetonide groups of (XI) upon acidic treatment provided the title compound

1 Hutchison, A.J.; Williams, M.; de Jesus, R.; Yokoyama, R.; Oei, H.H.; Ghai, G.R.; Webb, R.L.; Zoganas, H.C.; Stone, G.A.; Jarvis, M.F.; 2-(Arylalkylamino)adenosin-5'-uronamides: A new class of highly selective adenosine A2 receptor ligands. J Med Chem 1990, 33, 7, 1919.
2 Hutchison, A.J. (Novartis AG); Certain adenosine 5'-carboxamide derivs.. AU 8811233; EP 0277917; JP 1988201196 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 62373 tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate C15H23NO2 详情 详情
(VI) 62374 (2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol C10H12ClN5O4 详情 详情
(VII) 62375 [(3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol C13H16ClN5O4 详情 详情
(VIII) 62376 (3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid C13H14ClN5O5 详情 详情
(IX) 62377 (3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl chloride C13H13Cl2N5O4 详情 详情
(X) 62378 (3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide C15H19ClN6O4 详情 详情
(XI) 62379 tert-butyl 3-(4-{2-[(9-{(3aR,4R,6S,6aR)-6-[(ethylamino)carbonyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-6-amino-9H-purin-2-yl)amino]ethyl}phenyl)propanoate C30H41N7O6 详情 详情
Extended Information