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【结 构 式】

【分子编号】41771

【品名】1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

【CA登记号】

【 分 子 式 】C10H7F2N3O2

【 分 子 量 】239.1814064

【元素组成】C 50.22% H 2.95% F 15.89% N 17.57% O 13.38%

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:(III)

Rufinamide has been obtained by several related ways: 1) Cyclization of 2,6-difluorobenzyl azide (I) with 2-propynoic acid (II) in hot toluene gives 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (III), which is treated with refluxing SOCl2 to yield the corresponding acyl chloride (IV). Finally, this compound is treated with aqueous concentrated NH4OH. 2) Cyclization of 2,6-difluorobenyzl azide (I) with 2-chloroacrylonitrile (V) in hot water or n-heptane gives 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carbonitrile (VI), which is treated with NaOH in hot toluene/water. 3) Esterification of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (III) with methanol/H2SO4 gives the corresponding methyl ester (VII), which is treated with NH3 in hot methanol.

1 Leeson, P.A.; Sorbera, L.A.; Rabasseda, X.; Castaner, J.; Rufinamide. Drugs Fut 2000, 25, 11, 1145.
2 Meier, R. (Novartis AG); Fluorinated benzyltriazole derivs.. AU 8656319; EP 0199262; ES 8800176; ES 8802501; JP 1986243068 .
3 Portmann, R. (Novartis AG); Process for preparing 1-substd. 4-cyano-1,2,3-triazoles. WO 9802423 .
4 Burkhard, A.; Szelagiewicz, M.; Hofmeier, U.C.; Portmann, R.; Scherrer, W. (Novartis AG); Crystal modification of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and its use as antiepileptic. WO 9856772; WO 9856773 .
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) 41769 2,6-difluorobenzyl azide; 2-(azidomethyl)-1,3-difluorobenzene C7H5F2N3 详情 详情
(II) 41770 propiolic acid 471-25-0 C3H2O2 详情 详情
(III) 41771 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid C10H7F2N3O2 详情 详情
(IV) 41772 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carbonyl chloride C10H6ClF2N3O 详情 详情
(V) 12372 2-Chloroacrylonitrile 920-37-6 C3H2ClN 详情 详情
(VI) 41773 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carbonitrile C10H6F2N4 详情 详情
(VII) 41774 methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate C11H9F2N3O2 详情 详情
Extended Information