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【结 构 式】

【分子编号】44360

【品名】7-amino-1,3-benzoxazol-2(3H)-one

【CA登记号】

【 分 子 式 】C7H6N2O2

【 分 子 量 】150.13692

【元素组成】C 56% H 4.03% N 18.66% O 21.31%

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:(IV)

The synthesis of SLV308 was obtained as follows: The first step is the reduction of just one nitro group, which was accomplished by treating 2,6-dinitrophenol (I) with sodium sulfide in the presence of sodium hydrogencarbonate dissolved in a water/MeOH mixture to yield 2-amino-6-nitro-phenol (II) in 62%. To construct the heterocyclic ring, (II) was reacted with carbonyldiimidazole in dry tetrahydrofuran to give the nitro benzoxazolinone (III) almost quantitatively. The reduction of the nitro group of (III) was performed in acetone/Raney-Ni, resulting in the corresponding aniline (IV) (72%). Transforming the aniline (IV) into the piperazine was done by heating (IV) and bis(2-chloroethyl)amine in chlorobenzene at reflux temperature; after 70 hours the desired piperazine (V) was obtained after chromatographic purification in 60% yield. The last step, introduction of the methyl group, was achieved by a reductive amination; formaldehyde, sodium triacetoxyborohydride and triethylamine dissolved in dichloroethane were added to (V). After work-up, chromatographic purification and subsequent treatment with ethanolic HCl, SLV308 was isolated in 81% yield.

1 van Scharrenburg, G.; Feenstra, R.; Long, S.; Koopman, T.; Stoker, M.; de Vries, M.; Ronken, E.; van Charldorp, K.; McCreary, A.; SLV308. Drugs Fut 2001, 26, 2, 128.
2 Feenstra, R.W.; Visser, G.M.; Van der Heijden, J.A.M.; Long, S.K.; Toorop, G.P.; Van Scharrenburg, G.J.M.; Kruse, C.G.; Mos, J.; Toorop, A.G. (Duphar International Research BV); New piperazine and piperidine cpds.. WO 0029397 .
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) 44357 2,6-dinitrophenol 573-56-8 C6H4N2O5 详情 详情
(II) 44358 2-amino-6-nitrophenol C6H6N2O3 详情 详情
(III) 44359 7-nitro-1,3-benzoxazol-2(3H)-one C7H4N2O4 详情 详情
(IV) 44360 7-amino-1,3-benzoxazol-2(3H)-one C7H6N2O2 详情 详情
(V) 21583 2-chloro-N-(2-chloroethyl)-1-ethanamine; Bis(2-chloroethyl)amine; 1,1'-iminobis(2-chloroethane); N,N-bis(2-chloroethyl)amine 821-48-7 C4H9Cl2N 详情 详情
(VI) 44361 7-(1-piperazinyl)-1,3-benzoxazol-2(3H)-one C11H13N3O2 详情 详情
Extended Information