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【结 构 式】 
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【分子编号】25172 【品名】6-methyl-5-(1-pyrrolidinylmethyl)-1,4-dihydro-2,3-quinoxalinedione 【CA登记号】 |
【 分 子 式 】C14H17N3O2 【 分 子 量 】259.308 【元素组成】C 64.85% H 6.61% N 16.2% O 12.34% |
合成路线1
该中间体在本合成路线中的序号：(VIII)2-Amino-6-methylbenzoic acid (I) was reduced to alcohol (II) using LiAlH4, and then acetylated in Ac2O at 50 C. The acetyl protected compound (III) was nitrated with HNO3 in AcOH to afford (IV), which was hydrolyzed to the nitroaniline (V) with methanolic KOH. Subsequent condensation with pyrrolidine (VI) in the presence of diethyl azodicarboxylate and triphenylphosphine provided tertiary amine (VII). Hydrogenation of the nitro group of (VII) over Raney-Ni gave phenylenediamine (VIII), which was cyclized with dimethyl oxalate to produce quinoxalinedione (IX). This was finally nitrated with KNO3 in H2SO4 to furnish the title compound.
| 【1】 Kornberg, B.E.; Nikam, S.; Rafferty, M.F.; Yuen, P.-W. (Pfizer Inc.); Cyclic amine derivs. of substd. quinoxaline 2,3-diones as glutamate receptor antagonists. JP 1999506724; US 5874426; WO 9640650 . |
| 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) | 25165 | 2-amino-6-methylbenzoic acid | 4389-50-8 | C8H9NO2 | 详情 | 详情 |
| (II) | 25166 | (2-amino-6-methylphenyl)methanol | C8H11NO | 详情 | 详情 | |
| (III) | 25167 | 2-(acetamido)-6-methylbenzyl acetate | C12H15NO3 | 详情 | 详情 | |
| (IV) | 25168 | 2-(acetamido)-6-methyl-3-nitrobenzyl acetate | C12H14N2O5 | 详情 | 详情 | |
| (V) | 25169 | (2-amino-6-methyl-3-nitrophenyl)methanol | C8H10N2O3 | 详情 | 详情 | |
| (VI) | 25170 | 3-methyl-6-nitro-2-(1-pyrrolidinylmethyl)aniline | C12H17N3O2 | 详情 | 详情 | |
| (VII) | 25171 | 2-amino-4-methyl-3-(1-pyrrolidinylmethyl)phenylamine | C12H19N3 | 详情 | 详情 | |
| (VIII) | 25172 | 6-methyl-5-(1-pyrrolidinylmethyl)-1,4-dihydro-2,3-quinoxalinedione | C14H17N3O2 | 详情 | 详情 | |
| (IX) | 25173 | 2-pyridinecarbaldehyde | 1121-60-4 | C6H5NO | 详情 | 详情 |