• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】48449

【品名】(2,3-dimethoxy-7-nitro-5-quinoxalinyl)methanamine; (2,3-dimethoxy-7-nitro-5-quinoxalinyl)methylamine

【CA登记号】

【 分 子 式 】C11H12N4O4

【 分 子 量 】264.24084

【元素组成】C 50% H 4.58% N 21.2% O 24.22%

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)

Treatment of diamino compound (I) with oxalic acid (II) in refluxing HCl provides tetrahydroquinoxalindione derivative (III), which is then converted into dichloro compound (IV) by reaction with refluxing POCl3. Treatment of (IV) with Na in refluxing MeOH affords dimethoxy quinoxaline (V), which is then brominated by reaction with NBS and AIBN in refluxing CCl4 to give bromomethyl derivative (VI). Nitration of (VI) by reaction with isopropyl nitrate in H2SO4 yields nitro derivative (VII), which is then converted into protected amino methyl derivative (IX) by reaction with di-tert-butyl-iminocarboxylate (VIII) and cesium carbonate in DMF. Removal of the Boc groups of (IX) by means of TFA gives aminomethyl derivative (X), which is then converted into phosphonic dimethyl ester (XII) by first treatment with formaline in EtOH followed by reaction with dimethyl phosphonate (XI), Et3N and trimethylsilyl chloride (TMSCl) in CHCl3. Finally, treatment of (XII) with trimethylsilyl bromide (TMSBr) in CH2Cl2 obtains the desired product.

1 Acklin, P.; Allgeier, H.; Auberson, Y.; Ofner, S.; Veenstra, S.J. (Novartis AG); Substd. aminoalkane phosphonic acids. EP 0934326; US 6117873; WO 9817672 .
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) 48441 2,3-Diaminotoluene; o-Tolylenediamine 2687-25-4 C7H10N2 详情 详情
(II) 15713 Oxalic acid 144-62-7 C2H2O4 详情 详情
(III) 48442 5-methyl-1,4-dihydro-2,3-quinoxalinedione C9H8N2O2 详情 详情
(IV) 48443 2,3-dichloro-5-methylquinoxaline C9H6Cl2N2 详情 详情
(V) 48444 2,3-dimethoxy-5-methylquinoxaline; 3-methoxy-5-methyl-2-quinoxalinyl methyl ether C11H12N2O2 详情 详情
(VI) 48445 5-(bromomethyl)-3-methoxy-2-quinoxalinyl methyl ether; 5-(bromomethyl)-2,3-dimethoxyquinoxaline C11H11BrN2O2 详情 详情
(VII) 48446 5-(bromomethyl)-3-methoxy-7-nitro-2-quinoxalinyl methyl ether; 5-(bromomethyl)-2,3-dimethoxy-7-nitroquinoxaline C11H10BrN3O4 详情 详情
(VIII) 48447 Di-tert-butyl iminodicarboxylate; Iminodicarboxylic acid di-tert-butyl ester 51779-32-9 C10H19NO4 详情 详情
(IX) 48448 5-[[bis(tert-butoxycarbonyl)amino]methyl]-2,3-dimethoxy-7-nitroquinoxaline C21H28N4O8 详情 详情
(X) 48449 (2,3-dimethoxy-7-nitro-5-quinoxalinyl)methanamine; (2,3-dimethoxy-7-nitro-5-quinoxalinyl)methylamine C11H12N4O4 详情 详情
(XI) 32359 dimethyl phosphonate 868-85-9 C2H7O3P 详情 详情
(XII) 48450 dimethyl [[(2,3-dimethoxy-7-nitro-5-quinoxalinyl)methyl]amino]methylphosphonate C14H19N4O7P 详情 详情
Extended Information