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【结 构 式】

【分子编号】53880

【品名】2-(2-carboxyanilino)-3-methoxybenzoic acid

【CA登记号】n/a

【 分 子 式 】C15H13NO5

【 分 子 量 】287.27196

【元素组成】C 62.72% H 4.56% N 4.88% O 27.85%

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:(VIII)

The condensation of 2-(4-nitrophenyl)ethyl bromide (I) with 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (II) by means of K2CO3 and KI in DMF at 100 C gives 6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline (III), which is reduced with H2 over Pd/C in ethanol to yield the corresponding amine (IV). Finally, this compound is condensed with 5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylic acid (V) by means of DCC and HOBt in DMF to afford the target carboxamide. The intermediate 5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylic acid (V) has been obtained as follows: The condensation of 2-amino-3-methoxybenzoic acid (VI) with 2-bromobenzoic acid (VII) by means of K2CO3 and copper dust give the diphenylamine (VIII), which is cyclized to the target acridine (V) by means of POCl3 in refluxing acetonitrile.

1 Dodic, N.; et al.; Synthesis and activity against multidrug resistance in Chinese hamster ovary cells of new acridone-4-carboxamides. J Med Chem 1995, 38, 13, 2418.
2 Dumaitre, B.A.; Dodic, N. (GlaxoSmithKline plc); Acridine derivs.. EP 0494623; EP 0569380; JP 1994506440; US 5604237; WO 9212132 .
3 Sharp, M.J.; Mader, C.J.; Strachan, C. (GlaxoSmithKline plc); Synthesis of acridine deriv. multidrug-resistant inhibitors. WO 9852923 .
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) 19191 1-(2-bromoethyl)-4-nitrobenzene 5339-26-4 C8H8BrNO2 详情 详情
(II) 25859 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether C11H15NO2 详情 详情
(III) 19193 6,7-dimethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline; 6-methoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether C19H22N2O4 详情 详情
(IV) 19194 4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]aniline; 4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]phenylamine C19H24N2O2 详情 详情
(V) 53881 5-methoxy-9-oxo-9,10-dihydro-4-acridinecarboxylic acid n/a C15H11NO4 详情 详情
(VI) 53879 2-Amino-3-methoxybenzoic acid; 2-Amino-m-anisic acid; 3-Methoxyanthranilic acid 3177-80-8 C8H9NO3 详情 详情
(VII) 15546 2-bromobenzoic acid; o-bromobenzoic acid 88-65-3 C7H5BrO2 详情 详情
(VIII) 53880 2-(2-carboxyanilino)-3-methoxybenzoic acid n/a C15H13NO5 详情 详情
Extended Information