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【结 构 式】

【分子编号】18897

【品名】2-methyl-2-[[(Z)-(6-methyl-6H-indolo[2,3-b]quinoxalin-4-yl)methylidene]amino]-1,3-propanediol

【CA登记号】

【 分 子 式 】C20H20N4O2

【 分 子 量 】348.40456

【元素组成】C 68.95% H 5.79% N 16.08% O 9.18%

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:(IX)

The condensation of methyl 2,3-diaminobenzoate (I) with isatin (II) in refluxing AcOH afforded a mixture of indoloquinoxaline-carboxylates (III) and (IV), which were separated by column chromatography. The desired 4-carboxylate isomer (III) was methylated at the indole N atom with CH3I in the presence of NaH to provide (V). The ester group of (V) was reduced to alcohol (VI) with LiAlH4 and then oxidized with activated MnO2 to yield aldehyde (VII). Subsequent condensation of (VII) with amine (VIII) in refluxing toluene in the presence of p-toluenesulfonic acid produced the corresponding imine (IX), which was finally reduced with NaBH4 in EtOH to the target amine, which was isolated as the hydrochloride salt.

1 Matsumoto, T.; Wada, H.; Migita, Y.; Hatayama, K.; Sekiguchi, Y. (Taisho Pharmaceutical Co., Ltd.); Indolo[2,3-b]quinoxaline derivs.. EP 0695754; JP 1995522993; WO 9424135 .
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) 18889 methyl 2,3-diaminobenzoate C8H10N2O2 详情 详情
(II) 14098 2,3-Indolinedione; 1H-Indole-2,3-dione; Isatin 91-56-5 C8H5NO2 详情 详情
(III) 18891 methyl 6H-indolo[2,3-b]quinoxaline-4-carboxylate C16H11N3O2 详情 详情
(IV) 18892 methyl 6H-indolo[2,3-b]quinoxaline-1-carboxylate C16H11N3O2 详情 详情
(V) 18893 methyl 6-methyl-6H-indolo[2,3-b]quinoxaline-4-carboxylate C17H13N3O2 详情 详情
(VI) 18894 (6-methyl-6H-indolo[2,3-b]quinoxalin-4-yl)methanol C16H13N3O 详情 详情
(VII) 18895 6-methyl-6H-indolo[2,3-b]quinoxaline-4-carbaldehyde C16H11N3O 详情 详情
(VIII) 11770 2-Amino-2-methyl-1,3-propanediol 115-69-5 C4H11NO2 详情 详情
(IX) 18897 2-methyl-2-[[(Z)-(6-methyl-6H-indolo[2,3-b]quinoxalin-4-yl)methylidene]amino]-1,3-propanediol C20H20N4O2 详情 详情
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