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【结 构 式】

【分子编号】65081

【品名】7,8-diamino-3,4-dimethyl-1(2H)-isoquinolinone

【CA登记号】

【 分 子 式 】C11H13N3O

【 分 子 量 】203.24384

【元素组成】C 65.01% H 6.45% N 20.67% O 7.87%

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:(VI)

In an alternative method, 2,6-dichloro-3-nitrobenzonitrile (I) is heated with ethanolic ammonia in a sealed vessel to produce the 2-amino benzonitrile (II). Subsequent condensation of 2-amino-6-chloro-3-nitrobenzonitrile (II) with ethyl methylacetoacetate (III) in the presence of K2CO3 leads to the aryl methyl acetoacetate ester (IV). Decarboxylation and cyclization of (IV) under acidic conditions then produces isoquinolinone (V). Nitro group reduction in (V) with H2 and Pd/C leads to diamine (VI), which is further coupled with 2,6-dichlorophenyl isothiocyanate (VII), yielding thiourea (VIII). Finally, ring closure of amino thiourea (VIII) with DCC in hot DMF affords the target tricyclic compound (2).

1 Goldberg, D.; Cardozo, M.G.; Tschantz, M.A.; Moss, N.; Morwick, T.; Prokopowicz, A.S. III; Snow, R.J.; Patel, U.R.; Wang, X.-J.; Hammach, A.; Takahashi, H. (Boehringer Ingelheim Pharmaceuticals Inc.); Heterocyclic cpds. useful as inhibitors of tyrosine kinases. WO 0125238 .
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) 52340 2,6-Dichloro-3-nitrobenzonitrile 5866-98-8 C7H2Cl2N2O2 详情 详情
(II) 65079 2-amino-6-chloro-3-nitrobenzonitrile C7H4ClN3O2 详情 详情
(III) 10362 ethyl 2-methyl-3-oxobutanoate; ethyl 2-methylacetoacetate 609-14-3 C7H12O3 详情 详情
(IV) 65080 ethyl 2-(3-amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutanoate C14H15N3O5 详情 详情
(V) 65082 8-amino-3,4-dimethyl-7-nitro-1(2H)-isoquinolinone C11H11N3O3 详情 详情
(VI) 65081 7,8-diamino-3,4-dimethyl-1(2H)-isoquinolinone C11H13N3O 详情 详情
(VII) 52344 2,6-Dichlorophenyl isothiocyanate 6590-95-0 C7H3Cl2NS 详情 详情
(VIII) 65083 N-(8-amino-3,4-dimethyl-1-oxo-1,2-dihydro-7-isoquinolinyl)-N'-(2,6-dichlorophenyl)thiourea C18H16Cl2N4OS 详情 详情
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