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【结 构 式】

【分子编号】67674

【品名】ethyl 6-hydroxy-1-naphthoate

【CA登记号】 

【 分 子 式 】C13H12O3

【 分 子 量 】216.23648

【元素组成】C 72.21% H 5.59% O 22.2%

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:(XLIII)

Activation of 6-hydroxy-1-naphthoic acid (I) using CDI, followed by coupling with methylamine hydrochloride (III) in DMF at 90 °C gives amide (V). Condensation of compound (V) with the aryl chloride (VI) using DMAP in 2,6-lutidine or i-PrOH at 130 °C or by means of Cs2CO3, CuI and picolinic acid or acetylacetone (Ullmann reaction) in DMF at 120 °C affords the diaryl ether (VIII), whose benzyl group is finally cleaved using TFA at 90 °C .
Esterification naphthoic acid (I) with EtOH and H2SO4 at reflux yields ethyl 6-hydroxy-1-naphthoic acid (XLIII), which then couples with aryl chloride (VI) in the presence of DMAP in 2,6-lutidine or i-PrOH at 130°C or by means of Cs2CO3, CuI and picolinic acid or acetylacetone in DMF at 120 °C (Ullmann reaction) to give diayl ether (XLIV). Finally, this compound is debenzylated with TFA at 90 °C .

1 Chen, G.P. (Advenchen Laboratories, LLC). Process for preparing the antitumor agent 6-(7-((1-aminocyclopropyl) methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide and its crystalline. WO 2014113616.
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) 67625 6-hydroxy-1-naphthoic acid;6-Hydroxy-1-naphthalenecarboxylic acid 2437-17-4 C11H8O3 详情 详情
(III) 67627 methanamine hydrochloride   CH5N.HCl 详情 详情
(V) 67629 6-hydroxy-N-methyl-1-naphthamide   C12H11NO2 详情 详情
(VI) 67630 7-benzyloxy-6-methoxy-4-chloroquinoline   C17H14ClNO2 详情 详情
(VIII) 67632 6-((7-(benzyloxy)-6-methoxyquinolin-4-yl)oxy)-N-methyl-1-naphthamide   C29H24N2O4 详情 详情
(IX) 67633 6-((7-hydroxy-6-methoxyquinolin-4-yl)oxy)-N-methyl-1-naphthamide   C22H18N2O4 详情 详情
(XL) 67670 ethyl 6-((7-hydroxy-6-methoxyquinolin-4-yl)oxy)-1-naphthoate C23H19NO5 详情 详情
(XLIII) 67674 ethyl 6-hydroxy-1-naphthoate   C13H12O3 详情 详情
(XLIV) 67675 ethyl 6-((7-(benzyloxy)-6-methoxyquinolin-4-yl)oxy)-1-naphthoate   C30H25NO5 详情 详情
Extended Information