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【结 构 式】

【分子编号】56728

【品名】7-chloro-2-quinoxalinol

【CA登记号】

【 分 子 式 】C8H5ClN2O

【 分 子 量 】180.59328

【元素组成】C 53.21% H 2.79% Cl 19.63% N 15.51% O 8.86%

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:(III)

The cyclization of 4-chlorophenylene-1,2-diamine (I) with glyoxylic acid (II) in isopropanol gives a mixture of 7-chloroquinoxalin-2-ol (III) and 6-chloroquinoxalin-2-ol (IV), which, without isolation is treated with refluxing POCl3, and the resulting mixture of dichloro compounds is submitted to flash chromatography to obtain the desired 2,7-dichloroquinoxaline (V). The condensation of (V) with 2-(4-hydroxyphenoxy)propionic acid methyl ester (VI) by means of K2CO3 in refluxing acetone affords the ester precursor (VII), which is hydrolyzed with KOH in THF/water and acidified with HCl to provide the racemic 2-[4-(7-chloroquinoxalin-2-yloxy)phenoxy]propionic acid (VIII). Finally, this compound is converted into its sodium salt with NaOH in water.

1 Behrens, C.H.; Dusak, B.A.; Harrison, B.A.; Orwat, M.J. (Bristol-Myers Squibb Co.); (2-Quinoxalinyloxy)phenoxypropanoic acids and related derivs. as anticancer agents. WO 9413647 .
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) 55570 2-Amino-5-chlorobenzamide; 3,4-Diaminochlorobenzene; 4-Chloro-1,2-diaminobenzene; 4-Chloro-1,2-phenylenediamine; 4-Chloro-o-phenylenediamine 95-83-0 C6H7ClN2 详情 详情
(II) 15618 2-Oxoacetic acid; Glyoxylic Acid 298-12-4 C2H2O3 详情 详情
(III) 56728 7-chloro-2-quinoxalinol C8H5ClN2O 详情 详情
(IV) 56729 6-chloro-2-quinoxalinol C8H5ClN2O 详情 详情
(V) 56725 2,7-dichloroquinoxaline 59489-31-5 C8H4Cl2N2 详情 详情
(VI) 56730 Methyl D-2-(4-hydroxyphenoxy)propionate 96562-58-2 C10H12O4 详情 详情
(VII) 56731 methyl 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propanoate C18H15ClN2O4 详情 详情
(VIII) 56732 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propanoic acid C17H13ClN2O4 详情 详情
Extended Information