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【结 构 式】

【分子编号】53504

【品名】4-[(4-chlorobenzoyl)amino]benzoic acid

【CA登记号】n/a

【 分 子 式 】C14H10ClNO3

【 分 子 量 】275.69104

【元素组成】C 60.99% H 3.66% Cl 12.86% N 5.08% O 17.41%

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:(XII)

The condensation of 3-ethylphenol (I) with 4-piperidone (II) by means of gaseous HCl in acetic acid gives 5-ethyl-2-(1,2,3,6-tetrahydropyridin-4-yl)phenol (III), which is treated with acetic anhydride in pyridine to yield the diacetyl derivative (IV). The selective hydrolysis of the O-acetyl group of (IV) by means of K2CO3 in methanol affords the phenol derivative (V), which is hydrogenated with H2 over Pd/C in methanol to provide the acetyl piperidine (VI). The alkylation of the phenolic group of (VI) with ethyl iodide and Cs2CO3 in refluxing acetone gives 1-acetyl-4-(2-ethoxy-4-ethylphenyl)piperidine (VII), which is deacetylated by means of NaOH in refluxing methanol to yield 4-(2-ethoxy-4-ethylphenyl)piperidine (VIII). The alkylation of the piperidine (VIII) with N-(4-bromobutyl)phthalimide (IX) by means of Cs2CO3 in refluxing acetone affords the adduct (X), which is cleaved with hydrazine in hot methanol to provide 1-(4-aminobutyl)-4-(2-ethoxy-4-ethylphenyl)piperidine (XI). Finally, this amine is condensed with 4-(4-chlorobenzamido)benzoic acid (XII) by means of EDC, HOBT and TEA in DMF to give the target diamide. The intermediate 4-(4-chlorobenzamido)benzoic acid (XII) is obtained as follows: The condensation of 4-aminobenzoic acid ethyl ester (XIV) with 4-chlorobenzoyl chloride (XIII) by means of TEA and DMAP gives 4-(4-chlorobenzamido)benzoic acid ethyl ester (XV), which is finally hydrolyzed with NaOH to afford the target benzoic acid intermediate (XII).

1 Grand-Perret, T.A.R.; Issandou, M. (GlaxoSmithKline plc); Binding competition of SREBP-cleavage activating protein (SCAP) antagonists. WO 0106261 .
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) 53495 3-Ethyl phenol; m-Ethyl phenol 620-17-7 C8H10O 详情 详情
(II) 27115 4-piperidinone 40064-34-4 C5H9NO 详情 详情
(III) 53496 5-ethyl-2-(1,2,3,6-tetrahydro-4-pyridinyl)phenol n/a C13H17NO 详情 详情
(IV) 53497 2-(1-acetyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-ethylphenyl acetate n/a C17H21NO3 详情 详情
(V) 53498 1-[4-(4-ethyl-2-hydroxyphenyl)-3,6-dihydro-1(2H)-pyridinyl]-1-ethanone n/a C15H19NO2 详情 详情
(VI) 53499 1-[4-(4-ethyl-2-hydroxyphenyl)-1-piperidinyl]-1-ethanone n/a C15H21NO2 详情 详情
(VII) 53500 1-[4-(2-ethoxy-4-ethylphenyl)-1-piperidinyl]-1-ethanone n/a C17H25NO2 详情 详情
(VIII) 53501 4-(2-ethoxy-4-ethylphenyl)piperidine; ethyl 5-ethyl-2-(4-piperidinyl)phenyl ether n/a C15H23NO 详情 详情
(IX) 17163 N-(4-Bromobutyl)phthalimide; 2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione 5394-18-3 C12H12BrNO2 详情 详情
(X) 53502 2-{4-[4-(2-ethoxy-4-ethylphenyl)-1-piperidinyl]butyl}-1H-isoindole-1,3(2H)-dione n/a C27H34N2O3 详情 详情
(XI) 53503 4-[4-(2-ethoxy-4-ethylphenyl)-1-piperidinyl]-1-butanamine; 4-[4-(2-ethoxy-4-ethylphenyl)-1-piperidinyl]butylamine n/a C19H32N2O 详情 详情
(XII) 53504 4-[(4-chlorobenzoyl)amino]benzoic acid n/a C14H10ClNO3 详情 详情
(XIII) 10295 p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride 122-01-0 C7H4Cl2O 详情 详情
(XIV) 16498 Benzocaine; ethyl 4-aminobenzoate 94-09-7 C9H11NO2 详情 详情
(XV) 53505 Ethyl 4-(4-chlorobenzamido)benzoate n/a C16H14ClNO3 详情 详情
Extended Information