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【结 构 式】

【分子编号】15293

【品名】3-nitrobenzoyl chloride; m-nitrobenzoyl chloride

【CA登记号】121-90-4

【 分 子 式 】C7H4ClNO3

【 分 子 量 】185.5664

【元素组成】C 45.31% H 2.17% Cl 19.11% N 7.55% O 25.87%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(V)

Several procedures for obtaining titte compound have been reported: In one method the acylation of 1 naphthylamine 4,6,8-trisulfonic acid trisodium salt (I) with 4 methyl-3-nitrobenzoyt chloride (II) yields the correspond ing amide (III), which is reduced with Fe in acetic acid to the amine (IV). Acylation of (IV) with 3-nitrobenzoyl chloride (V) affords the nitro diamide (VI), which is reduced with Fe and acetic acid before to the amine (VII). Finally, this compound is condensed with phosgene.

1 Heymann; Angew Chem 1924, 37, 585.
2 Freres, P.; Foruneau, E.; Trefouel, J.; The manufacture of a symmetrical urea of m-aminobenzoyl-m-aminomethylbenzoyl-1-napthylamino-4,6,8-trisulphonate of sodium. GB 224849 .
3 Fourneau; et al.; Compt Rend Acad Sci 1924, 178, 675.
4 Castaner, J.; Serradell, M.N.; Suramin Sodium. Drugs Fut 1986, 11, 10, 860.
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) 23913 8-Aminonaphthalene-1,3,5-trisulfonic acid trisodium salt C10H6NNa3O9S3 详情 详情
(II) 23914 4-methyl-3-nitrobenzoyl chloride 10397-30-5 C8H6ClNO3 详情 详情
(III) 23915 4-Methyl-3-nitro-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt C18H11N2Na3O12S3 详情 详情
(IV) 23916 3-Amino-4-methyl-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt C18H13N2Na3O10S3 详情 详情
(V) 15293 3-nitrobenzoyl chloride; m-nitrobenzoyl chloride 121-90-4 C7H4ClNO3 详情 详情
(VI) 23918 4-Methyl-3-(3-nitrobenzamido)-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt C25H16N3Na3O13S3 详情 详情
(VII) 23919 3-(3-Aminobenzamido)-4-methyl-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt C25H18N3Na3O11S3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

The Friedel-Crafts condensation of indole (I) with 3-nitrobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(3-nitrobenzoyl)indole (III), which is allowed to react with ethyl 4-bromobutyrate (IV) by means of K2CO3 in DMF to yield 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid ethyl ester (V). The hydrolysis of (V) with NaOH in dioxane/water affords the corresponding butyric acid (VI), which is hydrogenated with H2 over Pd/C in methanol/dioxane yielding 3-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (VII). Finally, this compound is condensed with bis(4-isobutylphenyl)chloromethane (VIII) by means of ethyldiisopropylamine in dichloromethane.

1 Mealy, N.; Castaner, J.; FK-143. Drugs Fut 1996, 21, 5, 473.
2 Golden, P.; Hashimoto, M.; Tanaka, H.; Sawada, Y.; Okada, S.; Sawada, K.; Kayakiri, N.; 4-(1-Benzoylindol-3-yl)butyric acids and FK143: Novel nonsteroidal inhibitors of steroid 5alpha-reductase (II). Chem Pharm Bull 1999, 47, 4, 481.
3 Okada, S.; Sawada, K.; Kayakiri, N.; Saitoh, Y.; Tanaka, H.; Hashimoto, M. (Fujisawa Pharmaceutical Co., Ltd.); Indole derivs. EP 0458207; JP 1992244061; US 5212320; US 5312829 .
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) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(II) 15293 3-nitrobenzoyl chloride; m-nitrobenzoyl chloride 121-90-4 C7H4ClNO3 详情 详情
(III) 15294 1H-indol-3-yl(3-nitrophenyl)methanone C15H10N2O3 详情 详情
(IV) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(V) 15296 ethyl 4-[3-(3-nitrobenzoyl)-1H-indol-1-yl]butanoate C21H20N2O5 详情 详情
(VI) 15297 4-[3-(3-nitrobenzoyl)-1H-indol-1-yl]butyric acid C19H16N2O5 详情 详情
(VII) 15298 4-[3-(3-aminobenzoyl)-1H-indol-1-yl]butyric acid C19H18N2O3 详情 详情
(VIII) 15299 1-[chloro(4-isobutylphenyl)methyl]-4-isobutylbenzene C21H27Cl 详情 详情
Extended Information