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【结 构 式】 
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【分子编号】22548 【品名】4-[[amino(imino)methyl]amino]benzoyl chloride 【CA登记号】 |
【 分 子 式 】C8H8ClN3O 【 分 子 量 】197.62384 【元素组成】C 48.62% H 4.08% Cl 17.94% N 21.26% O 8.1% |
合成路线1
该中间体在本合成路线中的序号：(III)This compound can be prepared by condensation of 4-guanidinobenzoic acid (I) with 6-amidino-2-naphthol (II) in pyridine either by means of DCC or the acid chloride of (I), (III), at room temperature.
| 【1】 Fujii, S.; Okutome, T.; Nakayama, T.; Yaegashi, T.; Kurumi, M. (Torii Pharmaceutical Co., Ltd.); Amidine compound. JP 82179146; JP 8253454; US 4454338 . |
| 【2】 Aoyama, T.; Nafamstat Mesylate. Drugs Fut 1984, 9, 10, 747. |
合成路线2
该中间体在本合成路线中的序号：(V)The reaction of p-hydrophenylacetic acid (I) with N,N-dimethylbromoacetamide (II) by means of triethylamine in reftuxing acetonitrile gives N,N-dimethylcarbamoylmethyl-p-hydroxyphenylacetate (III), which is then condensed with p-guanidinobenzoyl chloride (IV) [obtained from the corresponding acid p-guanidinobenzoic acid (V) and thionyl chloride] in pyridine.
| 【1】 Fujii, S.; Uegai, Y.; Watanabe, T.; Kayama, N. (Ono Pharmaceutical Co., Ltd.); Guanidinobenzoic acid derivatives. DE 2548886; FR 2289181; GB 1472700; JP 76054530; US 4021472 . |
| 【2】 Fujii, S.; et al. (Ono Pharmaceutical Co., Ltd.); Guanidinobenzoic acid derivatives and antiplasmin agents and remedies for pancreas diseases containing the said guanidinobensolc acid derivatives. JP 52089640 . |
| 【3】 Castaner, J.; Serradell, M.N.; Hashimoto, K.; Camostat Mesylate. Drugs Fut 1985, 10, 11, 897. |
| 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) | 18430 | 2-(4-Hydroxyphenyl)acetic acid; 4-Hydroxyphenylacetic acid | 156-38-7 | C8H8O3 | 详情 | 详情 |
| (II) | 29753 | 2-bromo-N,N-dimethylacetamide | C4H8BrNO | 详情 | 详情 | |
| (III) | 29754 | 2-(dimethylamino)-2-oxoethyl 2-(4-hydroxyphenyl)acetate | C12H15NO4 | 详情 | 详情 | |
| (IV) | 29755 | 4-[[amino(imino)methyl]amino]benzoic acid | C8H9N3O2 | 详情 | 详情 | |
| (V) | 22548 | 4-[[amino(imino)methyl]amino]benzoyl chloride | C8H8ClN3O | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VI)The alkylation of succinimide (I) with 1,2-dibromoethane (II) by means of K2CO3 in refluxing butanone gives N-(2-bromoethyl)succinimide (III), which is condensed with 4-hydroxythiophenol (IV) by means of K2CO3 in refluxing ethanol to afford 4-hydroxyphenyl 2-succinimidoethyl sulfide (V). Finally, this compound is esterified with 4-guanidinobenzoyl chloride in pyridine, and treated with methanesulfonic acid in methanol.
| 【1】 Hishinuma, I.; Kawashima, H.; Kawata, T.; Miyamoto, K.; Miyazawa, S.; Nagakawa, J.; Nagaoka, J.; Nagaoka, N.; Shimomura, N.; Souda, S.; Ueda, N.; Wakabayashi, T.; Yamanaka, T. (Eisai Co., Ltd.); Guanidinobenzoic ester deriv., a process for preparing same and pharmaceutical compsns. containing same. EP 0229370; JP 1987155253; JP 1994298730; US 4801603; US 5075335 . |
| 【2】 Prous, J.; Castaner, J.; E-3123. Drugs Fut 1988, 13, 7, 613. |
| 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) | 22543 | 2,5-pyrrolidinedione | 123-56-8 | C4H5NO2 | 详情 | 详情 |
| (II) | 10252 | 1,2-Dibromoethane; Ethylene dibromide | 106-93-4 | C2H4Br2 | 详情 | 详情 |
| (III) | 22545 | 1-(2-bromoethyl)-2,5-pyrrolidinedione | C6H8BrNO2 | 详情 | 详情 | |
| (IV) | 22546 | 4-sulfanylphenol | 637-89-8 | C6H6OS | 详情 | 详情 |
| (V) | 22547 | 1-[2-[(4-hydroxyphenyl)sulfanyl]ethyl]-2,5-pyrrolidinedione | C12H13NO3S | 详情 | 详情 | |
| (VI) | 22548 | 4-[[amino(imino)methyl]amino]benzoyl chloride | C8H8ClN3O | 详情 | 详情 |