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【结 构 式】 
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【分子编号】43043 【品名】3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-5-olate 【CA登记号】 |
【 分 子 式 】C10H5ClN4O3 【 分 子 量 】264.62756 【元素组成】C 45.39% H 1.9% Cl 13.4% N 21.17% O 18.14% |
合成路线1
该中间体在本合成路线中的序号：(IV)Reaction of 2-nitro-5-chlorophenylhidrazyne (I) with ethyl 2-cyano-3-ethoxypropenoate (II) in EtOH and catalytic HOAc affords derivative (III), which is simultaneously hydrolyzed and cyclized to the triazine system (IV) in aqueous NaOH. Treatment of (IV) with SOCl2 followed by addition of alcohol (V) in chloroform allows obtention of the desired product.
| 【1】 Costanzo, A.; et al.; Reactivity of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions and synthesis of new 3,7 and 8-substituted pyrazole[5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands. J Heterocycl Chem 1994, 31, 1369. |
| 【2】 Costa, B.; Ciciani, G.; Costanzo, A.; Ipponi, A.; Martini, C.; Bruni, F.; Guerrini, G.; Selleri, S.; Lucacchini, A.; Aiello, M.; Benzodiazepine receptor (BZR) ligands.5. New 3-alkyloxycarbonyl-, 3-cyclo-alkyloxycarbonyl-, 3-aryloxy-carbonylderivatives of pyrazolo [5,1-c][1,2,4]benzotriazine 5-oxides: A study on the 3-ester function modification. Med Chem Res 1999, 9, 5, 322. |
| 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) | 35819 | 1-(5-chloro-2-nitrophenyl)hydrazine | C6H6ClN3O2 | 详情 | 详情 | |
| (II) | 43041 | ethyl (Z)-2-cyano-3-ethoxy-2-propenoate | 94-05-3 | C8H11NO3 | 详情 | 详情 |
| (III) | 43042 | ethyl 5-amino-1-(5-chloro-2-nitrophenyl)-1H-pyrazole-4-carboxylate | C12H11ClN4O4 | 详情 | 详情 | |
| (IV) | 43043 | 3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-5-olate | C10H5ClN4O3 | 详情 | 详情 | |
| (V) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Reaction of 2-nitro-5-chlorophenylhidrazyne (I) with ethyl 2-cyano-3-ethoxypropenoate (II) in EtOH and catalytic AcOH affords derivative (III), which is simultaneously hydrolyzed and cyclized to the triazine system (IV) in aqueous NaOH. Treatment of (IV) with SOCl2, followed by addition of alcohol (V) in chloroform, allows obtention of the desired product.
| 【1】 Costanzo, A.; et al.; Reactivity of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions and synthesis of new 3,7 and 8-substituted pyrazole[5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands. J Heterocycl Chem 1994, 31, 1369. |
| 【2】 Costa, B.; Ciciani, G.; Costanzo, A.; Ipponi, A.; Martini, C.; Bruni, F.; Guerrini, G.; Selleri, S.; Lucacchini, A.; Aiello, M.; Benzodiazepine receptor (BZR) ligands.5. New 3-alkyloxycarbonyl-, 3-cyclo-alkyloxycarbonyl-, 3-aryloxy-carbonylderivatives of pyrazolo [5,1-c][1,2,4]benzotriazine 5-oxides: A study on the 3-ester function modification. Med Chem Res 1999, 9, 5, 322. |
| 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) | 35819 | 1-(5-chloro-2-nitrophenyl)hydrazine | C6H6ClN3O2 | 详情 | 详情 | |
| (II) | 43041 | ethyl (Z)-2-cyano-3-ethoxy-2-propenoate | 94-05-3 | C8H11NO3 | 详情 | 详情 |
| (III) | 43042 | ethyl 5-amino-1-(5-chloro-2-nitrophenyl)-1H-pyrazole-4-carboxylate | C12H11ClN4O4 | 详情 | 详情 | |
| (IV) | 43043 | 3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-5-olate | C10H5ClN4O3 | 详情 | 详情 | |
| (V) | 18710 | Benzyl alcohol; Phenylmethanol | 100-51-6 | C7H8O | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The known 3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide (I) is converted into the corresponding acid chloride (II) upon treatment with SOCl2. Subsequent condensation of acid chloride (II) with 2-thienylmethanol (III) in CHCl3 in the presence of pyridine leads to the title thienylmethyl ester.
| 【1】 Costanzo, A.; Guerrini, G.; Ciciani, G.; Bruni, F.; Costagli, C.; Selleri, S.; Besnard, F.; Costa, B.; Martini, C.; Malmberg Aiello, P.; Benzodiazepine receptor ligands. 7. Synthesis and pharmacological evaluation of new 3-esters of the 8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide. 3-(2-Thienylmethoxycarbonyl) derivative: An anxioselective agent in rodents. J Med Chem 2002, 45, 26, 5710. |