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【结 构 式】 
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【分子编号】35788 【品名】1-(2,4-dichlorophenyl)-4-methyl-5-(2-nitrophenyl)-1H-pyrazole-3-carbonyl chloride 【CA登记号】 |
【 分 子 式 】C17H10Cl3N3O3 【 分 子 量 】410.64292 【元素组成】C 49.72% H 2.45% Cl 25.9% N 10.23% O 11.69% |
合成路线1
该中间体在本合成路线中的序号：(XIIIa)Propiophenone (IX) was condensed with diethyl oxalate to give diketone (X). Reaction with hydrazine (III) afforded pyrazole (XI). Nitration of (XI) by nitronium tetrafluoborate in acetonitrile gave a mixture of para- and ortho-nitrated compounds (XIIa-b), which were used without separation. Ester hydrolysis, followed by chlorination to (XIIIa-b) and condensation with 1-aminopiperidine (VI) gave the corresponding mixture of para- and ortho-nitro amides, which were separated by flash chromatography. The required para-isomer (XIV) was reduced by hydrazine and Raney Nickel to aniline (XV). This was finally converted to the title iodide via the reaction of the diazonium salt with NaI.
| 【1】 Fan, P.; Liu, Q.; Lan, R.; et al.; Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 1999, 42, 4, 769. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIIa) | 35786 | ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(2-nitrophenyl)-1H-pyrazole-3-carboxylate | C19H15Cl2N3O4 | 详情 | 详情 | |
| (XIIb) | 35787 | ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-nitrophenyl)-1H-pyrazole-3-carboxylate | C19H15Cl2N3O4 | 详情 | 详情 | |
| (XIIIa) | 35788 | 1-(2,4-dichlorophenyl)-4-methyl-5-(2-nitrophenyl)-1H-pyrazole-3-carbonyl chloride | C17H10Cl3N3O3 | 详情 | 详情 | |
| (XIIIb) | 35789 | 1-(2,4-dichlorophenyl)-4-methyl-5-(4-nitrophenyl)-1H-pyrazole-3-carbonyl chloride | C17H10Cl3N3O3 | 详情 | 详情 | |
| (III) | 35778 | 1-(2,4-dichlorophenyl)hydrazine | 5446-18-4 | C6H6Cl2N2 | 详情 | 详情 |
| (VI) | 35781 | 1-piperidinylamine; 1-piperidinamine | 2213-43-6 | C5H12N2 | 详情 | 详情 |
| (IX) | 33531 | propiophenone | 93-55-0 | C9H10O | 详情 | 详情 |
| (X) | 35784 | C13H13LiO4 | 详情 | 详情 | ||
| (XI) | 35785 | ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxylate | C19H16Cl2N2O2 | 详情 | 详情 | |
| (XIV) | 35790 | 1-(2,4-dichlorophenyl)-4-methyl-5-(4-nitrophenyl)-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide | C22H21Cl2N5O3 | 详情 | 详情 | |
| (XV) | 35791 | 5-(4-aminophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide | C22H23Cl2N5O | 详情 | 详情 |