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【结 构 式】 
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【分子编号】62081 【品名】acetoin; 2-Butanone, 3-hydroxy-, (+-)-; 3-hydroxy-2-butanone; Acetyl methyl carbinol; 2-butanol-3-one; 3-Hydroxybutan-2-one; Dimethylketol; (R)-Acetoin; (R)-2-Acetoin; (R)-Dimethylketol; 2-acetoin; 2,3-Butanolone; Gamma-hydroxy-beta-oxobutane; ACETOIN, NATURAL; Acetoin, 85% Aqueous Soln.; Acetylmethylcarbinol, 85% Aqueous Soln.; 3-Hydroxy-2-Butanone, 85% Aqueous Soln.; Acetyl methyl carbinol, 85 wt. % solutionin water; Acetyl-methylcarbinol; Acetyl methyl carbinol pract.,; Methylacetylcarbinol; Acetylmethylcarbinol; (ACETOIN) 【CA登记号】513-86-0 |
【 分 子 式 】C4H8O2 【 分 子 量 】88.10632 【元素组成】C 54.53% H 9.15% O 36.32% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Condensation of 2,6-dibromo-4-(trifluoromethyl)aniline (VII) with acetoin (VIII), followed by heating the intermediate imine (IX) with malononitrile at 180 C gives rise to the N-aryl pyrrole (X). Acylation of aminopyrrole (X) with Ac2O provides acetamide (XI), which undergoes ring closure to the pyrrolopyrimidine (XII) in hot phosphoric acid. Chlorination of (XII) employing POCl3 furnishes aryl chloride (XIII). This is finally condensed with tetrahydropyridine (VI) to produce the title compound
| 【1】 Oshida, Y.; Kumagai, T.; Okubo, T.; Chaki, S.; Okuyama, S.; Nakazato, A.; Synthesis, SARs and biological activities of CRH1 receptor: Novel 3- or 4-carbamoyl-1,2,5,6-tetrahydropyridinopyrrolopyrimidine derivative. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 259. |
| 【2】 Okubo, T.; et al.; 4- or 5-Carbamoyl-1,2,3,6-tetrahydropyridinopyrrolopyrimidine derivative as a CRH1 receptor antagonist. Drugs Fut 2002, 27, Suppl. A. |
| 【3】 Tomisawa, K.; Kumagai, T.; Nakazato, A.; Okubo, T. (Taisho Pharmaceutical Co., Ltd.); Carbamoyl tetrahydropyridine derivs.. EP 1176146 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 60299 | 1,2,3,6-tetrahydro-4-pyridinecarboxamide | C6H10N2O | 详情 | 详情 | |
| (VII) | 62075 | 2,6-dibromo-4-(trifluoromethyl)phenylamine; 2,6-dibromo-4-(trifluoromethyl)aniline; 4-Amino-3,5-dibromobenzotrifluoride; 2,6-Dibromo-4-trifluoromethylaniline | 72678-19-4 | C7H4Br2F3N | 详情 | 详情 |
| (VIII) | 62081 | acetoin; 2-Butanone, 3-hydroxy-, (+-)-; 3-hydroxy-2-butanone; Acetyl methyl carbinol; 2-butanol-3-one; 3-Hydroxybutan-2-one; Dimethylketol; (R)-Acetoin; (R)-2-Acetoin; (R)-Dimethylketol; 2-acetoin; 2,3-Butanolone; Gamma-hydroxy-beta-oxobutane; ACETOIN, NATURAL; Acetoin, 85% Aqueous Soln.; Acetylmethylcarbinol, 85% Aqueous Soln.; 3-Hydroxy-2-Butanone, 85% Aqueous Soln.; Acetyl methyl carbinol, 85 wt. % solutionin water; Acetyl-methylcarbinol; Acetyl methyl carbinol pract.,; Methylacetylcarbinol; Acetylmethylcarbinol; (ACETOIN) | 513-86-0 | C4H8O2 | 详情 | 详情 |
| (IX) | 62076 | 3-{[2,6-dibromo-4-(trifluoromethyl)phenyl]imino}-2-butanol | C11H10Br2F3NO | 详情 | 详情 | |
| (X) | 62077 | 2-amino-1-[2,6-dibromo-4-(trifluoromethyl)phenyl]-4,5-dimethyl-1H-pyrrole-3-carbonitrile | C14H10Br2F3N3 | 详情 | 详情 | |
| (XI) | 62078 | N-{3-cyano-1-[2,6-dibromo-4-(trifluoromethyl)phenyl]-4,5-dimethyl-1H-pyrrol-2-yl}acetamide | C16H12Br2F3N3O | 详情 | 详情 | |
| (XII) | 62079 | 7-[2,6-dibromo-4-(trifluoromethyl)phenyl]-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol | C16H12Br2F3N3O | 详情 | 详情 | |
| (XIII) | 62080 | 4-chloro-7-[2,6-dibromo-4-(trifluoromethyl)phenyl]-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine | C16H11Br2ClF3N3 | 详情 | 详情 |