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【结 构 式】 
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【分子编号】19676 【品名】N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5-chloro-3-iodo-2-methoxybenzamide 【CA登记号】 |
【 分 子 式 】C15H18ClIN2O2 【 分 子 量 】420.67737 【元素组成】C 42.83% H 4.31% Cl 8.43% I 30.17% N 6.66% O 7.61% |
合成路线1
该中间体在本合成路线中的序号：(IX)5-Chlorosalicylic acid (I) was esterified to ester (II) by refluxing in MeOH in the presence of H2SO4. Iodination of methyl ester (II) was performed by treatment with chloramine-T (III) and NaI in DMF to afford methyl 5-chloro-3-iodosalicylate (IV). Subsequent methylation of (IV) with dimethyl sulfate and K2CO3 in refluxing acetone gave methyl ether (V), which was then saponified with NaOH in aqueous EtOH. The resulting carboxylic acid (VI), after conversion to the corresponding acid chloride (VII) by treatment with SOCl2, was coupled with (S)-3-aminoquinuclidine (VIII) in acetonitrile to furnish unlabeled compound (IX). Treatment with bis(tri-n-butyltin) in the presence of Pd(PPh3)4 in refluxing Et3N afforded the tributylstannyl derivative (X), which was then iodinated with chloramine-T (III) in the presence of 125INa to yield the labeled product.
| 【1】 Mason, N.S.; et al.; Labeling of (S)-des-4-amino-3-[125I]iodozacopride (DAIZAC), a high-affinity radioligand for the 5-HT-3 receptor. J Label Compd Radiopharm 1996, 38, 11, 955. |
| 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) | 13895 | 5-Chloro-2-hydroxybenzoic acid; 5-Chlorosalicylic acid | 321-14-2 | C7H5ClO3 | 详情 | 详情 |
| (II) | 13714 | Methyl 5-chloro-2-hydroxybenzoate; Methyl 5-chlorosalicylate | 4068-78-4 | C8H7ClO3 | 详情 | 详情 |
| (III) | 19670 | Chloramine T | 127-65-1 | C7H7ClNNaO2S | 详情 | 详情 |
| (IV) | 19671 | methyl 5-chloro-2-hydroxy-3-iodobenzoate | C8H6ClIO3 | 详情 | 详情 | |
| (V) | 19672 | methyl 5-chloro-3-iodo-2-methoxybenzoate | C9H8ClIO3 | 详情 | 详情 | |
| (VI) | 19673 | 5-chloro-3-iodo-2-methoxybenzoic acid | C8H6ClIO3 | 详情 | 详情 | |
| (VII) | 19674 | 5-chloro-3-iodo-2-methoxybenzoyl chloride | C8H5Cl2IO2 | 详情 | 详情 | |
| (VIII) | 16984 | (3S)-1-azabicyclo[2.2.2]octan-3-amine; 1-aza-Bicyclo[2.2.2]oct-3-ylamine; (3S)-1-azabicyclo[2.2.2]oct-3-ylamine | 120570-05-0 | C7H14N2 | 详情 | 详情 |
| (IX) | 19676 | N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5-chloro-3-iodo-2-methoxybenzamide | C15H18ClIN2O2 | 详情 | 详情 | |
| (X) | 19677 | N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5-chloro-2-methoxy-3-(tributylstannyl)benzamide | C27H45ClN2O2Sn | 详情 | 详情 |