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【结 构 式】 
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【分子编号】14886 【品名】N-[2-(dimethylamino)ethyl]-N'-(2,2-dimethylpropanoyl)-N-(3-pyridinylmethyl)thiourea 【CA登记号】 |
【 分 子 式 】C16H26N4OS 【 分 子 量 】322.4748 【元素组成】C 59.59% H 8.13% N 17.37% O 4.96% S 9.94% |
合成路线1
该中间体在本合成路线中的序号：(VI)SR 27417 (N-(2-dimethylaminoethyl)-N-(3-pyridinylmethyl)[4-(2,4,6-triisopropylphenyl)thiazol-2-yl]amine difumarate) was prepared via a convergent route. Reductive amination of N,N-dimethylaminoethanamine (I) and pyridyl-3-carboxaldehyde (II) by sodium borohydride gave the amine (III). Eaction of pivaloyl chloride (IV) and potassium thiocyanate in anhydrous acetone provided the pivaloyl isothiocyanate (V), which was condensed in situ with the amine (III) to afford the protected thiourea (VI). Chlorhydric hydrolysis of (IV) gave the thiourea (VII) with the bromoketene (IX) in refluxing ethanol led to SR 27417.
| 【1】 Herbert, J.M.; Valette, G.; Bernat, A.; Savi, P.; Maffrand, J.P.; Le Fur, G.; SR 27417, a highly potent, selective and long-acting antagonist of the PAF receptor. Drugs Fut 1992, 17, 11, 1011. |
| 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) | 14881 | N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine | 108-00-9 | C4H12N2 | 详情 | 详情 |
| (II) | 12849 | Nicotinaldehyde; 3-Pyridinecarboxaldehyde | 500-22-1 | C6H5NO | 详情 | 详情 |
| (III) | 14883 | N-[2-(dimethylamino)ethyl]-N-(3-pyridinylmethyl)amine; N(1),N(1)-dimethyl-N(2)-(3-pyridinylmethyl)-1,2-ethanediamine | C10H17N3 | 详情 | 详情 | |
| (IV) | 13597 | 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride | 3282-30-2 | C5H9ClO | 详情 | 详情 |
| (V) | 14885 | 2,2-dimethylpropanoyl isothiocyanate | C6H9NOS | 详情 | 详情 | |
| (VI) | 14886 | N-[2-(dimethylamino)ethyl]-N'-(2,2-dimethylpropanoyl)-N-(3-pyridinylmethyl)thiourea | C16H26N4OS | 详情 | 详情 | |
| (VII) | 14887 | N-[2-(dimethylamino)ethyl]-N-(3-pyridinylmethyl)thiourea | C11H18N4S | 详情 | 详情 | |
| (VIII) | 14888 | 1,3,5-triisopropylbenzene | 717-74-8 | C15H24 | 详情 | 详情 |
| (IX) | 14889 | 2-bromo-1-(2,4,6-triisopropylphenyl)-1-ethanone | C17H25BrO | 详情 | 详情 |