【结 构 式】 |
【分子编号】56954 【品名】(2S)-1-[4-(1,3-benzothiazol-2-ylamino)phenyl]-2-(dimethylamino)-1-propanone 【CA登记号】 |
【 分 子 式 】C18H19N3OS 【 分 子 量 】325.43448 【元素组成】C 66.43% H 5.88% N 12.91% O 4.92% S 9.85% |
合成路线1
该中间体在本合成路线中的序号:(VI)The cyclization of 1,3-diphenylthiourea (I) with Br2 and HBr in water gives N-(benzothiazol-2-yl)-N-phenylamine (II), which is condensed with 2-chloropropionyl chloride (III) by means of AlCl3 in dichloromethane to yield the propiophenone (IV). The reaction of (IV) with dimethylamine in isopropanol affords the racemic alpha-(dimethylamino) propiophenone (V), which is optically resolved by means of (+)(D)-di-p-toluoyltartaric acid providing the (S)-enantiomer (VI) with a 80% ee. The reduction of (VI) with NaBH4 and NaOH in isopropanol gives the (S,S)-enantiomer (VII) with a 85% ee. Finally, this compound is condensed with CDI and imidazole to afford the target compound that is purified by crystallization in ethyl acetate up to a 99% ee.
【1】 Aelterman, W.; et al.; Conversion of the laboratory synthetic route of the N-aryl-2-benzothiazolamine R116010 to a manufacturing method. Org Process Res Dev 2001, 5, 5, 467. |
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) | 56953 | 1,3-Diphenyl-2-thiourea; 1,3-Diphenylthiourea; N,N'-Diphenylthiourea; S-Diphenylthiocarbamide; sym-Diphenylthiourea; Thiocarbanilide | 102-08-9 | C13H12N2S | 详情 | 详情 |
(II) | 46364 | N-(1,3-benzothiazol-2-yl)-N-phenylamine; N-phenyl-1,3-benzothiazol-2-amine | C13H10N2S | 详情 | 详情 | |
(III) | 12926 | 2-Chloropropanoyl chloride; 2-Chloropropionyl chloride | 7623-09-8 | C3H4Cl2O | 详情 | 详情 |
(IV) | 46365 | 1-[4-(1,3-benzothiazol-2-ylamino)phenyl]-2-chloro-1-propanone | C16H13ClN2OS | 详情 | 详情 | |
(V) | 46366 | 1-[4-(1,3-benzothiazol-2-ylamino)phenyl]-2-(dimethylamino)-1-propanone | C18H19N3OS | 详情 | 详情 | |
(VI) | 56954 | (2S)-1-[4-(1,3-benzothiazol-2-ylamino)phenyl]-2-(dimethylamino)-1-propanone | C18H19N3OS | 详情 | 详情 | |
(VII) | 46368 | (1S,2S)-1-[4-(1,3-benzothiazol-2-ylamino)phenyl]-2-(dimethylamino)-1-propanol | C18H21N3OS | 详情 | 详情 |