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【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information