With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-74-6,2-Chloro-6-fluorobenzo[d]thiazole,as a common compound, the synthetic route is as follows.
General procedure: Examples 103 and 104: N-i4,4-Difluoro-2-r(6-fluoro-l,3-benzothiazol-2- yl)amino]cyclopentyl}-2-(2 -l,2,3-triazol-2-yl)benzamide To a solution of N-(2-amino-4,4-difluorocyclopentyl)-2-(2H-l,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 28; 120 mg, 0.349 mmol) in dry DMSO (1.2 ml) was added 2-chloro-6-fluoro-l,3-benzothiazole (CAS number 399-74-6; 72 mg, 0.384 mmol) and DIPEA (183 mu, 1.047 mmol). The reaction was sealed and stirred at 140 C in a sand bath for 17 hours. The reaction was partitioned between ethyl acetate and water, washing with water, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was then purified by column chromatography (basic silica, 0-100 % ethyl acetate / petrol). The racemic mixture was then purified by SFC to give two enantiomers (Enantiomer 1/Example 103 and Enantiomer 2/Example 104) of the title compound.Example 103 (Enantiomer 1)1H NMR (400 MHz, OCM-d2) delta ppm 2.02 – 2.28 (m, 2 H), 2.72 – 2.98 (m, 2 H), 4.19 – 4.43 (m, 2 H), 6.91 – 7.14 (m, 1 H), 7.20 – 7.35 (m, 3 H), 7.36 – 7.42 (m, 1 H), 7.44 – 7.51 (m, 1 H), 7.52 – 7.60 (m, 1 H), 7.67 (s, 2 H), 7.74 – 7.84 (m, 1 H) MS ES+: 459Example 104 (Enantiomer 2)1H NMR (400 MHz, OCM-d2) delta ppm 2.02 – 2.28 (m, 2 H), 2.72 – 2.98 (m, 2 H), 4.19 – 4.43 (m, 2 H), 6.91 – 7.14 (m, 1 H), 7.20 – 7.35 (m, 3 H), 7.36 – 7.42 (m, 1 H), 7.44 – 7.51 (m, 1 H), 7.52 – 7.60 (m, 1 H), 7.67 (s, 2 H), 7.74 – 7.84 (m, 1 H)MS ES+: 459, 399-74-6
399-74-6 2-Chloro-6-fluorobenzo[d]thiazole 2049870, athiazole compound, is more and more widely used in various.
Reference£º
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica