With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3622-35-3,Benzo[d]thiazole-6-carboxylic acid,as a common compound, the synthetic route is as follows.
Step 1 Benzo[d]thiazole-6-carboxylic acid (0.181 g, 1.012 mmol) was dissolved in 10 mL of dichloromethane in a round bottomed flask containing a stir bar. N,N-Dimethylformamide (7.40 mg, 0.101 mmol) was added to this stirring mixture, and then the mixture was cooled to 0 C. A solution of oxalyl chloride (0.193 g, 0.132 mL, 1.518 mmol) in 3 mL of dichloromethane was added dropwise. The reaction was allowed to slowly warm to room temperature and then to further mix for one hour. The reaction was concentrated in vacuo to remove solvent and excess oxalyl chloride, while not heating over 30 C. This crude mixture was then redissolved in 2 mL of dichloromethane and added dropwise to a solution of pyridin-4-amine (0.095 g, 1.012 mmol), triethylamine (0.358 g, 0.494 mL, 3.54 mmol) in dichloromethane (2 mL) that had been previously placed in Mettler-Toledo Bohdan Miniblock reaction tube (Mettler-Toledo Autochem Reaction tubes 10.0 mi Part No.1352118) (Note: 6*4 Miniblock setups were used to generate 24 different products per block in parallel). After the addition, the septum layer and cover plate were secured onto the Miniblock with spring clamps. The block was then secured onto a Bohdan Miniblock Compact Shaking and Washing Station, in which the shaker was set at 600 rpm for 16 hours. The Miniblock was then removed from the shaker, followed by a subsequent draining of the reaction mixture into a second Miniblock containing a Biotage ISOLUTE SPE Accessories Phase Separator Tube (Part No.120-1905-CG), containing water (3 mL). A cover plate was placed on the second Miniblock containing the reaction mixture, and then the Miniblock was placed on the shaker and was allowed to shake for five minutes at 600 rpm. After removal of the Miniblock from the shaker, the organic phase was allowed to drain into a sample collection tube. Sample was concentrated in vacuo in a GeneVac HT-4X centrifugal evaporator and then purified via automated preparative reverse-phase HPLC purification (Method listed below) to give N-(pyridin-4-yl)benzo[d]thiazole-6-carboxamide (0.228 g, 88% yield)., 3622-35-3
As the paragraph descriping shows that 3622-35-3 is playing an increasingly important role.
Reference：
Patent; Seed, Patrick C.; Goller, Carlos C.; Dutta, Apurba; Maki, Brooks; Schoenen, Frank; Noah, James; White, Lucile; US2014/371194; (2014); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica