4,5-disubstituted thiazole derivative, preparation method and use thereof
A di-substituted and mono-substituted technology, applied in the field of diabetes-related drugs, can solve problems such as undiscovered weight gain
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0036] 5-Bromo-2-(2-chloroacetyl)aminothiazole (III-1)
[0037]
[0038] In a 100mL round bottom flask, add 1.79g (10mmol) compound II-1, 1.01g (13mmol) dry triethylamine and 50mL dry CH 2 Cl 2 , the mixture was cooled with an ice-water bath under stirring, and then slowly added dropwise 1.24 g (11 mmol) of chloroacetyl chloride dissolved in 5 mL of dry CH 2 Cl 2 After the resulting solution was added dropwise, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with 50 mL CH 2 Cl 2 After dilution, it was washed with saturated brine, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was removed on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a pure product of compound III-1, 2.30 g, with a yield of 90%. Colorless crystal, melting point 203-204°C, 1 H NMR (DMSO-d 6, 400MHz), δ12.74(s, 1H), 7.60(s, 1H), 4.40(s, 2H).
[0039] Compounds II-1 ...
Embodiment 2
[0041] 5-Bromo-2-(2-chloroacetyl)amino-4-methylthiazole (III-2)
[0042]
[0043] In a 100mL round bottom flask, add 1.93g (10mmol) compound II-2, 1.07g (13mmol) dry 2,6-lutidine and 50mL dry CH 2 Cl 2 , the mixture was cooled with an ice-water bath under stirring, and then slowly added dropwise 1.24 g (11 mmol) of chloroacetyl chloride dissolved in 5 mL of dry CH 2 Cl 2 After the resulting solution was added dropwise, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with 50 mL CH 2 Cl 2 After dilution, it was washed with saturated brine, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was removed on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a pure product of compound III-2, 2.45 g, with a yield of 91%. Colorless crystals, IR(KBr), 3332, 1690cm -1 .
[0044] Compounds II-2 and III-2 are one of the compounds having the general formu...
Embodiment 3
[0046] 2-(2-Chloroacetyl)amino-5-methylthiazole (III-3)
[0047]
[0048] In a 100mL round bottom flask, add 1.14g (10mmol) compound II-3, 1.03g (13mmol) dry pyridine and 50mL dry CH 2 Cl 2 , the mixture was cooled with an ice-water bath under stirring, and then slowly added dropwise 1.24 g (11 mmol) of chloroacetyl chloride dissolved in 5 mL of dry CH 2 Cl 2 After the resulting solution was added dropwise, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with 50 mL CH 2 Cl 2 After dilution, it was washed with saturated brine, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was removed on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain the pure product of compound III-3, 1.79 g, with a yield of 94%. Colorless crystals, melting point 96-98°C, 1 H NMR (DMSO-d 6 , 400MHz), δ6.58 (bs, 2H, NH 2 ), 6.556-6.559 (d, 1H, J=1.2Hz, Ar-H), 2.16-2.1...
PUM
| Property | Measurement | Unit |
|---|---|---|
| melting point | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More