Glycosidase inhibitors
A compound and general formula technology, applied in the direction of medical preparations containing active ingredients, biochemical equipment and methods, instruments, etc., can solve problems such as complex phenotypes
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Embodiment 1
[0316] Example 1: Preparation of 5-((4-phenylpiperidin-1-yl)methyl)thiazol-2-amine (intermediate)
[0317]
[0318] Step 1: To a solution of ethyl 2-((tert-butoxycarbonyl)amino)thiazole-5-carboxylate (5 g, 0.0183 mol) in dry THF (80 mL) was added LiAlH dropwise with stirring at 0 °C under nitrogen atmosphere 4 (15 mL, 0.0309 mol, 2.0 M solution in THF). The reaction mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction mixture was cooled to between -10°C and 0°C. The reaction was quenched by dropwise addition of 10% NaOH (5 mL). After 10 minutes, the mixture was filtered through celite and the filtrate was concentrated under reduced pressure to give crude tert-butyl (5-(hydroxymethyl)thiazol-2-yl)carbamate (6 g) as a pale yellow solid. The crude product was used in the next reaction without purification. LC / MS: (Method A) 231.0 (M+H).
[0319] 1 HNMR (DMSO-d 6 , 400MHz): δ6.78(s, 1H), 4.38(s, 2H), 1.38(s, 9H).
[0320] St...
Embodiment 1-3
[0325] Example 1-3: Preparation of N-(5-((4-phenylpiperidin-1-yl)methyl)thiazol-2-yl)propionamide
[0326] To a stirred solution of 5-((4-phenylpiperidin-1-yl)methyl)thiazol-2-amine hydrochloride (100 mg, 1 eq.) in dichloromethane (5 mL) was added propionyl chloride ( 29mg, 1eq.) and triethylamine (96mg, 3eq.). The reaction mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure, water was added, and the product was extracted with dichloromethane. The organic phase was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford N-(5-((4-phenylpiperidin-1-yl)methyl)thiazol-2-yl)propanamide trifluoroacetate as an off-white solid. Yield: 35% (41 mg). LC / MS: (Method A) 330.2 (M+H). HPLC: (Method A) Retention time: 3.03 min, 98.9%, (Max), 96.9% (254nm).
[0327] 1 HNMR (400MHz, DMSO-d 6 ): δ11.9(s, 1H)...
Embodiment 1-7
[0328] Example 1-7: Preparation of 2-methyl-5-((4-phenylpiperidin-1-yl)methyl)thiazole
[0329] Step 1: To a solution of ethyl 2-methylthiazole-5-carboxylate (1 eq) in dry THF (5 mL) was added LiAlH dropwise with stirring at 0 °C under nitrogen atmosphere 4 (1.1 eq., 2.0 M solution in THF). The reaction mixture was stirred at room temperature for 1 hour. The progress of the reaction was monitored by TLC. After the reaction was completed, the reaction mixture was cooled to between -10°C and 0°C. The reaction was quenched by dropwise addition of 10% NaOH (5 mL). After stirring for 10 minutes, the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to give (2-methylthiazol-5-yl)methanol (6 g) as a pale yellow solid. The crude product was used in the next reaction without purification. LC / MS: (Method A) 130.0 (M+H).
[0330] 1 HNMR (DMSO-d 6 , 400MHz): δ7.4(s, 1H), 5.5(s, 1H), 4.6(d, J=4.0Hz, 2H), 2.6(s, 3H).
[0331] Step 2: To a s...
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