With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.204512-95-8,(S)-Tetrahydrofuran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.
Example 241: (S)-l-(5-chloro-6-methyl-l-p-tolyl-lH-benzo[d]imidazol-2-yl)-7V- (tetrahydrofuran-3-yl)piperidine-4-carboxamideA tautomeric mixture of ethyl l-(6-chloro-5-methyl-lH-benzo[d]imidazol-2-yl)piperidine-4- carboxylate and ethyl l-(5-chloro-6-methyl-lH-benzo[d]imidazol-2-yl)piperidine-4-carboxylate (80.5 mg, 0.25 mmol) dimethylsulfoxide (0.5 mL), caesium carbonate (114 mg, 0.35 mmol), 1- iodo-4-methylbenzene (109 mg, 0.50 mmol), 8-hydroxyquinoline (7.3 mg, 0.05 mmol), polyethylene glycol 400 (60.4 mg, 0.515 mmol) and copper(I) oxide (3.6 mg, 0.025 mmol) was heated at 15O0C for 4 hours. The temperature was lowered to 9O0C and water (0.004 mL) was added to the reaction mixture, which was stirred for one hour. Aqueous sodium hydroxide (0.5 mL, 1 N) and ethanol (1 mL) was added and the reaction mixture stirred over night. Aqueous hydrochloric acid (0.25 mL, 2 N) was added and the reaction mixture concentrated in vacuo. The residue was mixed with N,N-dimethylformamide (5 mL), JV,jV-diisopropylethylamine (Hunig’s base, DIEA, 97 mg, 0.75 mmol), 2-(7-aza-lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium hexafluoro-phosphate (EtaATU, 114 mg, 0.3 mmol) and (S)-tetrahydrofuran-3 -aminehydrochloride (31 mg, 0.25 mmol). The reaction mixture was stirred at room temperature for 90 minutes, concentrated in vacuo and purified on column (silica gel, dichloromethane/methanol 96:4) to give 4.6 mg (4 % yield) of (S)-l-(5-chloro-6-methyl-l-p-tolyl-lH-benzo[d]imidazol-2- yl)-N-(tetrahydrofuran-3-yl)piperidine-4-carboxamide. LC-MS (m/z) 452.9 (M+l). Also eluting from the column was the other regioisomer (S)-l-(6-chloro-5-methyl-l-p-tolyl-lH- benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4-carboxamide.
204512-95-8, 204512-95-8 (S)-Tetrahydrofuran-3-amine hydrochloride 18664284, aTetrahydrofurans compound, is more and more widely used in various fields.
Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; STENBERG, Patric; WESTMAN, Jacob; WALLBERG, Hans; WO2011/23812; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem