Synthetic Route of 175277-11-9, The chemical industry reduces the impact on the environment during synthesis 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, I believe this compound will play a more active role in future production and life.
31) 3-(tert-butyl)-N-(2-hydroxy-3-methoxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (500 mg, 2.07 mmol, 1.0 eq) in toluene (15 mL) was added 2,4-dimethoxybenzyl amine (345 mg, 2.07 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (15 mL) and then NaBH4 (157 mg, 4.14 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (0.509 mmol, 1.1 eq) in DMF (10 mL) were added the acid (84 mg, 0.463 mmol, 1.0 eq), DIEA (300 mg, 2.32 mmol, 5 eq) and HBTU (211 mg, 0.56 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aq HCl (1*20 mL), sat NaHCO3 (1*20 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product in low yield. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H24N3O3: 318.0 (M+H), Found 318.0.
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