3-BROMO-4-ETHOXYBENZALDEHYDE

16) N-(3-bromo-4-ethoxybenzyl)-3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (1.0 g, 437 mmol, 1.0 eq) in toluene (25 mL) was added 2, 4-dimethoxybenzyl amine (802 mg, 4.80 mmol, 1.1 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 (25 mL) and then NaBH4 (330 mg, 8.74 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 (1.46 mmol, 1.0 eq) in DMF (15 mL) was added the acid (263 mg, 1.46 mmol, 1.0 eq), DIEA (939 mg, 1.30 mmol, 5 eq) and HBTU (662 mg, 1.75 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% aqHCl (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. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H25BrN3O2: 394.0 (M+H), Found 394.0.17) N-(3-bromo-4-ethoxybenzyl)-3-isopropyl-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (1.0 g, 437 mmol, 1.0 eq) in toluene (25 mL) was added 2, 4-dimethoxybenzyl amine (802 mg, 4.80 mmol, 1.1 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 (25 mL) and then NaBH4 (330 mg, 8.74 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 (1.46 mmol, 1.0 eq) in DMF (15 mL) was added the acid (244 mg, 1.46 mmol, 1.0 eq), DIEA (939 mg, 1.30 mmol, 5 eq) and HBTU (662 mg, 1.75 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% aqHCl (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. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H23BrN3O2: 380.0 (M+H), Found 380.0.

Molecular Weight:229.07
XLogP3:2.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:227.97859
Monoisotopic Mass:227.97859
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:150
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes