반응 #45045

반응 방정식

Trifluoroacetic acid

tert-butyl 3-(3,5-dimethoxyphenethyl)-5-(4-iodobenzamido)-1H-pyrazole-1-carboxylate

→

title compound

수율 24.3%

N-[5-[2-(3,5-Dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-iodo-benzamide

수율 24.3%

용매

DCM

반응 조건

후처리

1. 1
   기타The reaction mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONredissolved in MeOH (5 mL)
3. 3
   기타The crude product was purified by ion exchange chromatography
4. 4
   세척The desired product was eluted from the column
5. 5
   기타were evaporated to dryness
6. 6
   기타to afford a tan solid
7. 7
   기타The solid was triturated with DCM

실험 절차

Trifluoroacetic acid (3.85 mL, 50.02 mmol) was added in one portion to tert-butyl 3-(3,5-dimethoxyphenethyl)-5-(4-iodobenzamido)-1H-pyrazole-1-carboxylate (288 mg, 0.5 mmol) in DCM (10 mL) at room temperature. The resulting solution was stirred for 24 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (5 mL). The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 3.5M NH3/Methanol and pure fractions were evaporated to dryness to afford a tan solid. The solid was triturated with DCM to give the title compound (58.0 mg, 24.3%) as a white solid; 1H NMR (399.9 MHz, DMSO-d6) δ 2.88 (4H, s), 3.73 (6H, s), 6.33 (1H, t), 6.42 (2H, d), 6.47 (1H, s), 7.77 (2H, d), 7.87 (2H, d), 10.73 (1H, s), 12.17 (1H, s).

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