تفاعل #45045

معادلة التفاعل

Trifluoroacetic acid

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

→

title compound

المردود 24.3%

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

المردود 24.3%

المذيبات

DCM

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر