반응 #1886581

반응 방정식

1-(4-bromophenyl)-5-cyclopropyl-pyrazole-4-carboxylic acid

oxalyl chloride

cyclohexylamine

DIPEA

Intermediate #30

1-(4-bromophenyl)-5-cyclopropyl-pyrazole-4-carboxylic acid

→

1-(4-bromophenyl)-N-cyclohexyl-5-cyclopropyl-pyrazole-4-carboxamide

용매

DCM

DCM

water

반응 조건

후처리

1. 1
   기타evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONto dissolved in DCM (5 mL)
3. 3
   workup.STIRRINGThe mixture was stirred at ambient for 24 h
4. 4
   기타separating
5. 5
   여과filter
6. 6
   기타The product was recovered from the filtrate by flash column chromatography (SiO2, elution gradient 0-100% EtOAc in isohexane)
7. 7
   기타evaporated

실험 절차

1-(4-bromophenyl)-5-cyclopropyl-pyrazole-4-carboxylic acid (Intermediate #30) (237 mg, 0.77 mmol) was suspended in DCM (5 mL). One drop of DMF was added and then oxalyl chloride (200 μL, 2.32 mmol) was added slowly. The reaction mixture was stirred at ambient temperature for 4 h and then evaporated under reduced pressure. The residue was to dissolved in DCM (5 mL) and added to a solution of cyclohexylamine (97 μL, 0.85 mmol) and DIPEA (403 μL, 2.32 mmol) in DCM (5 mL). The mixture was stirred at ambient for 24 h and then water, (10 mL) was added and the mixture passed through a phase separating filter. The product was recovered from the filtrate by flash column chromatography (SiO2, elution gradient 0-100% EtOAc in isohexane). Pure fractions were combined and evaporated to give 1-(4-bromophenyl)-N-cyclohexyl-5-cyclopropyl-pyrazole-4-carboxamide as white solid. (277 mg, 92%)

출처