Diisopropylethylamine → HCID 58763927, compound

Participants

Reaction Steps

Diisopropylethylamine (209 microliters, 1.2 mmol) was added slowly via syringe to a solution of 4-(2-aminoethylamino)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid (I-4d, 228 mg, 0.53 mmol) and HATU (456 mg, 1.2 mmol) in anhydrous DMF (30 ml) at room temperature. The reaction mixture was stirred for 17 hours, diluted with saturated aqueous NaCl, and extracted with EtOAc (2×). The combined EtOAc extracts were washed with 0.5 M citric acid, 1 M K2CO3, and saturated aqueous NaCl, dried and concentrated in vacuo. The residue was slurried with CH2Cl2 and the organic solvent decanted, a process that was repeated twice. The combined organic solutions were concentrated in vacuo and the residue was purified on a chromatotron using 4 mm plates and a solvent gradient of 100% EtOAc to 10:1 EtOAC/MeOH to give I-4e as a colorless solid (82 mg): +ES MS (M+1) 373.4.

Provenance & Evidence