Diisopropylethylamine → HCID 11429871, compound

Participants

Reaction Steps

Diisopropylethylamine (250 microliters, 2 mmol) was added to a mixture of 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-[(pyrrolidin-2-ylmethyl)-amino]-1H-pyrazole-3-carboxylic acid (I-5b, 160 mg, 0.37 mmol) and HATU (380 mg, 1 mmol) in DMF (50 ml) at room temperature. The reaction mixture was stirred for 5 hours, quenched with saturated aqueous NaCl, and extracted twice with EtOAc. The combined organic 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 in CH2Cl2 and the solvent decanted, a process repeated once more with EtOAc. The combined organic solutions were concentrated under vacuum and the residue was purified on a chromatogram using 4 mm plates and a solvent gradient of 10:1 EtOAc/MeOH to 5:1 EtOAc/MeOH to give 4A-1 as a white solid (46 mg): +ES MS (M+1) 413.4; 1H NMR (CD3OD) δ 7.58 (bs, 1H), 7.52–7.44 (m, 3H), 7.34 (d, 2H, J=7.6 Hz), 7.22 (d, 2H, J=7.6 Hz), 3.93–3.82 (m, 2H), 3.64–3.50 (m, 2H), 3.10–2.99 (m,1 H), 2.38–2.29 (m,1 H), 2.04–1.96 (m, 1H), 1.95–1.74 (m, 2H).

Provenance & Evidence