1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523548, compound

Participants

Reaction Steps

DIPEA (100 mg, 0.13 mL, 0.7 mmol) was added to a stirred solution of (2-Bromo-5-fluoro-phenyl)-piperazin-1-yl-methanone; hydrochloride salt (prepared by the method as described above)(68 mg, 0.21 mmol) in DMF (4 mL). HOBT (31 mg, 0.23 mmol) and EDCI (91 mg, 0.47 mmol) were then added at room temperature. After 2 minutes, {[5-(2-Hydroxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (50 mg, 0.19 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 68.5 mg (68.5% yield) 5-(2-Hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-5-fluoro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 95.24%. 1H NMR (DMSO-d6): δ 13.4-13.2 (bs, 1H), 10.4-10.2 (bs, 1H), 8.2-8.0 (bs, 1H), 7.8-7.64 (m, 2H), 7.46-7.34 (bs, 1H), 7.34-7.2 (t, 2H), 7.02-6.84 (m, 4H), 4.26-4.1 (bd, 2H), 3.76-3.46 (bt, 6H), 3.24-3.1 (bd, 2H).

Provenance & Evidence