Dichloromethane → HCID 53497452, compound

Participants

Reaction Steps

3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanediamide (0.047 g, 0.12 mmol) was partially dissolved in DMF (0.3 mL) and DCM (0.5 mL) and triethylamine (0.08 g, 0.79 mmol) was added. 2,2,2-trichloroacetyl chloride (0.08 g, 0.44 mmol) was added at 0° C., and the reaction was stirred for 1 hour. Additional reagents (40 mg Et3N and 30 mg acid chloride) were added and the reaction was complete. The reaction was concentrated and pumped to dryness. A minimum amount of water was added (1.5 mL) to dissolve the crude product. Excess sodium chloride was added to the aqueous layer and this mixture was extracted with EtOAc (10×10 mL) to recover the desired product. The organic phase was dried using MgSO4 and concentrated to provide 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedinitrile (42 mg, 98% yield). MS (apci) m/z=358.1 (M+H). 1H NMR (d6-DMSO) δ 9.12 (s, 1H), 8.59 (s, 1H), 8.41 (s, 1H), 8.25 (s, 1H), 8.17 (s, 1H), 7.78 (s, 1H), 7.76 (s, 1H), 5.30-5.29 (m, 1H), 3.91 (s, 3H), 1.22-1.10 (m, 4H).

Provenance & Evidence