Diisopropylethylamine → HCID 66851368, compound

Participants

Reaction Steps

A mixture of 5-(5-Chloro-2-methoxyphenyl)-1-isopentyl-1H-pyrazole-4-amine (573.0 mg, 1.95 mmol, 1.00 eq), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (349.9 mg, 2.145 mmol, 1.10 eq), 7-azabenzotriazol-1-yloxy-tris-(pyrrolidino)phosphonium hexafluorophosphate (1.25 g, 2.42 mmol, 1.24 eq), and N,N-diisopropylethylamine (0.95 mL, 5.5 mmol, 2.8 eq) in 5.0 mL N,N-dimethylformamide was stirred at room temperature for 12 hours. The reaction mixture was concentrated. The crude product was purified by reverse phase HPLC and lyophilized to give 105.2 mg (12.3%) of N-(5-(5-chloro-2-methoxyphenyl)-1-isopentyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=439.1; 1H NMR (400 MHz, DMSO) δ 9.50 (s, 1H), 9.32 (dd, J=7.0, 1.6, 1H), 8.73-8.57 (m, 2H), 8.01 (s, 1H), 7.60 (dd, J=8.9, 2.7, 1H), 7.48 (d, J=2.7, 1H), 7.33 (d, J=9.0, 1H), 7.27 (dd, J=7.0, 4.2, 1H), 3.97 (dq, J=16.6, 6.8, 2H), 3.84 (s, 3H), 1.54 (q, J=7.1, 2H), 1.45-1.31 (m, 1H), 0.75 (dd, J=12.0, 6.6, 6H).

Provenance & Evidence