Diisopropylethylamine → HCID 178489595, compound

Participants

Reaction Steps

Amine 367 (0.095 g, 0.16 mmol), pyrazole-1-carboxamidine (60 mg, 0.41 mmol), and Hunigs base (0.07 g, 0.5 mmol) were stirred in dry DMF (10 mL) for 48 h at r.t. The mixture was then partitioned between ethyl acetate and water. The aqueous phase was collected and treated with brine; a precipitate was formed which was isolated by suction filtration. The resulting solid was re-dissolved in 1:1 dichloromethane/methanol, filtered, and the filtrate was concentrated to afford 361 as a solid (90 mg, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.71 (br s, 1H); 9.63 (br s, 1H); 8.49 (d, J=5.5, 1H); 8.10 (s, 1H); 8.05 (d, J=8.4, 1H); 7.93-7.70 (m, 2H); 7.51-7.40 (m, 5H); 7.08-7.02 (m, 3H); 6.92-6.88 (m, 1H); 6.63 (d, J=5.5, 1H); 4.13 (t, J=5.9, 2H); 3.84 (s, 3H); 3.64 (s, 2H); 1.95 (quint, J=6.3, 2H). [A triplet corresponding to 3H is hidden by the residial DMSO peak]. LRMS (M+H): 643.0.

Provenance & Evidence