Diisopropylethylamine → HCID 178433746, compound

Participants

Reaction Steps

To a mixture of 1-{3-[4-(4-chlorobenzyl)-5-(4H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-2-methylpyrazolo[1,5-a]pyridin-5-yl}methanamine (0.0250 g, 0.0553 mmol) and 1H-pyrazole-1-carboxamidine hydrochloride (8.20 mg, 0.0559 mmol) in dry N,N-dimethylformamide (0.50 mL) was added N,N-diisopropylethylamine (7.15 mg, 0.0553 mmol). The solution was stirred at rt for 23 hours. The reaction mixture was diluted with water (15 mL) and extracted with EtOAc (5×15 mL). The EtOAc solution was washed with brine, dried over Na2SO4, filtered, and concentrated in a rotary evaporator to give a crude residue. The residue was dissolved in ˜0.2 mL of MeOH, then diluted with ˜5 mL of EtOAc. The resulting solid was collected by filtration to give a pale yellow powder product (0.008 g, 30%). LCMS: (FA) ES+ 478, 480; ES− 476, 478. 1H NMR (400 MHz, CDCl3 and d4-methanol) δ: 8.25-8.27 (d, J=7.28 Hz, 1H), 8.17 (s, 1H), 7.92 (s, 1H), 7.21-7.23 (d, J=8.53 Hz, 2H), 7.08-7.10 (d, J=8.28 Hz, 2H), 6.72-6.74 (dd, J=7.28, 1.76 Hz, 1H), 4.48 (s, 2H), 4.30 (s, 2H), 2.57 (s, 3H).

Provenance & Evidence