Diisopropylethylamine → HCID 46221270, compound

Participants

Reaction Steps

6-methyl-3-(1H-pyrazol-1-yl)-2-pyridinecarboxylic acid D38 (24.63 mg) was dissolved in 1 ml of DMF, then TBTU (46.0 mg, 0.143 mmol) and DIPEA (0.025 ml, 0.143 mmol) were added. The suspension was stirred for 30 minutes at room temperature. N-[(1S,4S,6S)-3-azabicyclo[4.1.0]hept-4-ylmethyl]-5-(trifluoromethyl)-2-pyrazinamine D31 (30 mg) dissolved in 1 ml of DMF was added and the reaction was stirred overnight at room temperature. NaHCO3 saturated solution were added, and the aqueous layer was extracted with of DCM. The organic layers were collected together, dried through a phase separator and concentrated under vacuum to give a crude which was purified by SCX chromatography (column size 5 g). A second purification was performed by silica —NH chromatography (Biotage SP—column size 11 g, using Cy:EtOAc=5:5 to EtOAc). It was recovered the title compound E5 (22 mg). UPLC: (Acid Final_QC): rt=0.81 and 0.85 minutes (rotamers present), peaks observed: 458 (M+1). C22H22F3N7O requires 457. 1H NMR (400 MHz, CDCl3) δ ppm 8.29 (s, 1 H), 7.85-7.77 (m, 3 H), 7.52 (s, 1 H), 7.38-7.32 (m, 1 H), 7.05-6.89 (m, 1 H) 6.35-6.30 (m, 1 H) 4.58-4.37 (m, 1 H), 3.77-3.66 (m, 1 H), 3.65-3.37 (m, 2 H), 2.65 (s, 3 H), 2.50-2.36 (m, 2 H), 1.42-0.83 (m, 3 H), 0.82-0.71 (m, 1 H), 0.15-0.06 (m, 1 H).

Provenance & Evidence