Hydrochloric Acid → HCID 178426400, compound

Participants

Reaction Steps

Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50.0 mg, 0.156 mmol), (S)—N,N-dimethylpyrrolidin-3-amine (26.7 mg, 0.234 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (44.9 mg, 0.234 mmol) in DMF (1561 μl). HOBT (35.9 mg, 0.234 mmol) and DIPEA (136 μl, 0.781 mmol) were added. The reaction was allowed to stir overnight. Then 1N aqueous hydrochloric acid (21 ML) was added and reaction mixture was then purified using preparative HPLC eluting with 0.1% formic acid in water and 5-30% acetonitrile to give the title compound (30 mg, 0.072 mmol, 46.1%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.78-1.88 (m, 1 H) 2.24 (br. s., 3 H) 2.36 (br. s., 3 H) 2.42 (s, 3 H) 2.88-3.05 (m, 2 H) 3.59-3.81 (m, 4 H) 7.58 (d, J=7.83 Hz, 1 H) 7.64 (s, 1 H) 7.95 (d, J=7.83 Hz, 1 H) 8.01 (s, 1 H) 8.11 (d, J=9.09 Hz, 1 H) 8.43 (d, J=8.84 Hz, 1 H) 8.62 (s, 1 H); ESI-MS m/z (M+H)+ calc'd for C23H24N6O2, 417.20; found 417.5.

Provenance & Evidence