Triethylamine → 1-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-1-oxopropan-2-yl acetate

Participants

Reaction Steps

To a stirred solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine dihydrochloride (3.00 g, 10.2 mmol) in CH2Cl2 (20 mL) cooled in an ice bath were added triethylamine (5.7 mL, 40.6 mmol) followed by dropwise addition 1-chloro-1-oxopropan-2-yl acetate (1.3 mL, 10.2 mmol). The reaction mixture was stirred overnight warming to room temperature. The reaction mixture was then diluted with CH2Cl2 and washed with water. The phases were separated, and the organics were dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with 0%-70% acetone/hexanes to afford the title compound C12 as a tan taffy-like solid (3.2 g, 93%): 1H NMR (400 MHz, CDCl3) δ 8.99 (d, J=2.5 Hz, 1H), 8.62 (dd, J=4.8, 1.3 Hz, 1H), 8.18 (s, 1H), 8.04 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.46 (ddd, J=8.4, 4.8, 0.5 Hz, 1H), 5.01 (d, J=6.5 Hz, 1H), 3.54 (m, 2H), 2.09 (s, 3H), 1.39 (d, J=6.8 Hz, 3H), 1.17 (t, J=7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 171.01, 148.62, 140.57, 140.24, 135.63, 127.56, 126.33, 124.06, 122.58, 67.49, 43.74, 20.61, 16.80, 12.57 (one carbon signal not located); ESIMS m/z 336.4 ([M+H]+), 335.0 ([M−H]−).

Provenance & Evidence