Acetic Acid → HCID 178482066, compound

Participants

Reaction Steps

To (2S)-2-amino-3-(4-fluorophenyl)-N-(1-methyl-3-(2-(methylamino)pyridin-4-yl)-1H-pyrazol-5-yl)propanamide (79 mg, 214 μmol) was added 1H-pyrazole-3-carbaldehyde (29 mg, 300 μmol), then DCE and dioxane were added as solvents, followed by acetic acid (13 μl, 225 μmol) and NaBH(OAc)3 (136 mg, 643 μmol). Heating was continued for 1 hr. 40 min. The reaction was concentrated and purified by reverse phase HPLC purification to afford 23.2 (27 mg, 28%) as a white solid. 1H NMR (400 MHz, MeOH) δ ppm 7.77-8.01 (m, 1H) 7.55 (br. s., 1H) 7.25 (dd, J=8.61, 5.48 Hz, 2H) 7.03 (t, J=8.80 Hz, 2H) 6.91 (dd, J=5.67, 1.37 Hz, 1H) 6.51-6.65 (m, 1H) 6.23 (d, J=1.96 Hz, 1H) 3.74-3.91 (m, 2H) 3.60-3.63 (m, 1H) 3.59 (s, 3H) 2.97-3.11 (m, 2H) 2.89 (s, 3H).

Provenance & Evidence