Acetic acid, azido-, ethyl ester → HCID 71280804, compound

Participants

Reaction Steps

A mixture of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-ethynylimidazo[1,2-a]pyridine-3-carboxamide (53) (20 mg, 0.046 mmol), ethyl 2-azidoacetate (5.9 mg, 0.046 mmol), CuSO4(4 μL of 0.5M aqueous solution, 0.002 mmol) and sodium ascorbate (2.8 mg, 0.014 mmol) in tBuOH/H2O (1 mL, 2:1) was stirred at room temperature overnight. Then the reaction mixture was diluted and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated to afford a residue which was dissolved in MeOH (2 mL). NaBH4(17 mg, 0.46 mmol) was added and the reaction mixture was stirred for 30 minutes. The above mixture was purified by HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (F66). 1H NMR (400 MHz, d4-MeOH) δ 9.70 (m, 1H), 8.60-8.80 (m, 2H), 8.33 (s, 1H), 8.16 (d, J=1.6 Hz, 1H), 7.96 (m, 1H), 7.85 (d, J=7.2 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 4.62 (t, J=4.8 Hz, 2H), 4.02 (t, J=4.8 Hz, 2H), 3.79 (m, 1H), 3.13 (m, 4H), 2.44 (s, 3H). MS m/z 521.1 (M+1)+.

Provenance & Evidence