Ethylene Glycol → HCID 71281216, compound

Participants

Reaction Conditions

Reaction Steps

N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxamide (F37) (0125 mg, 0.285 mmol) was dissolved in DCM (1 mL) and DIEA (0.854 mmol). MsCl (0.57 mmol) was added dropwise. After 15 minutes at room temperature the solvent was removed. MeOH (5 mL) and water (10 mL) were added to the residue. After sonication, most of the MeOH was removed from the mixture. Solid product was filtered and dried under vacuum to give the crude mesylate, which was used in the next step without purification. MS m/z 518.0 (M+1)+. A mixture of (3-((5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)carbamoyl)imidazo[1,2-a]pyridin-6-yl)methyl methanesulfonate (10.4 mg, 0.02 mmol) and K2CO3(8.3 mg, 0.06 mmol) in ethane-1,2-diol (0.5 mL) was heated at 80° C. for 20 minutes. The reaction mixture was purified by preparative HPLC to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(2-hydroxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (F38). 1H NMR (400 MHz, CDCl3) δ 9.56 (m, 1H), 8.60 (d, J=1.5 Hz, 1H), 8.21 (s, 1H), 7.89 (dd, J=1.7, 7.9 Hz, 1H), 7.77 (d, J=9.2 Hz, 1H), 7.60 (s, 1H), 7.50 (dd, J=1.7, 9.2 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 4.65 (s, 2H), 3.82 (s, 2H), 3.73-3.61 (m, 3H), 3.15 (m, 4H), 2.46 (s, 3H), 2.04 (s, 1H). MS m/z 484.2 (M+1)+.

Provenance & Evidence