4-Methylmorpholine → 3-(2-Chlorophenyl)-1-isopropyl-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-1H-indazole-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2-chlorophenyl)-1-isopropyl-1H-indazole-6-carboxylic acid (13.3 mg, 42.0 μmol) in N,N-dimethylformamide (0.5 mL) were added hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (10.4 mg, 63.0 μmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (16.2 mg, 85.0 μmol), 1-hydroxy-7-azabenzotriazole (2.9 mg, 21.0 μmol) and N-methylmorpholine (18.6 μL, 0.17 mmol). The mixture was heated to 50° C. and stirred for 30 min. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the bistrifluoroacetate salt of the title compound (12 mg): HRMS [M+1] found=424.1530; 1H NMR (500 MHz, CDCl3): δ 8.12 (s, 1H); 7.75 (d, J=8.4 Hz, 1H); 7.63-7.59 (m, 1H); 7.57-7.53 (m, 1H); 7.49 (d, J=8.4 Hz, 1H); 7.39 (dd, J=5.9, 3.5 Hz, 2H); 6.84 (d, J=7.7 Hz, 1H); 5.68-5.61 (m, 1H); 5.03-4.95 (m, 1H); 2.42 (s, 3H); 1.74 (d, J=7.0 Hz, 3H); 1.67 (d, J=6.6 Hz, 6H).

Provenance & Evidence