4-Methylmorpholine → HCID 46945972, compound

Participants

Reaction Conditions

Reaction Steps

3-(2,4-Difluorophenyl)-1-(pyrazin-2-yl)-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (43.6 mg, 0.069 mmol, with 4 equivalents of sodium chloride), L-(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine bis-hydrochloride (17.2 mg, 0.086 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (28.5 mg, 0.149 mmol), 1-hydroxy-7-azabenzotriazole (5.2 mg, 0.038 mmol), and N-methylmorpholine (31 μl, 0.282 mmol) were dissolved in N,N-dimethylformamide (700 μl) at 25° C. The reaction mixture was heated to 50° C. and allowed to stir for 10 min. The reaction was stopped, quenched by addition of water (ca 0.2 mL) and trifluoroacetic acid (ca 0.2 mL). The reaction mixture was purified directly by preparative HPLC (Reverse phase (C-18)), eluting with acetonitrile/water 0.05% ammonium hydroxide, to give the title compound (21.5 mg, 0.046 mmol, 66.3% yield) as a white solid. HRMS [M+1] found=468.1063. 1H. NMR (500 MHz, CDCl3): δ 9.45 (s, 1H); 8.54-8.46 (m, 2H); 8.20-8.13 (m, 1H); 7.74 (d, J=3.9 Hz, 1H); 7.10-7.04 (m, 1H); 7.03-6.97 (m, 1H); 6.89 (d, J=7.8 Hz, 1H); 5.63 (t, J=7.3 Hz, 1H); 2.44 (s, 3H); 1.74 (d, J=7.1 Hz, 3H).

Provenance & Evidence