Triethylamine → 2,6-Diamino-N-(5-(4-fluoro-phenoxy)-furan-2-ylmethyl)-nicotinamide

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.15 g, 0.98 mmol), triethylamine (0.41 mL, 2.94 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.65 g, 1.47 mmol) were dissolved in N,N-dimethylformamide (5 mL), and the solution was stirred at room temperature for 10 minutes. Then, a solution of C-(5-(4-fluoro-phenoxy)-furan-2-yl)methylamine described in Preparation Example 169 (304 mg, 1.47 mmol) in N,N-dimethylformamide (1 mL) was added thereto, followed by stirring at room temperature for 14 hours 50 minutes. After the reaction was completed, reaction solution was poured into brine, the solution was extracted with ethyl acetate, the fractionated organic layer was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was subjected to silica gel column chromatography, eluted with solvent (ethyl acetate), and the title compound (0.12 g, 0.35 mmol, 36%) was obtained.

1. additionwas added
2. stirringby stirring at room temperature for 14 hours 50 minutes
3. customreaction solution
4. extractionthe solution was extracted with ethyl acetate
5. dry with materialthe fractionated organic layer was dried over anhydrous magnesium sulfate
6. concentrationconcentrated
7. washeluted with solvent (ethyl acetate)

ORD record

ord-4d9dd0481b54444990869dc54ab02308

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932272B2