Benzylamine → N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

To a solution of 2-amino-4-methylthiazole-5-carboxylic acid (0.86 g, 5.44 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1-hydroxy-benzotriazole (0.96 g, 7.07 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (1.36 g, 7.07 mmol), N,N-diisopropylethylamine (2.46 mL, 14.14 mmol) and benzylamine (0.71 mL, 6.53 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (30 mL) and washed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (20-35% ethyl acetate in hexanes) to afford the title compound as a white solid (1.02 g, 76%): 1H NMR (300 MHz, DMSO-d6) δ 8.01 (t, J=6.0 Hz, 1H), 7.36-71.9 (m, 7H), 4.34 (d, J=6.0 Hz, 2H), 2.34 (s, 3H); MS (ES+) m/z 248.2 (M+1).

1. washwashed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL)
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was purified by column chromatography (20-35% ethyl acetate in hexanes)

ORD record

ord-b734b4c87ef14821a1be5efb88f7da66

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258160B2