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

To a suspension of 2-amino-4-methylthiazole-5-carboxylic acid (5.20 g, 32.90 mmol) and di-iso-propylethylamine (15.00 mL, 86.70 mmol) in N,N-dimethylformamide (40 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (8.18 g, 42.70 mmol). The resulting mixture was stirred for 30 min, then 1-hydroxybenzotriazole hydrate (5.78 g, 42.70 mmol) was added, and followed by the addition of benzylamine (4.30 mL, 39.30 mmol). The reaction mixture was stirred at ambient temperature for 2 days, then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford the title compound in 60% yield (4.90 g); 1H NMR (DMSO-d6, 300 MHz) δ 7.36-7.25 (m, 5H), 5.79 (s, br, 1H), 5.36 (s, br, 2H), 4.54 (dd, J=5.7 Hz, 2H), 2.47 (s, 3H). MS (ES+) m/z 248.4 (M+1).

1. stirringThe reaction mixture was stirred at ambient temperature for 2 days
2. washwashed with water and brine
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo
6. customThe residue was purified by column chromatography

ORD record

ord-476286ae868f46708d1dc3df5cca8daf

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541457B2