Benzylamine → HCID 45823040, compound

To a solution of 4-methylthiazole-5-carboxylic acid (5.00 g, 34.92 mmol) in anhydrous N,N-dimethylformamide (75 mL) was added 1-hydroxybenzotriazole (5.66 g, 41.91 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (8.04 g, 41.91 mmol), N,N-diisopropylethylamine (18.23 mL, 104.76 mmol) and benzylamine (4.57 mL, 41.91 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (100 mL) and washed with saturated aqueous sodium bicarbonate solution (55 mL) and brine (45 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (35-45% ethyl acetate in hexanes) to afford N-benzyl-4-methylthiazole-5-carboxamide as a white solid (4.85 g, 60%): 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H), 7.36-7.33 (m, 5H), 6.17 (br s, 1H), 4.61 (d, J=6.0 Hz, 2H), 2.72 (s, 3H); MS (ES+) m/z 233.2 (M+1).

1. washwashed with saturated aqueous sodium bicarbonate solution (55 mL) and brine (45 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 (35-45% ethyl acetate in hexanes)

ORD record

ord-14d703aa06b54ef694c0f9ada2fec5d4

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258160B2