Benzylamine → HCID 43424405, compound

To a stirred solution of 5-bromo-3-thiophenecarboxylic acid (0.50 g, 2.42 mmol) in N,N-dimethylformamide (5 mL) was added N,N-diisopropylethylamine (1.30 mL, 7.46 mmol), 1-hydroxybenzotriazole (0.49 g, 3.61 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.69 g, 3.62 mmol). Benzylamine (0.26 mL, 2.41 mmol) was added 5 minutes later. The reaction mixture was stirred at ambient temperature for 16 h, then diluted with ethyl acetate (75 mL). The organic layer was washed with 10% aqueous hydrochloric acid (25 mL), saturated aqueous sodium bicarbonate (2×25 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford the title compound as a colorless solid (0.57 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=1.6 Hz, 1H), 7.37-7.31 (m, 6H), 6.14 (br s, 1H), 4.59 (d, J=5.7 Hz, 2H).

1. washThe organic layer was washed with 10% aqueous hydrochloric acid (25 mL), saturated aqueous sodium bicarbonate (2×25 mL)
2. dry with materialdried over sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-881592fd5880443983ed26ef08d481e0

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501746B2