Ethanolamine → 2-[(2-Hydroxyethyl)amino]-N-3-pyridinylacetamide

Temperature

60 °C

To a stirred solution of 3-aminopyridine (2.0 g, 21 mmol) and triethylamine (4 mL, 29 mmol) in THF (25 mL) under an inert atmosphere and precooled to 0–5° C., was added chloroacetyl chloride (2.2 mL, 26 mmol) dropwise over 10 min. After a further 15 min. the mixture was allowed to return to ambient temperature. Ethanolamine (5.4 mL, 87 mmol) was added and the dark solution warmed to 60° C. for 3 h. Solvents were removed in vacuo and DCM:MeOH (80:20) added to the resultant residue. This was filtered directly onto a column of silica gel, eluting with DCM:MeOH (90:10) to afford the title compound (1.3 g, 32%) isolated as an oil. 1H NMR (400 MHz, d6-DMSO) δ 2.67 (2H, t, J=5.5 Hz), 3.32 (1H, br s), 3.40 (2H, s), 3.50 (2H, t, J=5.4 Hz), 4.70 (1H, br s), 7.33–7.37 (1H, m), 8.06–8.10(1H, m), 8.26–8.28 (1H, m), 8.77–8.79 (1H, m), 10.20 (1H, br s). MS (ES+) 196 (M+1).

1. customprecooled to 0–5° C.
2. customto return to ambient temperature
3. customSolvents were removed in vacuo and DCM:MeOH (80:20)
4. additionadded to the resultant residue
5. filtrationThis was filtered directly onto a column of silica gel
6. washeluting with DCM:MeOH (90:10)

ORD record

ord-f88f5d43f5e74201b8ea926f073f525e

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144887B2