[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:16][C:17](Cl)=[O:18].[CH2:20]([CH2:22][NH2:23])[OH:21]>C1COCC1>[OH:18][CH2:17][CH2:16][NH:23][CH2:22][C:20]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:21]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).
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