Ethylorthoformate → Bis-(3-methyl-pyridin-2-ylmethyl)-(1-[1,2,4]oxadiazol-3-yl-piperidine-4-yl)-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-N-hydroxy-piperidine-1-carboxamidine (50 mg, 0.13 mmol), dioxane (2 ml) and ethyl orthoformate (2 ml) were heated for 17 hours at 100° C. The volatiles were removed in vaccuo, and the residue was purified using radial chromatography on silica gel (20:1:1 CH2Cl2:MeOH:NH4OH) to provide COMPOUND 335 as a yellow oil (34.2 mg, 69%). 1H NMR (CHCl3) δ 1.70-1.82 (m, 5H), 1.96-2.00 (m, 2H), 2.10 (s, 6H), 2.68-2.86 (m, 3H), 3.83 (s, 4H), 4.08-4.13 (m, 2H), 7.09 (dd, 2H, J=5.7, 8.4 Hz), 7.37 (d, 2H, J=8.4 Hz), 8.29 (s, 1H), 8.34 (d, 2H, J=5.7 Hz); 13C NMR (CHCl3) δ 18.4, 26.7, 46.9, 55.0, 57.6, 122.8, 133.8, 138.4, 146.3, 157.6, 164.3, 169.9; ES-MS m/z 401 (M+Na). Anal. Calcd. for C21H26N6.0.2H2O.0.4CH2Cl2: C, 61.78; H, 6.59; N, 20.20. Found: C, 61.77; H, 6.59; N, 19.93.

Provenance & Evidence