1,3-Propanediamine, N1,N1,N3-trimethyl- → N,N,N'-Trimethyl-N'-[2-(5-phenyl-thiazol-2-ylamino)-pyridin-4-ylmethyl]-propane-1,3-diamine

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Reaction Steps

(4-Chloromethyl-pyridin-2-yl)-(5-phenyl-thiazol-2-yl)-amine 8-8 (0.050 g, 0.166 mmol) was dissolved in 0.50 mL DMSO. N,N,N′-trimethyl-1,3-propanediamine was added and the reaction was stirred at RT. After 1 h a copious amount precipitate had formed. Saturated NaHCO3 (aq) was added and the resulting precipitate was filtered and washed with water to afford pure compound 8-9. 1H NMR (CDCl3) δ9.16 (bs, 1H), 8.31 (d, 1H, J=5.1 Hz), 7.63 (s, 1H), 7.59 (d, 2H, J=7.4 Hz), 7.38 (t, 2H, J=7.6 Hz), 7.26 (overlapping with CHCl3), 6.91 (s, 1H), 6.88 (d, 1H, J=5.1 Hz), 3.49 (s, 2H), 2.43 (t, 2H, J=7.4 Hz), 2.30 (t, 2H, J=7.5 Hz), 2.34 (s, 3H), 2.21 (s, 6H), 1.68 (overlapping with water). MS [M+H]+382.3. mp 190-193.

Provenance & Evidence