Methylamine → HCID 59208400, compound

Participants

Reaction Steps

Triethylamine (30.6 mg, 0.30 mmol) and methanamine (0.075 mL, 0.15 mmol), (2M soln in methanol) were added to a solution of 4′-(4-ethylthiazol-2-yl)-6′-(3-ethylureido)-3,3′-bipyridine-5-carboxylic acid (Example 99, 60 mg, 0.15 mmol) in DMF (1.5 mL). The solution was stirred for 10 minutes and then 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (57.4 mg, 0.15 mmol) was added. The resulting light yellow solution was stirred at room temperature for one hour. A small aliquat was withdrawn and analyzed by LCMS. Since the reaction was not complete, one more equivalent of methylamine solution and HATU were added. The analysis and addition of methylamine and HATU was repeated 3-4 times, however, the reaction did not go to completion. It was then diluted with water and extracted with ethylacetate 2-3 times. The extract was washed with water (3 times), brine and dried over magnesium sulfate, then concentrated to give the title compound as an off-white solid, which was triturated with acetonitrile and lyophilized to remove excess solvent (15 mg). MS (ES) MH+: 411 for C20H22N6O2S; NMR: 1.08 (t, 3H); 1.11 (t, 3H); 2.64 (q, 2H); 2.79 (d, 3H); 3.17-3.22 (m, 2H); 7.40 (s, 1H); 7.66 (s, 1H); 8.12 (d, 1H); 8.16 (s, 1H); 8.28 (s, 1H); 8.55 (s, 1H); 8.68 (s, 1H); 8.99 (d, 1H); 9.02 (s, 1H); 9.44 (s, 1H).

Provenance & Evidence