Triethylamine → HCID 71272332, compound

Participants

Reaction Steps

To the solution of 5-((2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-ylamino)methyl)-1,3,4-thiadiazole-2-carboxamide (17-11) (116 mg, 0.15 mmol) in THF was added NEt3 (0.1 mL, 0.7037 mmol) and TFAA (74 mg, 0.35 mmol) at 0° C. The mixture was brought to rt and stirred for 1 h. Then it was concentrated under reduced pressure and purified on silica gel (eluent PE/EA/NEt3=10/1/1%-5/1/1%) to give the product as a pale red solid (40 mg, 70%). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.38 (dd, J=7.9, 1.7 Hz, 1H), 7.04 (d, J=7.9 Hz, 1H), 5.62 (s, 1H), 5.37 (t, J=5.9 Hz, 1H), 5.05 (d, J=6.2 Hz, 2H), 4.29 (ddd, J=27.7, 11.2, 7.0 Hz, 2H), 2.49 (s, 3H), 2.28 (s, 3H), 2.16-2.03 (m, 1H), 1.96-1.70 (m, 1H), 1.41-1.17 (m, 1H), 1.17-0.94 (m, 1H); LRMS (ESI) calculated M+H for C19H20N7OS: 394.4. Found: 394.1.

Provenance & Evidence