Ethanolamine → HCID 56953206, compound

Participants

Reaction Steps

A mixture of 3,5-dichloro-4-[4-(6-chloropyrimidin-4-ylamino)-thiazolo[5,4-c]pyridin-2-yl]-benzonitrile (0.030 g, 0.07 mmol) and ethanolamine (12.6 μL, 0.21 mmol) in NMP (0.7 mL) was subjected to microwave irradiation at 150° C. for 75 minutes. Further ethanolamine (5.0 μL, 0.08 mmol) was added and the mixture subjected to microwave irradiation at 160° C. for 45 minutes then 190° C. for 45 minutes. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge that was washed with MeOH and the product eluted with 2M ammonia in MeOH. The relevant fractions were combined and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-5% MeOH in DCM) to give the desired compound as an off-white solid (0.014 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.13 (s, 1H), 8.40-8.34 (m, 3H), 8.16 (s, 1H), 7.73 (d, J=5.6 Hz, 1H), 7.22 (br s, 1H), 6.85 (br s, 1H), 4.72 (t, J=5.4 Hz, 1H), 3.52 (q, J=5.9 Hz, 3H). LCMS (Method C): RT=3.10 min, m/z: 458 [M+H+].

Provenance & Evidence