Diisopropylethylamine → HCID 90024952, compound

Participants

Reaction Steps

To a suspension of 2-((6-methyl-4-(piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile mono-TFA salt (33.8 mg, 0.0830 mmol) in anhydrous THF (0.8 mL) was added N,N-diisopropylethylamine (24 μL, 0.17 mmol) followed by 3-oxetanone (8.0 μL, 0.12 mmol) and the mixture was stirred for 15 min before the introduction of sodium triacetoxyborohydride (55 mg, 0.25 mmol). After stirring for a further 17 hr, the mixture was diluted with CH2Cl2 and washed with sat. aq. NaHCO3 and the organics were dried over MgSO4 and concentrated to dryness. The residue thus obtained was purified by RPLC to afford 2-((6-methyl-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile as a colorless solid (9.5 mg, 34%); 1H NMR (400 MHz, DMSO) δ 9.99 (br s, 1H), 8.44 (d, J=5.1 Hz, 1H), 8.18 (s, 1H), 7.36 (s, 1H), 7.21 (d, J=5.1 Hz, 1H), 6.75 (s, 1H), 4.54 (dd, J=6.5, 6.5 Hz, 2H), 4.45 (dd, J=6.5, 6.5 Hz, 2H), 3.42 (m, 1H), 2.80 (m, 2H), 2.44 (m, 1H), 2.40 (s, 3H), 1.86 (m, 2H), 1.76 (m, 2H), 1.63 (m, 2H); ESI-LRMS m/z [M+1]+=350.

Provenance & Evidence