Diisopropylethylamine → HCID 136237294, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound [4-(pyridine-2-carbonyl)-piperidin-1-yl]-acetic acid (178 mg, 0.72 mmol) and 2-[(cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (169 mg, 0.72 mmol) in DMF (5 mL) and DCM (5 mL) at 0° C. is added DIPEA (0.50 mL, 2.87 mmol) and then HATU (313 mg, 0.82 mmol). The reaction is then stirred at 25° C. for 36 hours. The solvent was removed under vacuum and then solubilized in methanol and filtered. The compound was then purified by reverse phase using sunfire C18 ODB using water acetonitrile and TFA as a buffer to afford the title compound (140 mg). 1H NMR (400 MHz, MeOD) δ: 8.68 (s, 1H), 7.99 (m, 2H), 7.59 (s, 1H), 4.68 (s, 1H), 4.57 (s, 2H), 4.49 (s, 1H), 3.97 (t, J=5.6 Hz, 3H), 3.51 (d, J=7.1 Hz, 1H), 3.40 (s, 2H), 3.36 (s, 2H), 3.35-3.31 (m, 2H), 3.30 (d, J=11.6 Hz, 2H), 2.68-2.58 (m, 2H), 2.37-2.24 (m, 2H), 1.96-1.91 (m, 2H), 1.13-0.97 (m, 1H), 0.62-0.45 (m, 2H), 0.33-0.22 (m, 2H). HRMS calculated for C25H31N5O4=465, 2376. found (ESI, [M+H]+), 465, 2369. LRMS m/z: ES+=466.0 (M+H), retention time 1.04.

Provenance & Evidence