Ammonium formate → HCID 86275388, compound

Participants

Reaction Conditions

Reaction Steps

4-Benzyl-N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide (0.151 g, 0.284 mmol), 10% Pd/C (50% H2O, 0.121 g, 0.057 mmol) and ammonium formate (0.054 g, 0.852 mmol) were combined in MeOH (5 mL) and stirred with heating at 70° C. After 2 h, the reaction was cooled to RT and filtered through diatomaceous earth. The cake was washed well with MeOH and the combined filtrates were concentrated to afford crude product (0.11 g). This was purified by silica gel chromatography (10% MeOH/CH2Cl2; then 0-10% 7M NH3 in MeOH/CH2Cl2) to afford N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide (66 mg; 53%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.22 (s, 1H), 10.44 (s, 1H), 9.18 (s, 1H), 8.23 (d, J=2.9 Hz, 1H), 8.11 (d, J=5.7 Hz, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.71 (dd, J=9.0, 2.9 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H), 6.61 (dd, J=5.7, 2.4 Hz, 1H), 3.33-3.31 (m, 4H), 2.63 (t, J=4.9 Hz, 4H), 2.47 (m, 1H), 1.21 (s, 9H); MS (ESI) m/z: 442.2 (M+H+).

Provenance & Evidence