Trifluoroacetic acid → HCID 71543584, compound

Participants

Reaction Conditions

Reaction Steps

6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (100 mg, 0.258 mmol) was dissolved in 1,4-dioxane (2.6 mL) followed by addition of cesium carbonate (336 mg, 1.031 mmol). After degassing with nitrogen for 5 min, Xantphos (44.8 mg, 0.077 mmol) was added. The mixture was degassed for 2 min, Pd2(dba)3 (35.4 mg, 0.039 mmol) was added, and then degassed for 1 min. Cyclopropanamine (0.090 mL, 1.289 mmol) was added and the contents sealed. The suspension was stirred for 3 h at 100° C. (heat block). The reaction mixture was poured onto water and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to a solid residue. The aq. layer was extracted with 10% MeOH/DCM (2×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford a solid. The combined solid residues were dissolved in DMSO and acetonitrile spiked with TFA, and purified by reverse phase HPLC (Gradient B: 10-70%. A: Water+0.1% TFA. B: CH3CN+0.1% TFA) The title compound was collected as 11 mg (10%); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.39-0.47 (m, 2 H), 0.68-0.76 (m, 2 H), 1.39 (d, J=6.57 Hz, 6 H), 2.11 (s, 3 H), 2.24 (s, 3 H), 2.20 (s, 3 H), 2.64-2.72 (m, 1 H), 4.30 (d, J=4.80 Hz, 2 H), 4.89 (quin, J=6.69 Hz, 1 H), 5.86 (s, 1 H), 6.34 (s, 1 H), 7.25 (d, J=3.03 Hz, 1 H), 8.41 (t, J=4.93 Hz, 1 H), 11.49 (s, 1 H). LCMS(ES) [M+H]+ 409.1

Provenance & Evidence