Hydrochloric Acid → HCID 68460474, compound

Participants

Reaction Steps

A solution of methyl 2-(5-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-1H-indazol-1-yl)acetate (100 mg, 0.217 mmol) in toluene (0.5 mL) was treated with ethane-1,2-diamine (24 mg, 0.40 mmol) and Al(CH3)3 (0.2 mL, 2 M in toluene, 0.4 mmol) at 0° C. under nitrogen. Then, the reaction mixture was heated to reflux. After stirring at reflux for 16 h, the reaction mixture was diluted with H2O (20 mL) and extracted with CH2Cl2 (2×25 mL). The organics were dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH/NH4OH, 40:1:0.05 to 20:1:0.15) provided the free base. This was dissolved in ethyl acetate (0.3 mL) and treated with 1 equivalent of 1 M HCl in Et2O. The resulting mixture was filtered to provide the title compound (13.5 mg, 14%) as a yellow solid melting point (mp) 164-166° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.22 (s, 1H), 8.31 (d, J=0.7 Hz, 1H), 7.84 (d, J=8.9 Hz, 1H), 7.82 (d, J=16 Hz, 1H), 7.59 (d, J=7.6 Hz, 1H), 7.49-7.36 (m, 6H), 6.12 (dd, J=7.6, 2.7 Hz, 1H), 5.99 (d, J=2.7 Hz, 1H), 5.70 (s, 2H), 5.16 (s, 2H), 3.87 (s, 4H); ESI MS m/z 400 [M+H]+.

Provenance & Evidence