Hydrochloric Acid → HCID 78323978, compound

Participants

Reaction Conditions

Reaction Steps

5-(4-(Benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinonitrile (prepared as in Example 11) (0.800 g, 1.99 mmol) was dissolved in dioxane (3 mL), and KOH (0.892 g, 15.9 mmol) was added. The reaction mixture was heated to 100° C. for 14 h. The reaction mixture was allowed to cool and concentrated under reduced pressure to remove dioxane. The residue obtained was diluted with water (10 mL) and neutralized with dilute HCl to pH 6. The solid was filtered and air dried. The solid was purified by preparative HPLC (Condition B-67 as described in general methods) to obtain 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinic acid (0.500 g, 59.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.83 (d, J=5.6 Hz, 2H), 6.66 (t, J=5.6 Hz, 1H), 6.83 (d, J=2.8 Hz, 1H), 7.26-7.56 (m, 10H), 7.96 (d, J=2.8 Hz, 1H), 8.99 (dd, J=1.6 Hz, J=2.0 Hz, 1H), 9.14 (d, J=2.0 Hz, 1H), 9.53 (d, J=1.6 Hz, 1H), 13.61 (br s, 1H). LCMS Condition B-44: retention time 1.54 min, [M+1]=422.2. HPLC Condition B-31: retention time 10.72 min, Purity 97.70%.

Provenance & Evidence