Hydrochloric Acid → HCID 78324891, compound

Participants

Reaction Steps

2-(5-Aminopyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (0.100 g, 0.254 mmol) (prepared as in Example 3) was dissolved in CH2Cl2 (10 mL) and chlorosulfonyl isocyanate (0.0330 mL, 0.381 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. Concentrated hydrochloric acid was added until the reaction mixture forms a clear solution. The aqueous mixture was extracted with CH2Cl2 (30 mL) and the organic layer was separated. The aqueous layer was adjusted to pH 11 using saturated solution of sodium hydroxide. The aqueous solution was extracted with CH2Cl2 (20×3 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Condition B-62 as described in general methods) to obtain 1-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)urea (30.0 mg, 27.0%). LCMS Condition B-14: retention time 1.831 min, [M+1]=437.2. HPLC Condition B-30: retention time 5.48 min, Purity 95.9%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.91 (d, J=4.8 Hz, 2H), 6.05 (br s, 2H), 6.81 (d, J=2.4 Hz, 1H), 7.27 (t, J=4.8 Hz, 2H), 7.46-7.61 (m, 7H), 7.76 (dt, J=1.6 Hz, J=7.6 Hz, 1H), 7.90 (d, J=2.8 Hz, 1H), 8.38-8.39 (m, 1H), 8.66-8.68 (m, 1H), 8.88 (s, 1H), 8.96 (d, J=1.6 Hz, 1H).

Provenance & Evidence