Cyanogen Bromide → HCID 10343270, compound

Participants

Reaction Steps

4-(3-Chloro-2-fluoroanilino)-7-methoxy-6-[(piperidin-4-yl)methoxy]quinazoline (Example 3, 104 mg, 0.25 mmol) was dissolved in DCM (10 ml), and diisopropylethylamine (4 μl, 0.28 mmol) was added. Cyanogen bromide solution (3M in DCM, 92 μl, 0.28 mmol) was added, and the solution stirred for 16 hours at ambient temperature. The solvent was evaporated, and the residue purified by chromatography, eluting with 0 to 2% (7:1 MeOH/concentrated aqueous NH4OH) in DCM. The appropriate fractions were combined and evaporated, and the residue triturated with diethyl ether to give the product as a white solid (75 mg, 68%); 1H NMR: 1.34-1.50 (m, 2H), 1.80-1.90 (m, 2H), 2.02 (m, 1H), 3.10 (m, 2H), 3.37-3.46 (m, 2H), 3.93 (s, 3H), 3.99 (d, 2H), 7.19 (s, 1H), 7.26 (dd, 1H), 7.46 (dd, 1H), 7.46 (dd, 1H), 7.50 (dd, 1H), 7.77 (s, 1H), 8.36 (s, 1H), 9.57 (s, 1H); Mass Spectrum: 442.4, 444.4.

Provenance & Evidence