4-Chlorobenzylamine → HCID 9805202, compound

Participants

Reaction Steps

A solution of bromoacetic anhydride (1.03 g, 4 mmol) in THF (3.0 mL) is added over 30 min to a stirred solution of N-(4-chlorobenzyl)-4-hydroxy-8-(methylamino)-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (308 mg of a 1:1 mixture of compound 9 and 4-chlorobenzylamine), triethylamine (500 mg, 5 mmol) in THF (7.0 mL). After 5 h, methanol (20 mL) and triethylamine (300 mg) are added, and the solution is stirred at room temperature overnight. The solution is evaporated, dissolved in chloroform/methanol, and is applied in chloroform to a silica gel column which is eluted with chloroform and then with 5-10% methanol/chloroform to give the title compound (98 mg) which is precipitated from acetonitrile.

Provenance & Evidence