Water → HCID 10180885, compound

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:5][NH:6][C:7]([C:9]1[C:18]([OH:19])=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][N:10]=1)=[O:8].[Br:24]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:24][C:11]1[N:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]2[CH:20]=[C:21]([Cl:23])[CH:22]=[C:2]([Cl:1])[CH:3]=2)=[O:8])[C:18]([OH:19])=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2

Participants

Procedure

To a solution of N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 1, Step 3 (1.28 g, 3.69 mmol) in CH2Cl2 (100 ml) at room temperature was added N-bromosuccinimide (0.689 g, 3.87 mmol). The reaction was stirred for 4 hrs and then poured into water. The organic phase was washed with water (3×100 ml), and dried (Na2SO4). The solvent was evaporated in vacuo and the residue triturated with CH2Cl2 to afford the title compound as an off white solid.