Bromine → HCID 22273571, compound

Reaction equation

[Br:1]Br.[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[CH:5]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:14]1[C:9]([C:8]2[N:4]([CH3:3])[CH:5]=[N:6][CH:7]=2)=[N:10][C:11]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:20][CH:21]=2)=[N:12][CH:13]=1

Participants

Procedure

Bromine (75.5 mg, 0.47 mmol) was added to a solution of 4-(1-methylimidazol-5-yl)-2-(4-sulphamoylanilino)pyrimidine (Example 15; 0.14 g, 0.42 mmol) and sodium acetate (41.7 mg, 0.51 mmol) in acetic acid (4 ml) and the mixture stirred for 1 hour. The volatiles were evaporated and the residue partitioned between EtOAc and saturated aqueous potassium hydrogen carbonate solution. The organic phase was separated and dried. The residue was pre-absorbed on to silica gel and purified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (9:1) to give the title compound (91 mg, 52%). NMR 10.14 (s, 1H), 8.75 (s, 1H), 7.90-7.69 (m, 4H), 7.17 (s, 2H), 3.84 (s, 3H); m/z 409.