N-bromobutanimide → HCID 178473908, compound
Reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[Br:26]N1C(=O)CCC1=O>CN(C)C=O>[Br:26][C:10]1[N:9]=[C:8]([C@H:11]2[CH2:12][CH2:13][C@H:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:25])[CH3:24])[CH2:21][CH2:22]3)[CH2:15][CH2:16]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-(4-((trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)piperazin-1-yl)ethanone (0.422 mmol, 144 mg) in N,N-dimethylformamide (2 mL) was added N-bromosuccinimide (0.422 mmol, 75 mg). After two hours at 60° C. the reaction was quenched with a saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The organic extracts were washed twice with water and brine, dried (sodium sulfate) and concentrated under reduced pressure. The crude product was purified with column chromatography on silica gel (dichloromethane/methanol) to afford 176 mg of the title compound.