N-bromobutanimide → HCID 57600199, compound

HRID 1787828Notes

Reaction equation

HRID 1787828 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][CH2:15][C:16]3[N:20]4[C:21](=[O:33])[C:22]5[NH:23][CH:24]=[N:25][C:26]=5[N:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:19]4=[N:18][N:17]=3)[N:10]=2)=[CH:5][CH:4]=1.[Br:34]N1C(=O)CCC1=O>CN(C=O)C>[Br:34][C:24]1[NH:23][C:22]2[C:21](=[O:33])[N:20]3[C:16]([CH2:15][CH2:14][C:11]4[N:10]=[C:9]([C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)[O:13][N:12]=4)=[N:17][N:18]=[C:19]3[N:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:26]=2[N:25]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57600178HCID 57600178, compound

Product 1

HCID 57600199HCID 57600199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-2-[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]ethyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (160 mg, 0.36 mmol) in DMF (15 mL) at room temperature was added N-bromosuccinimide (110 mg, 0.61 mmol). After stirring at 70° C. for 1 hour, the reaction mixture was concentrated and purified by preparative LCMS to provide the desired product. LCMS calculated for C22H24BrN8O3 (M+H): 527.1, 529.0; found: 527.0, 529.0.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-6eb5ef580e5a4a8f893463dc31a9c088
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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