N-bromobutanimide → HCID 67071846, compound

HRID 2094207Notes

Reaction equation

HRID 2094207 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]([NH:12][C:13]1[NH:14][C:15]2[C:20]([C:21]=1[C:22]([NH2:24])=[O:23])=[CH:19][CH:18]=[C:17]([O:25][CH3:26])[CH:16]=2)=[O:11]>CN(C)C=O.O>[NH2:9][C:10]([NH:12][C:13]1[NH:14][C:15]2[C:20]([C:21]=1[C:22]([NH2:24])=[O:23])=[CH:19][C:18]([Br:1])=[C:17]([O:25][CH3:26])[CH:16]=2)=[O:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 44609420HCID 44609420, compound

Product 1

HCID 67071846HCID 67071846, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under ice-cooling, a solution of N-bromosuccinimide (94 mg, 0.53 mmol) in anhydrous N,N-dimethylformamide (1 mL) was added to a solution of 2-aminocarbonylamino-6-methoxyindole-3-carboxamide (Compound No.1-1, 126 mg, 0.51 mmol) in anhydrous N,N-dimethylformamide (1.5 mL) and the mixture was stirred for 1.5 hours. Moreover the whole was stirred for 2 hours at room temperature and stirred for 3 hours at 50° C. After the reaction solution was diluted with water (60 mL) and extracted with ethyl acetate (50 mL), the organic layer was washed with brine (50 mL) and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, the obtained solid was filtered off and washed with a mixed solvent of diethyl ether-chloroform solution (5:1, 24 mL). The solid was dried at 40° C. under reduced pressure to give the title compound (50 mg) as a gray solid (30%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringMoreover the whole was stirred for 2 hours at room temperature
  3. stirringstirred for 3 hours at 50° C
  4. extractionextracted with ethyl acetate (50 mL)
  5. washthe organic layer was washed with brine (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter the solvent was removed under reduced pressure
  8. filtrationthe obtained solid was filtered off
  9. washwashed with a mixed solvent of diethyl ether-chloroform solution (5:1, 24 mL)
  10. customThe solid was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-9c061b00d2da437a91313310852b712a
Source dataset
uspto-grants-2013_05
Patent number
US08445529B2

Reaction notes

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