1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529590, compound

HRID 1972714Notes

Reaction equation

HRID 1972714 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11](=[O:14])[CH2:12][Cl:13])[N:6]2[N:5]=[CH:4][N:3]=1.[Br:15]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:15])[CH:9]=[C:10]([C:11](=[O:14])[CH2:12][Cl:13])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 585293111-{4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-2-chloroethan-1-one

Product 1

HCID 58529590HCID 58529590, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-chloroethanone (500 mg, 2.37 mmol) in DMF (40 mL) at −40° C., was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (339 mg, 1.19 mmol). The reaction was allowed to stir for 1 hr while warming to rt. A precipitate had formed and the reaction was filtered and the precipitate was washed With Et2O to afford 360 mg (52%) of the desired product as a white powder. 1H NMR (300 MHz, DMSO-d6) 8.12 (s, 1 H), 7.53 (s, 1 H), 5.10 (s, 2H); LC-MS (m+H]+=291, RT=2.51 min.

Workup

  1. customA precipitate had formed
  2. filtrationthe reaction was filtered
  3. washthe precipitate was washed With Et2O

Sources & evidence

ORD record
ord-ba4adc6c1bca47b480a4a93885dcaa7a
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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