1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232239, compound

HRID 1099290Notes

Reaction equation

HRID 1099290 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[N:17]3[C:12]([C:13]([NH2:18])=[N:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:19]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[Br:19][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:17]2[C:12]=1[C:13]([NH2:18])=[N:14][CH:15]=[N:16]2

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 59231977HCID 59231977, compound

Product 1

HCID 59232239HCID 59232239, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-morpholin-4-ylethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (149 mg, 0.6 mmol) in DMF (3 ml) at −20 C was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (69 mg, 0.24 mmol) in three portions. The reaction was stirred at −20 C for 3 h. Upon the completion, the reaction was quenched with aqueous saturated Na2SO3 and allowed to warm up to rt. The crude was extracted with ethyl acetate. The organic layer was collected and washed with brine, dried over Na2SO4 and concentrated. The resulting crude was purified via column chromatography (95:5 v/v CH2Cl2—CH3OH) to afford 75 mg of the title compound as yellow solid (yield 39%). MS [M+H]+=326.2; LCMS RT=1.15 min.

Workup

  1. customUpon the completion, the reaction was quenched with aqueous saturated Na2SO3
  2. extractionThe crude was extracted with ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting crude was purified via column chromatography (95:5 v/v CH2Cl2—CH3OH)

Sources & evidence

ORD record
ord-324739bb049a4afcbad31f5ded105d11
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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