1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232208, compound

HRID 1099305Notes

Reaction equation

HRID 1099305 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]([NH:13][CH2:14][CH:15]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.[Br:28]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([Br:28])[CH:9]=[C:10]([C:11]([NH:13][CH2:14][CH:15]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 59232198HCID 59232198, compound

Product 1

HCID 59232208HCID 59232208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-({[(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)carbonyl]amino}methyl)morpholine-4-carboxylate (100 mg, 0.27 mmol) in THF (5 mL) was cooled to −50° C. and treated with 1,3-dibromo-5,5-dimethylhydantoin (37 mg, 0.13 mmol) in portions over 30 min. The reaction was then quenched with satd. Na2SO3 and warmed to rt. The product was extracted with EtOAc, dried (MgSO4), and concentrated. The crude product was triturated with EtOAc and filtered. A white solid was collected (60 mg, 50%). MS [M+H]+=545.96, 456.86; LCMS RT=2.90 min.

Workup

  1. customThe reaction was then quenched with satd
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was triturated with EtOAc
  6. filtrationfiltered
  7. customA white solid was collected (60 mg, 50%)

Sources & evidence

ORD record
ord-bd2f0e4029f448d2bcec98371fc3e031
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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