1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529616, compound

HRID 1972739Notes

Reaction equation

HRID 1972739 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:25]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[NH2:1][C:2]1[C:7]2=[C:8]([Br:25])[CH:9]=[C:10]([CH:11]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 58529895HCID 58529895, compound

Product 1

HCID 58529616HCID 58529616, compoundYield 195.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a cooled (−20° C.) solution tert-butyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)azepane-1-carboxylate (1.44 g, 4.35 mmol) in tetrahydrofuran (22 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (621 mg, 2.17 mmol) in 4 portions over 15 min. The mixture was allowed to stir (−20° C.) for 4 h. The reaction was quenched with the addition 5% aqueous K2CO3 (20 mL) and was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with 5% aqueous K2CO3 (25 mL), brine, dried (Na2SO4) and evaporated to provide 1.74 g (98%) of the desired product, which contained trace impurities. ES-MS m/z 411.91 [M+H]+, HPLC RT (min) 2.92.

Workup

  1. customThe reaction was quenched with the addition 5% aqueous K2CO3 (20 mL)
  2. temperatureto warm to rt
  3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic layers were washed with 5% aqueous K2CO3 (25 mL), brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-1cc3dc65e5684819b33bc62ac9ff8e06
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…