1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529901, compound

HRID 1972885Notes

Reaction equation

HRID 1972885 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([C:15]2[N:23]3[C:18]([C:19]([NH2:24])=[N:20][CH:21]=[N:22]3)=[CH:17][CH:16]=2)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:25]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([C:15]2[N:23]3[C:18]([C:19]([NH2:24])=[N:20][CH:21]=[N:22]3)=[C:17]([Br:25])[CH:16]=2)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 58529945HCID 58529945, compound

Product 1

HCID 58529901HCID 58529901, compoundYield 164.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a cooled (−20° C.) solution of 3-(4-amino-pyrrolo[2,1-f][1,2,4]triazine-7-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.19 g, 3.59 mmol) in tetrahydrofuran (35 mL) was added THF solution of 1,3-dibromo-5,5-dimethylhydantoin (0.56 g, 1.97 mmol). The mixture was allowed to stir (−20° C.) for 2 h and then allowed to warm to rt. The reaction was quenched with the addition of 10% aqueous Na2S2O3 solution. The mixture was extracted with ethyl acetate (3×75 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness. The crude material was purified by Biotage® chromatography using a gradient of 50% to 75% ethyl acetate in hexanes to afford 1.33 g (90%) of the desired product. 1H NMR (300 MHz, CD3OD-d4) δ 8.00 (s, 1 H), 7.45 (d, 1 H), 6.94 (d, 1 H), 4.44-4.32 (m, 1 H), 3.65-3.59 (m, 2 H), 3.47-3.38 (m, 2 H), 2.31-2.11 (m, 2 H), 1.45 (s, 9 H); LC-MS [M+H]+=411.7, RT=2.98 min.

Workup

  1. temperatureto warm to rt
  2. customThe reaction was quenched with the addition of 10% aqueous Na2S2O3 solution
  3. extractionThe mixture was extracted with ethyl acetate (3×75 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by Biotage® chromatography

Sources & evidence

ORD record
ord-2e02bcaf38c7430eb838bc8c500896b2
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…