Cyanogen Bromide → HCID 86585882, compound

HRID 2120404Notes

Reaction equation

HRID 2120404 reaction equation
[CH2:1]([CH:8]([NH:23][C:24]([C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1)=[O:25])[CH:9]([OH:22])[CH2:10][CH:11]([C:18]([NH:20][NH2:21])=[O:19])[CH2:12][CH2:13][C:14]([F:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:36]#[C:37]Br.C(=O)([O-])O.[K+]>O1CCOCC1.O>[NH2:36][C:37]1[O:19][C:18]([CH:11]([CH2:12][CH2:13][C:14]([F:17])([CH3:16])[CH3:15])[CH2:10][CH:9]([OH:22])[CH:8]([NH:23][C:24]([C:26]2[CH:35]=[N:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)=[O:25])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:20][N:21]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516893Potassium BicarbonateHCID 74990038HCID 74990038, compound

Product 1

HCID 86585882HCID 86585882, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of quinoxaline-2-carboxylic acid (1-benzyl-7-fluoro-4-hydrazinocarbonyl-2-hydroxy-7-methyl-octyl)-amide (110 mg, 0.228 mmol) in dioxane (0.5 mL) and water (0.5 mL) was added cyanogen bromide (31 mg, 0.296 mmol) and potassium hydrogencarbonate (31 mg, 0.310 mmol). The reaction was heated to reflux for 1 hour then cooled to ambient termperature. The dioxane/water was removed by adding benzene (5 mL) and concentrating (2×). The remaining solid was dissolved in ethyl acetate and water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated. Recrystallization of the crude product using a mixture of ethyl acetate, hexanes and methanol gave the title compound (64 mg, 55%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. temperaturethen cooled
  4. customThe dioxane/water was removed
  5. additionby adding benzene (5 mL)
  6. concentrationconcentrating (2×)
  7. dissolutionThe remaining solid was dissolved in ethyl acetate
  8. customThe layers were separated
  9. extractionthe aqueous layer extracted with ethyl acetate
  10. dry with materialThe combined organics were dried over sodium sulfate
  11. concentrationconcentrated
  12. customRecrystallization of the crude product
  13. additiona mixture of ethyl acetate, hexanes and methanol

Sources & evidence

ORD record
ord-57a12da044be4ecd9349e45215b5e93a
Source dataset
uspto-grants-2004_02
Patent number
US06689886B2

Reaction notes

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