N-Iodosuccinimide → HCID 71237842, compound

HRID 340077Notes

Reaction equation

HRID 340077 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[N:15]=[CH:16][NH:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([I:25])C(=O)C1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2[N:17]=[C:16]([I:25])[NH:15][C:12]=2[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 71238308HCID 71238308, compound

Product 1

HCID 71237842HCID 71237842, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carboxylic acid tert-butyl ester (Preparation 27, 4.8 g, 20.23 mmol) in THF (60 mL) was added NIS (4.78 g, 21.24 mmol). The reaction was stirred at room temperature for 18 hours and the solvent was then removed in vacuo. The residue was dissolved in EtOAc (200 mL) and the resulting solution was washed with sodium thiosulfate solution (150 mL). The aqueous layer was re-extracted with EtOAc (150 mL) and the combined organic layers were washed with brine (150 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (6.14 g) in an 84% yield.

Workup

  1. customthe solvent was then removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. washthe resulting solution was washed with sodium thiosulfate solution (150 mL)
  4. extractionThe aqueous layer was re-extracted with EtOAc (150 mL)
  5. washthe combined organic layers were washed with brine (150 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90f183b6c6464ec1bdb15a488a8c8308
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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