Isopropyl iodide → HCID 86720968, compound

HRID 524914Notes

Reaction equation

HRID 524914 reaction equation
[H-].[Na+].I[CH:4]([CH3:6])[CH3:5].[N+:7]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][N:19]2[CH2:22][CH2:23][NH:24][C:25](=[O:26])[CH:18]2[CH2:17]1)([O-:9])=[O:8]>C1COCC1>[CH:4]([N:24]1[CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][N:16]([C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N+:7]([O-:9])=[O:8])[CH2:17][CH:18]2[C:25]1=[O:26])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 86720969HCID 86720969, compound

Product 1

HCID 86720968HCID 86720968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (15.87 mg, 0.3967 mmol) then 2-iodopropane (73.56 mg, 43.19 μL, 0.4327 mmol) were added to a solution of 2-(3-nitro-4-pyridyl)-3,4,6,7,8,9a-hexahydro-1H-pyrazino[1,2-a]pyrazin-9-one (100 mg, 0.3606 mmol) (prepared according to a procedure similar to Step 1 of Preparation N-1) in THF (5 mL) under N2. The reaction mixture was stirred at reflux for 24 h then it was partitioned between EtOAc and a saturated bicarbonate aqueous solution. Combined organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo to produce an oil that was used in next step without further purification. MS (ES+) 320.1.

Workup

  1. customprepared
  2. temperatureat reflux for 24 h
  3. customit was partitioned between EtOAc
  4. extractionCombined organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto produce an oil that
  9. customwas used in next step without further purification

Sources & evidence

ORD record
ord-6a626b886eb840c9b72ca39490f15912
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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