Potassium Carbonate → HCID 67115180, compound

HRID 77371Notes

Reaction equation

HRID 77371 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[C:7]([NH:9][CH2:10][C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[N:29]12[CH2:37][CH2:36][CH:33]([CH2:34][CH2:35]1)[NH:32][CH2:31][CH2:30]2>C(#N)C>[N:29]12[CH2:37][CH2:36][CH:33]([CH2:34][CH2:35]1)[N:32]([C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[C:7]([NH:9][CH2:10][C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[O:8])[CH2:31][CH2:30]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173368391,4-Diazabicyclo[3.2.2]nonane dihydrochlorideHCID 44203076HCID 44203076, compound2×

Product 1

HCID 67115180HCID 67115180, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
96 °C

Procedure

To a solution of 5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (Intermediate 2A) (7.39 g, 26.1 mmol) in acetonitrile (240 mL) was added potassium carbonate (14.6 g, 104 mmol) followed by 1,4-diazabicyclo[3.2.2]nonane dihydrochloride (5.45 g, 27.4 mmol). The resulting suspension was heated to reflux at 96° C. overnight. The reaction mixture was filtered and concentrated. Sample was diluted in methanol (100 mL) and split between two 20 g SCX cartridges. Purification by SCX and evaporation to dryness afforded 5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (7.0 g, 18.0 mmol).

Workup

  1. temperatureThe resulting suspension was heated
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. additionSample was diluted in methanol (100 mL)
  5. customsplit between two 20 g SCX cartridges
  6. customPurification
  7. customby SCX and evaporation to dryness

Sources & evidence

ORD record
ord-ef3b12aa24f4418e97fd06fe1d326042
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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