Potassium Carbonate → 5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamide

HRID 77383Notes

Reaction equation

HRID 77383 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.[N:29]12[CH2:37][CH2:36][CH:33]([CH2:34][CH2:35]1)[NH:32][CH2:31][CH2:30]2>C(#N)C.O>[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+:13]([O-:15])=[O:14])=[C:6]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:7]=1)[CH2:31][CH2:30]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 671149565-fluoro-N-methyl-2-nitrobenzene-1-sulfonamide2×HCID 681603131,4-Diazabicyclo[3.2.2]nonane 2,2,2-trifluoroacetate

Product 1

HCID 671149585-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamideYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
96 °C

Procedure

To a solution of 5-fluoro-N-methyl-2-nitrobenzenesulfonamide (Intermediate 16A) (1.0 g, 4.27 mmol) in acetonitrile (10 mL) was added potassium carbonate (1.77 g, 12.81 mmol) followed by 1,4-diazabicyclo[3.2.2]nonane 2,2,2-trifluoroacetate (1.17 g, 4.27 mmol). The resulting suspension was heated to reflux at 96° C. overnight. The reaction mixture was diluted in water (50 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-methyl-2-nitrobenzenesulfonamide (1.17 g, 3.44 mmol).

Workup

  1. temperatureThe resulting suspension was heated
  2. customsplit between two 20 g SCX cartridges
  3. customPurification
  4. customby SCX and evaporation to dryness

Sources & evidence

ORD record
ord-5da6d9d422e242b4a658ebd983378af4
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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