Dimethylamine → HCID 57900559, compound

HRID 1672357Notes

Reaction equation

HRID 1672357 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][NH:24][CH3:25]>C(#N)C>[CH3:23][N:24]([CH3:25])[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 43152698HCID 43152698, compound

Product 1

HCID 57900559HCID 57900559, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a room-temperature mixture containing 6-chloro-3-nitro-N-(pentan-3-yl)pyridin-2-amine (250 mg, 0.90 mmol) and potassium carbonate (250 mg, 1.8 mmol) in acetonitrile (2 mL) was added dimethylamine (1.35 mL, 1.0 M, 1.35 mmol) by syringe. After 3 h, the reaction mixture was concentrated in vacuo and then re-dissolved in EtOAc and water. The organic layer was washed twice with water and once with brine, dried over sodium sulfate, filtered and concentrated In vacuo. Silica gel chromatography (5%-20% EtOAc/Hexanes) provided the title compound as a yellow solid (119 mg, 52%). m/z=253.2 (M+H)+

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionre-dissolved in EtOAc
  3. washThe organic layer was washed twice with water and once with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated In vacuo

Sources & evidence

ORD record
ord-d8f48422a2044df9b38487762184d90c
Source dataset
uspto-grants-2011_08
Patent number
US07998976B2

Reaction notes

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