Dimethylamine → 1433965-43-5

HRID 2178106Notes

Reaction equation

HRID 2178106 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH2:11]([N:13](CC)[CH2:14]C)C.CNC.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:13]([CH3:14])[CH3:11])=[O:5]

Participants

9

Reactant 6

HCID 674DimethylamineHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2332622-Bromopyridine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 904493621433965-43-5Yield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In DMF (20 mL) was dissolved 2-bromonicotinic acid (2.00 g, 9.90 mmol). To this were added triethylamine (4.14 mL, 29.7 mmol), dimethylamine (2 mol/L solution in THF, 9.90 mL, 19.8 mmol), 1-hydroxybenzotriazole monohydrate (2.27 g, 14.85 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.85 g, 14.85 mmol), and the mixture was stirred at room temperature for 12 hours. A saturated aqueous ammonium chloride solution was added to the mixture and extraction with ethyl acetate was performed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated from the filtrate under-reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give compound DA1 (1.40 g, 60% yield).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated from the filtrate under-reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customto give compound DA1 (1.40 g, 60% yield)

Sources & evidence

ORD record
ord-c9e2a330ff274a81a862b5095b66dbb1
Source dataset
uspto-grants-2015_06
Patent number
US09067923B2

Reaction notes

Loading…