N,N-Dimethylethylenediamine → 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide

HRID 1809617Notes

Reaction equation

HRID 1809617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38].CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:38][CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])=[O:10])[CH:3]=1

Participants

8

Reactant 5

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 430882584-chloro-N-(2-(dimethylamino)ethyl)picolinamideYield 108.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
33 °C

Procedure

4-Chloropicolinic acid (0.50 g, 3.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.67 g, 3.5 mmol) and 1-hydroxybenzotriazole hydrate (0.53 g, 3.5 mmol) were dissolved in DMF (6 mL). N1,N1-dimethylethane-1,2-diamine (0.381 mL, 3.49 mmol) and DIEA (0.62 mL, 3.5 mmol) were added, and the reaction was stirred at 33° C. overnight. The solution was cooled, diluted with water and extracted with methylene chloride. The organic layer was dried and concentrated to give the crude 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide (0.79 g).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with methylene chloride
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40fb5bdcbbc84ab48721f0cba0d8281c
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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