1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → HCID 39468342, compound

HRID 1790217Notes

Reaction equation

HRID 1790217 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([O-:13])=O)=[N:9][CH:10]=1)=[O:4].[K+].S(Cl)(Cl)=O.[CH:19]([N:22]([CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:24][NH2:25])([CH3:21])[CH3:20].C(N(CC)CC)C>ClC(Cl)C.C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:13])[NH:25][CH2:24][CH2:23][N:22]([CH:26]([CH3:28])[CH3:27])[CH:19]([CH3:21])[CH3:20])=[N:9][CH:10]=1

Participants

8

Reactant 4

HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 23689970HCID 23689970, compound

Product 1

HCID 39468342HCID 39468342, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×HCID 63651,1-DichloroethaneSolvent

Procedure

A suspension of 1.1 g (5 mmol) potassium 5-methoxycarbonyl-pyridine-2-carboxylate, 0.9 ml (12 mmol) thionyl chloride and 0.1 ml DMF in 5 ml dichloroethane was heated at reflux for 2 h. To the reaction mixture 5 ml CH2Cl2 were added and the solvent was evaporated. This procedure was repeated three times. The residue was suspended in 5 ml CH2Cl2 and a solution of 9.95 ml (5.5 mmol) 2-diisopropylaminoethylamine, 0.97 ml (7 mmol) triethylamine, 0.1 ml DMF in 5 ml CH2Cl2 was added under ice-cooling. After stirring for 12 h at rt the organic phase was extracted with water, 5% citric acid and aqueous NaHCO3 and dried over magnesium sulfate. After evaporation of the solvent the residue was subjected to silica gel chromatography (20% MeOH and 1% triethylamine in ethyl acetate) to yield 1.15 g (3.7 mmol) 6-(2-diisopropylamino-ethylcarbamoyl)-nicotinic acid methyl ester; exact MW [M+H] calcd: 308.20; MW .found [M+H]: 308.20.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customthe solvent was evaporated
  4. temperaturecooling
  5. extractionwas extracted with water, 5% citric acid and aqueous NaHCO3
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvent the residue

Sources & evidence

ORD record
ord-d54340666b7148d9a6bdec48400dbcf4
Source dataset
uspto-grants-2006_07
Patent number
US07071219B2

Reaction notes

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