Dimethylformamide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

HRID 1245739Notes

Reaction equation

HRID 1245739 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1Cl.[CH3:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1N(C)C.[C:29](=O)([O-])[O-].[K+].[K+].C[N:36]([CH:38]=O)C>[Cu]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[NH:36][C:38]1[C:25]([CH3:21])=[CH:26][C:27]([CH3:29])=[CH:28][C:20]=1[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11869N,N,2-TrimethylanilineHCID 248068762-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 695872624-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester, trimethylaniline, potassium carbonate, copper in DMF was heated at reflux. The mixture was quenched with ammonium chloride and stirred for 20 min, filtered through celite and washed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give the title compound as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe mixture was quenched with ammonium chloride
  4. filtrationfiltered through celite
  5. washwashed with ethyl acetate
  6. extractionThe filtrate was extracted with ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-4f03e17beaa84580b5c35b5b6b64d128
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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