Diisopropylethylamine → 2-Chloro-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

HRID 1734122Notes

Reaction equation

HRID 1734122 reaction equation
[NH2:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].C(N(CC)C(C)C)(C)C>CCOC(C)=O>[Cl:11][C:12]1[C:13]([C:14]([NH:1][C:2]2[C:3]([O:9][CH3:10])=[N:4][CH:5]=[CH:6][C:7]=2[CH3:8])=[O:15])=[CH:17][CH:18]=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 103293612-Methoxy-4-methylpyridin-3-amine

Product 1

HCID 104236502-Chloro-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.4 g (2.9 mmol) of 3-amino-2-methoxy-4-methylpyridine and 0.5 g (2.9 mmol) of 2-chloronicotinoyl chloride in EtOAc at 0° C. was added 0.4 g (3.0 mmol) of N,N-diisopropylethylamine. Stirring was continued for 10 h at which point the mixture was washed with 0.1N HCl , dried (MgSO4), concentrated and purified by flash chromatography on silica gel (1:1 EtOAc:hexanes) to yield 0.7 g (88%) of the desired material. m.p.: 145°-146° C. (Recrystallized from ethyl acetate).

Workup

  1. washthe mixture was washed with 0.1N HCl
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography on silica gel (1:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-8230835e372b497d99e241341f267a11
Source dataset
uspto-grants-1996_07
Patent number
US05532358

Reaction notes

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