Diisopropylamine → 2-ethoxy-N,N-di(propan-2-yl)pyridine-4-carboxamide

HRID 1802449Notes

Reaction equation

HRID 1802449 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][N:12]=1)[C:7]([OH:9])=O)[CH3:2].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH:26]([NH:29][CH:30]([CH3:32])[CH3:31])([CH3:28])[CH3:27].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][N:12]=1)[C:7]([N:29]([CH:30]([CH3:32])[CH3:31])[CH:26]([CH3:28])[CH3:27])=[O:9])[CH3:2]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 5924012-Ethoxyisonicotinic acid

Product 1

HCID 594360062-ethoxy-N,N-di(propan-2-yl)pyridine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-ethoxyisonicotinic acid (20 g, 120 mmol) in CH2Cl2 (500 mL) was added oxalyl chloride (10.4 mL) followed by one drop of DMF. The solution was stirred for 2 hr then triethylamine (33.4 mL, 239 mmol) and diisopropyl amine (25 mL, 179 mmol) were added dropwise. The solution was allowed to stir for 12 hr then worked up with CH2Cl2 and sat. NaHCO3. The crude mixture was purified by silica gel chromatography (100% hexanes to 100% EtOAc) to afford the title compound.

Workup

  1. stirringto stir for 12 hr
  2. customThe crude mixture was purified by silica gel chromatography (100% hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-9d3380fefed7437885e5c5ed9782ea6d
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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