Benzylamine → 1-Ethyl-2-oxo-5,6-dimethyl-1,2-dihydropyridine-3-carboxylic acid benzylamide

HRID 416570Notes

Reaction equation

HRID 416570 reaction equation
[CH2:1]([N:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[CH:6]=[C:5]([C:11]([OH:13])=O)[C:4]1=[O:14])[CH3:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([NH:22][C:11]([C:5]1[C:4](=[O:14])[N:3]([CH2:1][CH3:2])[C:8]([CH3:9])=[C:7]([CH3:10])[CH:6]=1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 222665051-Ethyl-3-carboxy-5,6-dimethyl-2-pyridone

Product 1

HCID 235880331-Ethyl-2-oxo-5,6-dimethyl-1,2-dihydropyridine-3-carboxylic acid benzylamideYield 91.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-3-carboxy-5,6-dimethyl-2-pyridone (3-003-04) (195 mg) was dissolved in DMF (3 mL), and to the reaction mixture were added benzylamine (0.17 mL), diisopropylethylamine (0.35 mL), and benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 624 mg), and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate, washed twice with hydrochloric acid and aqueous sodium bicarbonate solution, respectively, and water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue (0.40 g) was subjected to silica gel (30 g) column chromatography (chloroform) to give 1-ethyl-2-oxo-5,6-dimethyl-1,2-dihydropyridine-3-carboxylic acid benzylamide (3-003) (259 mg, 91.1%) as a crystal, followed by recrystallization from methylene/n-hexane to give colorless needle crystal (207 mg, 72.9%, m.p. 117° C.) Examples 3-001 to 3-036 were synthesized in similar manner as Example 3-004.

Workup

  1. washwashed twice with hydrochloric acid and aqueous sodium bicarbonate solution
  2. dry with materialrespectively, and water, dried over magnesium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-16b25f8737b54bc49af755a4d0fb0ac9
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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