Water → 1-(3-(dimethylamino)propyl)-N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide

HRID 626202Notes

Reaction equation

HRID 626202 reaction equation
[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:12])[CH:7]=1)=[O:5].Cl.Cl[CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][CH2:16][N:9]1[CH:10]=[CH:11][C:6]([C:4]([N:3]([O:2][CH3:1])[CH3:13])=[O:5])=[CH:7][C:8]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 89655466N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide

Product 1

HCID 896728791-(3-(dimethylamino)propyl)-N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carbox-amide (200 mg, 1.0 eq), 3-chloro-N,N-dimethylpropan-1-amine hydrochloride (350 mg, 2.0 eq) and K2CO3 (455 mg, 3.0 eq) in 20 mL acetone was heated under reflux overnight. After cooling to rt, water was added, and the mixture was extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (255 mg, 87% yield). 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=7.2 Hz, 1H), 6.75 (d, J=1.2 Hz, 1H), 6.30 (dd, J=6.8 Hz, 2.0 Hz, 1H), 4.02 (t, J=7.2 Hz, 2H), 3.62 (s, 3H), 3.33 (s, 3H), 2.30 (t, J=6.8 Hz, 2H), 2.23 (s, 6H), 1.93 (t, J=7.2 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with CH2Cl2
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-73685238b6254e6a8df93eb43b99d1e5
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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