Triethylamine → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide

HRID 1501282Notes

Reaction equation

HRID 1501282 reaction equation
[CH3:1][C:2]1[C:3](=[O:20])[N:4]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH:5]=[C:6]([CH3:11])[C:7]=1[C:8]([OH:10])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:49][CH2:50][C:51]1[C:52](=[O:59])[NH:53][C:54]([CH3:58])=[CH:55][C:56]=1[CH3:57]>ClCCl>[CH3:57][C:56]1[CH:55]=[C:54]([CH3:58])[NH:53][C:52](=[O:59])[C:51]=1[CH2:50][NH:49][C:8]([C:7]1[C:6]([CH3:11])=[CH:5][N:4]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:3](=[O:20])[C:2]=1[CH3:1])=[O:10]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 895851503,5-Dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 89583011N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamideYield 7.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid (0.07 g, 0.26 mmol) in dichloromethane (10 mL) was added EDCI (0.06 g, 0.39 mmol), HOBt (0.05 g, 0.38 mmol) and triethylamine (0.078 g, 0.77 mmol). After stirred for 30 min, 3-(aminomethyl)-4,6-dimethyl pyridin-2(1H)-one (0.058 g, 0.39 mmol) was added and the reaction mixture was stirred at room temperature for 3 hours. The solution was concentrated under vacuum. The residue was diluted with water (20 mL) and extracted with ethyl acetate (20 mL). The extractions were combined, washed with H2O, dried over Na2SO4, and concentrated under vacuum. The residue was purified by prep. HPLC (Condition: Column: YMC C18 150*30 mm*5 um; Mobile phase A: water with 0.05% ammonia solution Mobile phase B: MeCN; column temperature: 30° C.; Gradient: A/B, 35-65%) to give N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide as yellow solid. (7.5 mg, yield 7.1%)

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3 hours
  2. concentrationThe solution was concentrated under vacuum
  3. additionThe residue was diluted with water (20 mL)
  4. extractionextracted with ethyl acetate (20 mL)
  5. extractionThe extractions
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by prep
  10. custom30° C.

Sources & evidence

ORD record
ord-1e3caa9f5e744d65807dfb55cb65eecc
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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