Triethylamine → N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide

HRID 626201Notes

Reaction equation

HRID 626201 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][NH:3]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:33][O:34][NH:35][CH3:36].CCN(CC)CC>C(Cl)Cl>[CH3:33][O:34][N:35]([CH3:36])[C:8]([C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=1)=[O:10]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2807562-Hydroxyisonicotinic Acid

Product 1

HCID 89655466N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-oxo-1,2-dihydropyridine-4-carboxylic acid (8.0 g, 1.0 eq), EDCI (13.2 g, 1.2 eq) and HOBt (9.3 g, 1.2 eq) in 150 mL CH2Cl2 were added N-methoxymethanamine hydrochloride (6.8 g, 1.2 eq) and Et3N (26.2 g, 4.5 eq). The reaction mixture was stirred at rt overnight, concentrated, and purified by column chromatography to give the desired product (6.3, 60% yield). 1H NMR (400 MHz, CDCl3) δ 12.79 (s, 1H), 7.40 (d, J=6.8 Hz, 1H), 6.77 (s, 1H), 6.43 (dd, J=6.8 Hz, 1.6 Hz, 1H), 3.62 (s, 3H), 3.34 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-cbd070787a61443098960d8247421e50
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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