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

HRID 626187Notes

Reaction equation

HRID 626187 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][C:3]1=[O:11].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:34][O:35][NH:36][CH3:37].CCN(CC)CC>C(Cl)Cl.O>[CH3:34][O:35][N:36]([CH3:37])[C:8]([C:5]1[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:11])[CH:4]=1)=[O:10]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 8199231-Methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 60731291N-methoxy-N,1-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (540 mg, 1.0 eq), EDCI (811 mg, 1.2 eq) and HOBt (572 mg, 1.2 eq) in 20 mL CH2Cl2 was stirred at r.t. for 5 min Then N-methoxymethanamine hydrochloride (413 mg, 1.2 eq) and Et3N (1.1 g, 3.0 eq) were added, and the reaction was stirred at rt overnight. 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 (555 mg, 80% yield). 1H NMR (400 MHz, CDCl3) δ 7.32 (d, J=6.8 Hz, 1H), 6.78 (s, 1H), 6.32 (dd, J=6.8 Hz, 1.6 Hz, 1H), 3.61 (s, 3H), 3.57 (s, 3H), 3.32 (s, 3H).

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. extractionthe mixture was extracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-7c8c0342604f423098d0b29ccd24be19
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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