2-Pyrazinecarboxylic acid → 1,6-Dihydro-6-oxo-1-[2-(2-pyrazinylcarbonylamino)ethyl]-3-pyridinecarboxylic acid methyl ester

HRID 2379086Notes

Reaction equation

HRID 2379086 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH2:14])[CH:6]=1)=[O:4].[N:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21](O)=[O:22].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH:14][C:21]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][N:15]=2)=[O:22])[CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 539914951,6-Dihydro-6-oxo-1-[2-(2-pyrazinylcarbonylamino)ethyl]-3-pyridinecarboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.396 g, 2.02 mmol) was coupled with 2-pyrazinecarboxylic acid (0.251 g, 2.02 mmol) in a mixture of dichloromethane (34 ml) and dimethylformamide (35 ml) with triethylamine (1.41 ml, 10.1 mmol)and propylphosphonic acid anhydride (0.7 ml, added as a 0.7 ml ethyl acetate solution). After 18 hours, the mixture was concentrated and the residue slurried in dichloromethane and aqueous sodium bicarbonate. The layers were separated and the aqueous layer extracted with dichloromethane (2X) and the combined organic layers dried (Na2SO4). Filtration, concentration, and purification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane) gave the desired product, MP: 195°-197° C.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (2X)
  4. dry with materialthe combined organic layers dried (Na2SO4)
  5. filtrationFiltration, concentration, and purification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-811c07d4f77649279aa6a96f39177b3e
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

Loading…