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

HRID 2379086ノート

反応式

HRID 2379086 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-811c07d4f77649279aa6a96f39177b3e
出典データセット
uspto-grants-1994_11
特許番号
US05360808

反応ノート

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