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

HRID 2379084ノート

反応式

HRID 2379084 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].[CH3:15][C:16]1[N:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl.C(OCC)(=O)C>[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:22]([C:19]2[CH:20]=[N:21][C:16]([CH3:15])=[CH:17][CH:18]=2)=[O:23])[CH:6]=1)=[O:4]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 1378606-Methylnicotinic acidHCID 516892Sodium BicarbonateHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

生成物 1

HCID 540152651,6-Dihydro-1-[2-(6-methyl-3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.50 g, 2.55 mmol) was coupled with 6-methyl-3-pyridinecarboxylic acid (0.42 g, 3.1 mmol)in dimethylformamide (42.5 ml) with triethylamine (1.80 ml, 12.75 mmol) and propylphosphonic acid anhydride (0.90 ml, added as a 0.90 ml ethyl acetate solution). After 72 hours, dichloromethane and aqueous sodium bicarbonate were added. The layers were separated and the organic layer washed with brine and dried (Na2SO4). Filtration, concentration, and purification by medium pressure liquid chromotography (silica gel, 4-6% methanol/dichloromethane) gave the desired product, MP: 184°-185° C.

後処理

  1. customThe layers were separated
  2. washthe organic layer washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationFiltration, concentration, and purification by medium pressure liquid chromotography (silica gel, 4-6% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-3008e11dfab04710b74644317a63ab06
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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