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

HRID 2379084노트

반응식

HRID 2379084 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3008e11dfab04710b74644317a63ab06
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05360808

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