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

HRID 2379086노트

반응식

HRID 2379086 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].[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-811c07d4f77649279aa6a96f39177b3e
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05360808

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