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

HRID 2379083노트

반응식

HRID 2379083 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].[Cl:15][C:16]1[N:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1.ClCCl.C(N(CC)CC)C>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]([Cl:15])=[CH:17][CH:18]=2)=[O:23])[CH:6]=1)=[O:4]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

생성물 1

HCID 543131641,6-Dihydro-1-[2-(6-chloro-3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid methyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
-8 °C

실험 절차

To a 1 00 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet was added the above amine (0.300 g, 1.53 mmol), 6-chloro-3-pyridinecarboxylic acid (0.241 g, 1.53 mmol), and dry dichloromethane 125.5 mmol). Upon cooling in a -8° C. ice bath with stirring, triethyl amine (1.07 ml, 7.65 mmol) and propylphosphonic acid anhydride (0.50 ml, added as a 0.50 ml ethyl acetate solution, Angew. Chemie 1980, 92(2), 129) were added. The flask was allowed to warm slowly to room temperature over 1.25 hours. Stirring was continued 30 minutes at which time the reaction mixture solution was washed with aqueous sodium bicarbonate (2X), brine, and dried (Na2SO4). Filtration, concentration and purification via medium pressure liquid chromotography (silica gel, 4% methanol/dichloromethane) have the desired product, MP: 188°-190° C.

후처리

  1. customTo a 1 00 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet
  2. additionChemie 1980, 92(2), 129) were added
  3. temperatureto warm slowly to room temperature over 1.25 hours
  4. stirringStirring
  5. washthe reaction mixture solution was washed with aqueous sodium bicarbonate (2X), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration, concentration and purification via medium pressure liquid chromotography (silica gel, 4% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-97581b149c074b2ba518256dc6b2ef9d
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05360808

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