1,1'-Carbonyldiimidazole → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(3-oxo-isoxazolidin-5-ylmethyl)-nicotinamide

HRID 83129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83129
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:36][CH2:37][CH:38]1[O:42][NH:41][C:40](=[O:43])[CH2:39]1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:36][CH2:37][CH:38]2[O:42][NH:41][C:40](=[O:43])[CH2:39]2)=[O:21])=[CH:17][N:16]=1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 194439DihydromuscimolHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Produkt 1

HCID 775011846-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(3-oxo-isoxazolidin-5-ylmethyl)-nicotinamideAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.64 mmol) in DMF (2 mL) was added 1,1′-carbonyl-diimidazole (115 mg, 0.71 mmol) and the reaction mixture was stirred for 0.5 h at 80° C. After cooling to ambient temperature 5-aminomethyl-isoxazolidin-3-one (82 mg, 0.71 mmol) was added and stirring was continued for 1 h at this temperature and for 2 h at 80° C. It was diluted with ethyl acetate (10 mL) and washed with water (10 mL) and aqueous sodium chloride (saturated, 10 mL). The organic layer was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate:methanol=40:60:0 to 0:90:10) afforded the title compound (13 mg, 5%) as a white solid. MS: m/e=409.3 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 1 h at this temperature and for 2 h at 80° C
  4. washwashed with water (10 mL) and aqueous sodium chloride (saturated, 10 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, heptane:ethyl acetate:methanol=40:60:0 to 0:90:10)

Quellen und Nachweise

ORD-Eintrag
ord-25619d5b83ed493e8b2de532e3d1226b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846719B2

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