Pyridine → 1-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-pheny-1H-indene-2-carboxylic acid cyclohexylamide

HRID 19557

Reaktionsgleichung

Reaktionsgleichung von HRID 19557
[CH:1]1([NH:7][C:8]([C:10]2[C:11](=O)[C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[C:14]([O:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:13]=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:36][OH:37].N1C=CC=CC=1>C(O)C>[CH:1]1([NH:7][C:8]([C:10]2[C:11](=[N:36][OH:37])[C:12]3[C:17]([C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][CH:15]=[C:14]([O:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:13]=3)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 686983496-(2-morpholine-4-ylethoxy)-1-oxo-3-pheny-1H-indene-2-carboxylic acid cyclohexylamide

Produkt 1

HCID 866153141-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-pheny-1H-indene-2-carboxylic acid cyclohexylamideAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6-(2-Morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (130 mg, 0.28%) obtained in Step 4 was dissolved in ethanol (20 mL), and hydroxylamine hydrochloride (60 mg, 0.85 mmol) and pyridine (892 mg, 1.13 mmol) were added thereto. The mixture was refluxed for 1 hr, and cooled to RT, and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 86 mg of 1-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (yield: 64%). Subsequently, 1-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (80 mg, 0.17 mmol) thus obtained was dissolved in methanol (20 mL) and 10%-palladium (100 mg) was added thereto. The mixture was stirred for 15 hrs at RT while providing H2 gas thereto using a balloon, filtered through celite, and concentrated under a reduced pressure. Then, the resulting residue was purified by flash chromatography to obtain 14 mg of the titled compound (yield: 18%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 hr
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fd7b1b84ee4b42b392ba7009b775e8b3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745439B2

Verknüpfte Notizen

Wird geladen…