Morpholine → HCID 57558055, Verbindung

HRID 1162925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162925
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:14]=[C:15]1[CH:19]([CH2:20]OS(C)(=O)=O)[CH2:18][CH2:17][N:16]1[C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[C:31]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]([F:46])([F:45])[F:44])[NH:32][C:33]2=[O:36])=[CH:28][CH:27]=1.[Cl-].[NH4+]>C1COCC1>[N:1]1([CH2:20][CH:19]2[CH2:18][CH2:17][N:16]([C:26]3[CH:35]=[C:34]4[C:29]([CH:30]=[C:31]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[C:43]([F:46])([F:45])[F:44])[NH:32][C:33]4=[O:36])=[CH:28][CH:27]=3)[C:15]2=[O:14])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 86626744Methanesulfonic acid 2-oxo-1-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]-pyrrolidin-3-ylmethyl ester

Produkt 1

HCID 57558055HCID 57558055, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Morpholine (0.024 ml, 0.29 mmol) and triethylamine (0.040 ml, 0.29 mmol) were added to a THF solution (1 ml) that contained the obtained methanesulfonic acid 2-oxo-1-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]-pyrrolidin-3-ylmethyl ester (14 mg, 0.029 mmol). The obtained mixture was heated to reflux for 16 hours. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1->30:1), so as to obtain 7-(3-morpholin-4-ylmethyl-2-oxo-pyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (3 mg, 22%) in the form of a colorless oil substance.

Aufarbeitung

  1. temperatureThe obtained mixture was heated
  2. temperatureto reflux for 16 hours
  3. extractionthe obtained mixture was then extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1->30:1)

Quellen und Nachweise

ORD-Eintrag
ord-246c720381834b9697144df8219efa39
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820693B2

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