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Morpholine → 2-[2-({3-[4-(morpholine-4-carbonyl)phenoxy]propyl}-pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

HRID 1504184
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1504184
Br[C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12][N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:4][CH:3]=1.[C:33](=[O:36])([O-])[O-].[Na+].[Na+].[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.C(OC(=O)C)C.[ClH:51]>C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].C(OCC)(=O)C.O.C1COCC1>[ClH:51].[ClH:51].[N:39]1([C:33]([C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH2:11][CH2:12][N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])=[CH:31][CH:32]=2)=[O:36])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 669599672-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one

Produkt 1

HCID 669600602-[2-({3-[4-(morpholine-4-carbonyl)phenoxy]propyl}-pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)KatalysatorHCID 178521658HCID 178521658, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

2-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one(500 mg), hexacarbonyl molybdenum(264 mg), trans-di-μ-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium (II) (Herrmann's palladacycle) (23 mg), sodium carbonate(318 mg), and morpholine(0.26 ml) were added to THF(5 ml). The mixture was heated at 170° C. for 10 minutes (microwave reactor). The reaction mixture was cooled to room temperature. Water and ethyl acetate were added thereto, followed by celite filtration. The organic layer was dried with sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate: methanol=1:0→7:3). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution was added to an ethyl acetate solution of the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound(150 mg) as a white powder.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfollowed by celite filtration
  3. dry with materialThe organic layer was dried with sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate: methanol=1:0→7:3)
  5. customcondensed under reduced pressure
  6. customThe precipitated insoluble matter was separated
  7. washwashed with ethyl acetate
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0b6ef63afbe44ef496d989adef40d42d
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09212187B2

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