StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethylamine → 7-(4-Dimethylcarbamoyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

HRID 1876289
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1876289
F[B-](F)(F)F.N1(O[C:16](N(C)C)=[N+:17](C)[CH3:18])C2C=CC=CC=2N=N1.[CH2:23]([O:30][C:31]([N:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([O:43][C:44]3[CH:49]=[CH:48][C:47]([C:50]([OH:52])=O)=[CH:46][CH:45]=3)=[CH:38][CH:39]=2)[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CNC.CN1CCOCC1>O1CCCC1>[CH2:23]([O:30][C:31]([N:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([O:43][C:44]3[CH:49]=[CH:48][C:47]([C:50](=[O:52])[N:17]([CH3:18])[CH3:16])=[CH:46][CH:45]=3)=[CH:38][CH:39]=2)[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584938387-(4-Carboxy-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Produkt 1

HCID 584939027-(4-Dimethylcarbamoyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.44 g) is added to a solution of 7-(4-carboxy-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester, dimethylamine (2 mol/L in tetrahydrofuran, 0.68 mL), and N-methyl-morpholine (0.41 mL) in tetrahydrofuran (20 mL) chilled in an ice bath. The cooling bath is removed and the resulting mixture is stirred at room temperature for 3 h. Then another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.70 mL) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.20 g) are added and the mixture is further stirred for another 4 h. After adding another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.30 mL), the mixture ist stirred at room temperature overnight. The mixture is concentrated and the residue is purified by chromatography on silica gel (ethyl acetate) to furnish the title compound.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionThen another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.70 mL) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.20 g) are added
  4. stirringthe mixture is further stirred for another 4 h
  5. additionAfter adding another portion of dimethylamine (2 mol/L in tetrahydrofuran, 0.30 mL)
  6. stirringthe mixture ist stirred at room temperature overnight
  7. concentrationThe mixture is concentrated
  8. customthe residue is purified by chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-734a6b6071454d9790d848dd4887acc3
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309597B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion