Sodium Hydroxide → 7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-quinoxalin-2-yl-hept-1-en-3-one

HRID 860081

Reaktionsgleichung

Reaktionsgleichung von HRID 860081
COP([CH2:7][C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=1)(=O)OC.[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=[CH:32][C:31]=1[CH:40]=O.[OH-].[Na+]>C1COCC1>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:15]2[N:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:29])[CH:7]=[CH:40][C:31]3[CH:32]=[N:33][C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:30]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 594088Quinoxaline-2-carbaldehydeHCID 58765549{6-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-2-oxo-hexyl}-phosphonic acid dimethyl ester

Produkt 1

HCID 696661987-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-quinoxalin-2-yl-hept-1-en-3-oneAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-7 (12.0 g, 28.5 mmol) and quinoxaline-2-carbaldehyde 22-1 (4.51 g, 28.5 mmol) in THF (250 mL) at 0° C. was added 4M NaOH (7.49 mL, 29.9 mmol) dropwise. After 15 minutes the ice bath was removed and the mixture stirred for an additional 10 minutes. The solution was diluted with water, extracted with ethyl acetate, and dried (Na2SO4). Following concentration, the residue was triturated with ether to give 11.4 g (88%) of 22-2 as a white solid.

Aufarbeitung

  1. customAfter 15 minutes the ice bath was removed
  2. additionThe solution was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentration
  6. customthe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-e9eba28f4a4644f98c2b5e5cf2d910a1
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153862B2

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