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

3-Methyl-4-pyridinamine → 2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amide

HRID 564728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 564728
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[N+](C1C=CC([O:28][C:29]([C:31]2[C:32]3[CH:41]=[C:40]([C:42]([O:46][CH3:47])([O:44][CH3:45])[CH3:43])[O:39][C:33]=3[C:34]([O:37][CH3:38])=[N:35][CH:36]=2)=O)=CC=1)([O-])=O>CN(C)C=O>[CH3:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:1][C:29]([C:31]1[C:32]2[CH:41]=[C:40]([C:42]([O:44][CH3:45])([O:46][CH3:47])[CH3:43])[O:39][C:33]=2[C:34]([O:37][CH3:38])=[N:35][CH:36]=1)=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 748113-Methyl-4-pyridinamineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 545256332-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Produkt 1

HCID 700816022-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amideAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A solution of 4-amino-3-methylpyridine (0.11 g) in dry N,N-dimethylformamide (20 ml) was stirred at 0° C. under an atmosphere of dry nitrogen. Sodium bis(trimethylsilyl)amide (1.0M solution in tetrahydrofuran, 1.0 ml) was added and stirring continued at 0° C. for 10 minutes. 2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.20 g) was added and stirring continued at room temperature for 90 minutes. The solvent was then removed in vacuo, the residue taken up in water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (100 ml), then brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with ethyl acetate gave the title compound (0.15 g) as a white solid.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at room temperature for 90 minutes
  3. customThe solvent was then removed in vacuo
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic extracts were washed with water (100 ml)
  6. dry with materialbrine (50 ml), dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customPurification by column chromatography on silica eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bceb532c9c9a447abcb1f89167b54ca4
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06169090A

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion