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Tetrahydrofuran → HCID 59255162, Verbindung

HRID 1694078
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1694078
O1CCCC1.[C:6]([C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[CH:12][CH:13]=1)#[CH:7].[F:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][C:28](Cl)=[N:29][OH:30])=[CH:23][CH:22]=1.C(N(CC)CC)C>O>[F:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][C:28]2[CH:7]=[C:6]([C:8]3[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[CH:12][CH:13]=3)[O:30][N:29]=2)=[CH:23][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262903(6-(3-Fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride

Produkt 1

HCID 59255162HCID 59255162, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a tetrahydrofuran (2 mL) solution of 3-ethynyl-pyridin-2,6-diamine (10 mg, 75 mmol) described in Manufacturing Example 13-1-3 and (6-(3-fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride (42 mg, 0.15 mmol) described in Manufacturing Example 71-1-4 was added triethylamine (21 μL, 0.15 mmol), which was stirred for 1 hour at 50° C. under nitrogen atmosphere. Water was added at room temperature to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=20:1) to obtain the title compound (27 mg, 95%).

Aufarbeitung

  1. extractionwhich was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0cebd8246aa43fcb1bf9294d1c184dd
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08158657B2

Notizen zur Reaktion

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