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Triethylamine → 3-(3-(3-Butoxy-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamine

HRID 1691217
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1691217
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13](Cl)=[N:14][OH:15])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].[C:17]([C:19]1[C:20]([NH2:26])=[N:21][C:22]([NH2:25])=[CH:23][CH:24]=1)#[CH:18].C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][C:13]1[CH:18]=[C:17]([C:19]2[C:20]([NH2:26])=[N:21][C:22]([NH2:25])=[CH:23][CH:24]=2)[O:15][N:14]=1)[CH2:2][CH2:3][CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262884HCID 72262884, Verbindung

Produkt 1

HCID 592554013-(3-(3-Butoxy-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamineAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran (3 mL) solution of (3-butoxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.621 mmol) described in Manufacturing Example 65-1-4 and 3-ethynyl-pyridin-2,6-diamine (52.8 mg, 0.396 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (216 μL, 1.55 mmol). This mixture was stirred for 4 hours at room temperature. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water and 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:heptane=1:1˜ethyl acetate) to obtain the title compound (43 mg, 21%).

Aufarbeitung

  1. customThe mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and 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:heptane=1:1˜ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6f280df7dce245009756a24f0bb2b689
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08153662B2

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