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Morpholine → HCID 68456406, Verbindung

HRID 2357655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357655
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1)#[N:2].[OH-].[K+].N1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CN(C([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCO.O.C(OCC)(=O)C>[CH:19]1([NH:18][C:16](=[O:17])[C:15]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:13]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[C:3]([C:1]([N:2]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:41])=[N:4][N:5]=[CH:6]4)[CH:14]=2)[CH2:20][CH2:21]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 14797Potassium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68452746HCID 68452746, Verbindung

Produkt 1

HCID 68456406HCID 68456406, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-(1-Cyanophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (115 mg, 350 μmol) was dissolved in EtOH/water (1:1) (3.50 mL) with potassium hydroxide (39 mg, 700 μmol) and heated in a microwave oven for 15 min at 120° C. The reaction mixture was concentrated in vacuo and dissolved in DMF (700 μl) and morpholine (152 μl, 1751 μmol) to which HATU (399 mg, 1051 μmol) was added. The reaction was stirred at RT for 16 h, then diluted with ethyl acetate, filtered, diluted with 50 mL ethyl acetate, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 2×20 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography to give the title compound. MS (ES+): 417 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in DMF (700 μl)
  3. filtrationfiltered
  4. additiondiluted with 50 mL ethyl acetate
  5. custompartitioned with sodium bicarbonate (saturated, aqueous)
  6. washThe organic layers were washed 2×20 mL with sodium bicarbonate (saturated, aqueous)
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7b2d9d0804554d5f8a83bee72b8ab60d
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759337B2

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