4-Methylmorpholine → HCID 53379822, Verbindung

HRID 1428918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428918
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CN1CCOCC1.[CH3:32][O:33][CH2:34][CH2:35][N:36]1[C:40]([CH3:41])=[C:39]([C:42]([OH:44])=O)[N:38]=[N:37]1.[CH3:45][NH:46][C:47]1[CH:52]=[CH:51][N:50]=[N:49][CH:48]=1>CN(C=O)C>[CH3:32][O:33][CH2:34][CH2:35][N:36]1[C:40]([CH3:41])=[C:39]([C:42]([N:46]([CH3:45])[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=2)=[O:44])[N:38]=[N:37]1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23080684N-methylpyridazin-4-amineHCID 62054042HCID 62054042, Verbindung

Produkt 1

HCID 53379822HCID 53379822, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphat (HATU; 1.23 g, 3.24 mmol, 3.00 eq) and N-methylmorpholine (0.71 ml, 0.66 g, 6.5 mmol, 6.0 eq) was added to a solution of 1-(2-methoxyethyl)-5-methyltriazole-4-carboxylic acid (200 mg, 1.08 mmol) and N-methylpyridazin-4-amine (118 mg, 1.08 mmol, 1.00 eq) in DMF (2.5 ml) and the mixture was stirred at room temperature for 4 d. After removal of the solvent, the residue was dissolved in dichloromethane, washed twice with sat. aq. NaHCO3 sol. and once with brine and dried over Na2SO4. Removal of the solvent under vacuum and chromatographic purification (CH:EtOAc) gave the title compound as a brown oil (200 mg, 64%, 95% purity).

Aufarbeitung

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed twice with sat. aq. NaHCO3 sol. and once with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent
  6. customunder vacuum and chromatographic purification (CH:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6a2dc1d44a664c058abd62ba700e2ac4
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937177B2

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