Benzenamine, 4-(4-morpholinyl)- → 6-Methoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

HRID 1795349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795349
COC1C=CC=CC=1N1CC[N:12]([C:15]([C:17]2[O:18][C:19]3[C:24]([C:25](=[O:27])[CH:26]=2)=[CH:23][CH:22]=[CH:21][C:20]=3[N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[O:16])CC1.CN([C:38]([O:42]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.OS1C2C=CC=CC=2N=C1.[N:67]1([C:73]2[CH:79]=[CH:78][C:76](N)=[CH:75][CH:74]=2)[CH2:72][CH2:71][O:70][CH2:69][CH2:68]1>CN(C)C1C=CN=CC=1.CN(C)C=O.C(N(CC)CC)C>[N:67]1([C:73]2[CH:79]=[CH:78][C:76]([NH:12][C:15]([C:17]3[O:18][C:19]4[C:24]([C:25](=[O:27])[CH:26]=3)=[CH:23][C:22]([O:42][CH3:38])=[CH:21][C:20]=4[N:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)=[O:16])=[CH:75][CH:74]=2)[CH2:72][CH2:71][O:70][CH2:69][CH2:68]1

Komponenten

8

Edukt 4

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 101396012-{1-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-methanoyl}-8-(4-methyl-piperazin-1-yl)-chromen-4-oneHCID 178527226HCID 178527226, Verbindung

Produkt 1

HCID 235333236-Methoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

6-Methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 2) (3.0 g, 8.5 mmol), TBTU (5.5 g, 17 mmol), 1-hydroxybenzothiazole (2.6 g, 17 mmol), 4-dimethylaminopyridine (0.05 g, catalytic) and commercially available 4-morpholin-4-yl-aniline (1.66 g, 9.3 mmol) were dissolved in dimethylformamide (100 mL). Triethylamine (3.5 mL, 25 mmol was added and this mixture stirred at room temperature for 17 hours. The reaction mixture was concentrated under vacuum and the residue was partitioned between chloroform (400 mL) and saturated aqueous sodium bicarbonate (50 mL). The organic layer was separated, dried (Na2SO4), vacuum-filtered and concentrated under vacuum. The residue was purified by chromatography on silica eluted with 2–5% methanol in chloroform and then triturated with ether to yield a yellow powder. (1.6 g=39%) LCMS−m/z=479.5 mp=234–236° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was partitioned between chloroform (400 mL) and saturated aqueous sodium bicarbonate (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationvacuum-filtered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica
  8. washeluted with 2–5% methanol in chloroform
  9. customtriturated with ether
  10. customto yield a yellow powder

Quellen und Nachweise

ORD-Eintrag
ord-12beffe6ef224f009d4b99643293b1c0
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026314B2

Notizen zur Reaktion

Wird geladen…