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 1181978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181978
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.ON1C2C=CC=CC=2N=N1.[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 757711-HydroxybenzotriazoleHCID 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-one

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-hydroxybenztriazole (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-ba2b8663bc1d4bcb9c71360394f0598a
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285662B2

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