N,N-Dimethylethylenediamine → N-(2-(dimethylamino)ethyl)-8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 572741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572741
[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.[OH:21][CH:22]([C:24]1[CH:25]=[C:26]([C:41]([OH:43])=O)[CH:27]=[C:28]2[C:33]=1[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])[CH3:23].CCN(C(C)C)C(C)C.[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH2:57]>C(Cl)Cl>[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH:57][C:41]([C:26]1[CH:27]=[C:28]2[C:33](=[C:24]([CH:22]([OH:21])[CH3:23])[CH:25]=1)[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])=[O:43]

Komponenten

6

Edukt 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 582349808-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Produkt 1

HCID 58235055N-(2-(dimethylamino)ethyl)-8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamideAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

TSTU (104 mg, 0.34 mmol) at 25° C., was added portionwise to 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (110 mg, 0.34 mmol) and DIPEA (0.066 mL, 0.38 mmol) suspended in DCM (1 mL) under nitrogen. The resulting mixture was stirred at 25° C. for 1.5 hrs. N1,N1-dimethylethane-1,2-diamine (0.038 mL, 0.34 mmol) was then added and the mixture stirred at 25° C. for 30 minutes. The mixture was poured onto a silica gel column and purified by flash chromatography eluting with 5% methanolic ammonia (7 N) in DCM. The solvent was evaporated to dryness, the residue was triturated in diethyl ether, collected by filtration and dried to afford N-(2-(dimethylamino)ethyl)-8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide (80 mg, 0.205 mmol, 59.6%) as a off-white solid. Mass Spectrum: M+H+ 390.

Aufarbeitung

  1. stirringthe mixture stirred at 25° C. for 30 minutes
  2. additionThe mixture was poured onto a silica gel column
  3. custompurified by flash chromatography
  4. washeluting with 5% methanolic ammonia (7 N) in DCM
  5. customThe solvent was evaporated to dryness
  6. customthe residue was triturated in diethyl ether
  7. filtrationcollected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1e21450db5c6463eae4ddf5908ea577a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029374B2

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