3-(3-{4-[(6-Bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione → 3-(3-{4-[(6-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione

HRID 857111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857111
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:16]=[CH:17][CH:18]=1.ICCCCCCOCCC#CC1C=C(N2C(=O)CNC2=O)C=CC=1.[CH2:51]([NH:58][CH2:59][C@@H:60]([C:62]1[CH:73]=[CH:72][C:65]2[O:66][C:67]([CH3:71])([CH3:70])[O:68][CH2:69][C:64]=2[CH:63]=1)[OH:61])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C(#N)C.C(N(C(C)C)CC)(C)C>[CH2:51]([N:58]([CH2:59][C@@H:60]([C:62]1[CH:73]=[CH:72][C:65]2[O:66][C:67]([CH3:70])([CH3:71])[O:68][CH2:69][C:64]=2[CH:63]=1)[OH:61])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:16]=[CH:17][CH:18]=1)[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Komponenten

6

Edukt 3

HCID 218670753-(3-{4-[(6-Bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dioneHCID 218670893-(3-{4-[(6-Iodohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dioneHCID 69196697(1R)-2-(benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Produkt 1

HCID 693447783-(3-{4-[(6-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 3-(3-{4-[(6-bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione and 3-(3-{4-[(6-iodohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione (3:1, 23.98 g) in acetonitrile (240 ml) and diisopropylethylamine (20 ml) was treated with (1R)-2-(benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (18.22 g) and the mixture was heated to 50° C. for 5 days. The solvent was removed under reduced pressure, the residue was diluted with EtOAc (250 ml) and washed with water. The aqueous phase was re-extracted with EtOAc (75 ml) and the combined organic solutions were washed with brine, dried (MgSO4), and evaporated. The residue was purified by chromatography on flash silica gel eluting with dichloromethane-EtOAc (1:1) to give the title compound (17.25 g) LCMS RT=2.80 min

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (250 ml)
  3. washwashed with water
  4. extractionThe aqueous phase was re-extracted with EtOAc (75 ml)
  5. washthe combined organic solutions were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by chromatography on flash silica gel eluting with dichloromethane-EtOAc (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3db9163519014a07af2fbcc4bc48845f
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144908B2

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