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Cesium carbonate → 3-[4-({3-[1-(N,N-dimethylglycyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}methyl)-pyridin-2-yl]-1,1-dimethylurea

HRID 546609
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546609
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]([CH3:33])([CH3:32])[CH2:22][N:23]4[C:26](=[O:31])[CH2:27][N:28]([CH3:30])[CH3:29])=[CH:19][CH:18]=3)[C:10]2=[O:34])[CH:5]=[CH:4][N:3]=1.[CH3:35][N:36]([CH3:40])[C:37]([NH2:39])=[O:38].CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][N:28]([CH3:30])[CH2:27][C:26]([N:23]1[C:24]2[C:20](=[CH:19][CH:18]=[C:17]([N:11]3[C:12](=[O:16])[C:13]([CH3:15])([CH3:14])[N:9]([CH2:8][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:39][C:37](=[O:38])[N:36]([CH3:40])[CH3:35])[CH:7]=4)[C:10]3=[O:34])[CH:25]=2)[C:21]([CH3:33])([CH3:32])[CH2:22]1)=[O:31]
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Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 11737N,N-DimethylureaHCID 576260011-(2-chloropyridin-4-ylmethyl)-3-[1-(2-dimethylamino-acetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-imidazolidine-2,4-dioneHCID 86628973(9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)

Produkt 1

HCID 57625976
3-[4-({3-[1-(N,N-dimethylglycyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}methyl)-pyridin-2-yl]-1,1-dimethylurea
Ausbeute 19,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 242 mg of 1-(2-chloropyridin-4-ylmethyl)-3-[1-(2-dimethylamino-acetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-imidazolidine-2,4-dione obtained in stage a) of Example 31B in 10 mL of dioxane are successively added, under argon, 33 mg of N,N-dimethylurea, 29 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (Xantphos), 22 mg of palladium acetate and 652 mg of caesium carbonate. The reaction mixture is refluxed for 6 hours, cooled to room temperature, filtered and washed with three times 10 mL of dichloromethane, and the filtrate is concentrated under reduced pressure. The residue is triturated in 20 mL of water and the precipitate formed is filtered off and purified twice by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (93/7 by volume) to give 40 mg of 3-[4-({3-[1-(N,N-dimethylglycyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}methyl)-pyridin-2-yl]-1,1-dimethylurea, the characteristics of which are as follows:

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. filtrationfiltered
  3. washwashed with three times 10 mL of dichloromethane
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is triturated in 20 mL of water
  6. customthe precipitate formed
  7. filtrationis filtered off
  8. custompurified twice by chromatography on a column of silica
  9. washeluting with a mixture of dichloromethane and methanol (93/7 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-f96d97cfd9c345ddbe11d4bc0db1668e
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935819B2

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