Sodium Carbonate → 1-(2-{4-[7-(5-(Aminomethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl]-5-fluoropyrimidin-2-ylamino}ethyl)imidazolidin-2-one

HRID 561036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561036
[N:1]([CH2:4][C:5]1[C:6]([C:12]2[C:17]3[S:18][C:19]([C:21]4[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:28][CH2:29][CH2:30][N:31]5[CH2:35][CH2:34][NH:33][C:32]5=[O:36])[N:22]=4)=[CH:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[CH:7][C:8]([F:11])=[N:9][CH:10]=1)=[N+]=[N-].C(O)=O.NN.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[Ni]>[NH2:1][CH2:4][C:5]1[C:6]([C:12]2[C:17]3[S:18][C:19]([C:21]4[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:28][CH2:29][CH2:30][N:31]5[CH2:35][CH2:34][NH:33][C:32]5=[O:36])[N:22]=4)=[CH:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[CH:7][C:8]([F:11])=[N:9][CH:10]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 46899473Hy-drazinium monoformateHCID 86640496HCID 86640496, Verbindung

Produkt 1

HCID 249368481-(2-{4-[7-(5-(Aminomethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl]-5-fluoropyrimidin-2-ylamino}ethyl)imidazolidin-2-oneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-{4-[7-(5-azidomethyl-2-fluoro-pyridin-4-yl)-benzo[b]thiophen-2-yl]-5-fluoro-pyrimidin-2-ylamino}-ethyl)-imidazolidin-2-one (105 mg, 0.3 mmol) in ethanol (10 mL) in a round bottom flask add 2 g hydrazine formic acid salt (1:1) and 0.5 g of Raney Nickel. Stir the mixture for 3 hours at room temperature. Pour the reaction mixture diluted sodium carbonate solution. Abstract the product into chloroform, and wash with water and saturated aqueous sodium chloride. Separate organic layer from aqueous layer and dry over Na2SO4. After filtration, evaporate the organic solvent in vacuo to give a crude product. Purify the crude with flash column chromatography (chloroform/methanol/ammonium hydroxide, 7/3/0.05) to give the title compound as a yellow solid (0.50 mg, 53%). MS (ES) m/z 482 [M+1]+.

Aufarbeitung

  1. washAbstract the product into chloroform, and wash with water and saturated aqueous sodium chloride
  2. dry with materialSeparate organic layer from aqueous layer and dry over Na2SO4
  3. filtrationAfter filtration
  4. customevaporate the organic solvent in vacuo
  5. customto give a crude product
  6. customPurify the crude with flash column chromatography (chloroform/methanol/ammonium hydroxide, 7/3/0.05)

Quellen und Nachweise

ORD-Eintrag
ord-420562fa808942faa992801d52d0a66f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063212B2

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