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Hydrochloric Acid → [2-[3-(2-fluoro-ethoxyimino)-2-oxo-2,3-dihydro-pyrrolo[2,3-b]pyridin-1-ylmethyl]-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 896343
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Druckvorschau

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Reaktionsgleichung von HRID 896343
[F:1][CH2:2][CH2:3][O:4][N:5]=[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:15].C([O-])([O-])=O.[Cs+].[Cs+].[C:22]([O:26][C:27](=[O:46])[NH:28][CH2:29][C:30]1[CH:45]=[CH:44][C:33]2[N:34]([CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])[C:35]([CH2:37]Cl)=[N:36][C:32]=2[CH:31]=1)([CH3:25])([CH3:24])[CH3:23].Cl>CN(C=O)C>[C:22]([O:26][C:27](=[O:46])[NH:28][CH2:29][C:30]1[CH:45]=[CH:44][C:33]2[N:34]([CH2:39][CH2:40][CH:41]([CH3:42])[CH3:43])[C:35]([CH2:37][N:8]3[C:9]4=[N:10][CH:11]=[CH:12][CH:13]=[C:14]4[C:6](=[N:5][O:4][CH2:3][CH2:2][F:1])[C:7]3=[O:15])=[N:36][C:32]=2[CH:31]=1)([CH3:23])([CH3:25])[CH3:24]
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 59561810HCID 59561810, VerbindungHCID 1363860121H-Pyrrolo[2,3-b]pyridine-2,3-dione 3-[O-(2-fluoro-ethyl)-oxime]

Produkt 1

HCID 86590116[2-[3-(2-fluoro-ethoxyimino)-2-oxo-2,3-dihydro-pyrrolo[2,3-b]pyridin-1-ylmethyl]-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester
Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1H-pyrrolo[2,3-b]pyridine-2,3-dione 3-[O-(2-fluoro-ethyl)-oxime] (23 mg, 0.11 mmol) in DMF (1.6 mL) was added Cs2CO3 (108 mg, 0.33 mmol). After stirring for 20 minutes, [2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester; HCl salt (44 mg, 0.11 mmol) was added and the resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic fractions washed with water, brine, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluant 1%, 5% MeOH in CH2Cl2) to give [2-[3-(2-fluoro-ethoxyimino)-2-oxo-2,3-dihydro-pyrrolo[2,3-b]pyridin-1-ylmethyl]-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (53 mg, 72%) as an off-white solid:

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic fractions washed with water, brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by flash chromatography (eluant 1%, 5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-549d3fc9d32d4af99b28508979c4d883
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06919331B2

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