Tetrahydrofuran → (S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-C]pyridin-2(3H)-one

HRID 1014728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014728
[C:1]1([C@@H:7]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12](Br)[CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[C:25](Br)[C:24]([N+]([O-])=O)=[CH:23][N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1([C@@H](N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>C(OCC)(=O)C>[C:1]1([C@@H:7]([N:9]2[C:10]3[CH:11]=[C:12]([C:43]4[CH:42]=[CH:41][CH:40]=[C:23]5[C:24]=4[CH:25]=[CH:26][CH:21]=[N:22]5)[N:13]=[CH:14][C:15]=3[NH:16][C:50]2=[O:49])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 758181-Phenethylamine, (-)-HCID 81531DiisopropylethylamineHCID 160998502,4-Dibromo-5-nitropyridineHCID 86626410((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine

Produkt 1

HCID 24984682(S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-C]pyridin-2(3H)-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine. To a solution containing 2,4-dibromo-5-nitropyridine (500 mg, 1.75 mmol) and diisopropylethylamine (314 uL, 1.80 mmol) in tetrahydrofuran (8 mL) at 0° C. was added (S)-(−)-1-phenylethylamine (225 mg, 1.86 mmol). The reaction was allowed to come to room temperature and stirred for 18 h. The reaction was complete via LCMS and the solution was condensed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated to give the desired product (5.6 g, 99%). MS (ESI) m/z 322 [M+1]+.

Aufarbeitung

  1. customto come to room temperature
  2. customcondensed under reduced pressure
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2788e98dbc28453c81283d0a3e3d6f05
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981893B2

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