1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-3-(3-((Dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-2-en-1-one

HRID 83030

Reaktionsgleichung

Reaktionsgleichung von HRID 83030
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][O:8][CH:9]1[CH2:12][NH:11][CH2:10]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:44][N:45]([CH2:47][C:48]1[C:56]2[C:51](=[N:52][CH:53]=[C:54](/[CH:57]=[CH:58]/[C:59](O)=[O:60])[CH:55]=2)[NH:50][CH:49]=1)[CH3:46]>CN(C)C=O>[CH3:44][N:45]([CH2:47][C:48]1[C:56]2[C:51](=[N:52][CH:53]=[C:54](/[CH:57]=[CH:58]/[C:59]([N:11]3[CH2:12][CH:9]([O:8][CH2:7][C:3]4[S:2][CH:6]=[CH:5][CH:4]=4)[CH2:10]3)=[O:60])[CH:55]=2)[NH:50][CH:49]=1)[CH3:46]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 671545443-(2-Thienylmethoxy)azetidine hydrochlorideHCID 70926878HCID 70926878, Verbindung

Produkt 1

HCID 52950703(E)-3-(3-((Dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(Thiophen-2-ylmethoxy)-azetidine hydrochloride (61 mg, 0.30 mmol), EDCI (71.5 mg, 0.37 mmol), HOBt (52 mg, 0.37 mmol) and diisopropylethylamine (110 μL, 0.62 mmol) were successively added to a solution of (E)-3-(3-((dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylic acid hydrochloride (70 mg, 0.25 mmol) in dimethylformamide (10 mL) at room temperature. The reaction mixture was stirred overnight then partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was separated, basified with an aqueous solution of sodium hydroxyde (2N) until pH 12 and finally extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulfate and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol/ammoniac (1:0:0.1 to 9:1:0.1) as eluent. The title product was obtained as a yellow solid (10 mg, 10%).

Aufarbeitung

  1. customthen partitioned between ethyl acetate (30 mL) and water (30 mL)
  2. customThe aqueous layer was separated
  3. extractionfinally extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e39f36dbb045417292916c9bd246c6b5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846711B2

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