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Oxalyl chloride → (E)-4,4,4-Trifluoro-N-[2-(furo[3,2-b]pyridin-7-ylamino)-2-oxo-ethyl]but-2-enamide

HRID 333087
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333087
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.Cl.[NH2:17][CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[CH:29][O:30][C:23]=12)=[O:20].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5]([NH:17][CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[CH:29][O:30][C:23]=12)=[O:20])=[O:6]
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Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 668353512-Amino-N-furo[3,2-b]pyridin-7-yl-acetamide hydrochloride

Produkt 1

HCID 56947336(E)-4,4,4-Trifluoro-N-[2-(furo[3,2-b]pyridin-7-ylamino)-2-oxo-ethyl]but-2-enamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(E)-4,4,4-Trifluorobut-2-enoic acid (15.4 mg, 0.11 mmol) was dissolved in DCM (0.75 ml containing one drop of dimethyl formamide), oxalyl chloride was added (14 mg, 0.11 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 2-amino-N-furo[3,2-b]pyridin-7-yl-acetamide hydrochloride (25.3 mg, 0.11 mmol) and diisopropylethylamine (44 μl, 0.25 mmol) dissolved in dimethylformamide (1 ml) and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 6.9 mg (0.022 mmol, 20%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  4. customto yield 6.9 mg (0.022 mmol, 20%)

Quellen und Nachweise

ORD-Eintrag
ord-e2c379de5d714d4094c86493a3900f9a
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877934B2

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