Potassium Carbonate → HCID 178497723, Verbindung

HRID 1488076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488076
Br[CH:2]([CH3:16])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=O.Cl.[N:18]1([C:23](=[NH:25])[NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O>[CH3:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:3]1[NH:25][C:23]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:24][C:2]=1[CH3:16]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 13221241Pyrrolidine-1-carboximidamide hydrochloride2×HCID 90021391Methyl 3-(2-bromopropanoyl)-4-methylbenzoate2×

Produkt 1

HCID 178497723HCID 178497723, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Into a 50-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(2-bromopropanoyl)-4-methylbenzoate (compound 197.2, 500.0 mg, 1.75 mmol) in N,N-dimethylformamide (15 mL). Pyrrolidine-1-carboximidamide hydrochloride (compound 197.1, 260.8 mg, 1.75 mmol) was treated with K2CO3, then added to the reaction. The reaction mixture was stirred for 1 h at 50° C. The reaction mixture was diluted with 30 mL of H2O. The aqueous phase was extracted with 3×30 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with PE/EtOAc (1:1)˜EtOAc/methanol (15:1) as eluent to furnish 230.0 mg (44%) of the title compound as a dark blue solid.

Aufarbeitung

  1. customInto a 50-mL round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionadded to the reaction
  4. extractionThe aqueous phase was extracted with 3×30 mL of ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography with PE/EtOAc (1:1)˜EtOAc/methanol (15:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ff089136d27c46f3b418f5318fea5230
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428502B2

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