Triethylamine → HCID 57786339, Verbindung

HRID 1628605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628605
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH2:22][C:23](O)=[O:24])[C:6]=2[C:5]([CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>CN(C)C=O.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:12]4[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=4[O:20][CH3:21])[C:23](=[O:24])[CH2:22][N:7]3[C:6]=2[C:5]([CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58012318HCID 58012318, Verbindung

Produkt 1

HCID 57786339HCID 57786339, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of [4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetic acid (Reference Example 13; 770 mg, 1.71 mmol) in N,N-dimethylformamide (6 mL) was added HOBt (288 mg, 1.88 mmol), triethylamine (0.595 mL, 4.28 mmol) and WSC (426 mg, 2.22 mmol), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (×2). The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate and brine (×2), dried over sodium sulfate and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 10-25% ethyl acetate/n-hexane gradient mixture to give the crude title compound as an oil. The oil was crystallized from diisopropyl ether-n-hexane to give the title compound (519 mg, 1.20 mmol, 70%) as a colorless crystal.

Aufarbeitung

  1. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate and brine (×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by basic silica gel column chromatography
  6. washeluting with a 10-25% ethyl acetate/n-hexane gradient mixture
  7. customto give the crude title compound as an oil
  8. customThe oil was crystallized from diisopropyl ether-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1ad04a400bc943a08ca113bb456e9baf
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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