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Water → HCID 53932730, Verbindung

HRID 843157
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 843157
[OH:1][CH:2]([CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])[CH2:3][O:4][C:5]1[C:10]2[C:11]([CH3:17])=[C:12]([C:14]([OH:16])=O)[O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.Cl.[CH2:24]([NH2:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(N(CC)CC)C>[CH2:24]([NH:26][C:14]([C:12]1[O:13][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])[C:10]=2[C:11]=1[CH3:17])=[O:16])[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 22615054HCID 22615054, Verbindung

Produkt 1

HCID 53932730HCID 53932730, VerbindungAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid (5 mg), ethylamine hydrochloride (42 mg), water-soluble carbodiimide hydrochloride (10 mg), 1-hydroxybenzotriazole (8 mg) and triethylamine (100 μl) in DMF (1 ml) was stirred at room temperature for five hours. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH:H2O=65:30:5 as a developing solvent) to give 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethylamide (2 mg) as a white powder. MALDI-TOF-MS: m/z 335 (MH+); 1H-NMR (CDCl3): δ 1.27 (3H, t, J=7 Hz), 1.34 (6H, d, J=6 Hz), 2.72 (3H, s), 3.13 (1H, dd, J1=12 Hz, J2=9 Hz), 3.32 (2H, m), 3.49 (2H, dq, J1=7 Hz, J2=6 Hz), 4.05 (1H, dd, J1=10 Hz, J2=6 Hz), 4.15 (1H, dd, J1=10 Hz, J2=5 Hz), 4.53 (1H, br s), 6.55 (1H, d, J=8 Hz), 6.56 (1H, m), 7.00 (1H, d, J=8 Hz), 7.22 (1H, t, J=8 Hz).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by preparative thin layer chromatography (

Quellen und Nachweise

ORD-Eintrag
ord-90882fad6a81449ab01f1ac2826b1d88
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06376491B1

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