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Ethanolamine → HCID 57736468, Verbindung

HRID 1641738
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641738
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([OH:18])=O)=[N:14][CH:15]=1.[NH2:28][CH2:29][CH2:30][OH:31].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20][C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:28][CH2:29][CH2:30][OH:31])=[O:18])=[N:14][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57736444HCID 57736444, Verbindung

Produkt 1

HCID 57736468HCID 57736468, Verbindung
Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[(2,5-difluorophenyl) [(4-fluorophenyl)thio]methyl]-4-meth ylpyridine-2-carboxylic acid (483 mg, 1.24 mmol) obtained in Example 20 in methylene chloride (10 ml), 2-aminoethanol (0.083 ml, 1.36 mmol), 1-hydroxybenzotriazole (184 mg, 1.36 mmol), 4-methylmorpholine (0.150 ml, 1.36 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (262 mg, 1.36 mmol) were added at room temperature. After stirring for 4 hours at room temperature, water was added to the reaction mixture, and the mixture was washed with saturated aqueous ammonium chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:3 was concentrated under reduced pressure, to obtain the title compound (481 mg, 1.11 mmol, 90%) as a colorless foamy substance.

Aufarbeitung

  1. washthe mixture was washed with saturated aqueous ammonium chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=1:3 was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c458e2e1b0fe42c1a94ab63be06b5106
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114886B2

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