Ammonia → HCID 66726154, Verbindung

HRID 1042110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042110
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([OH:30])=O)=[CH:15]3)=[N:9][CH:10]=1)(=[O:4])=[O:3].Cl.C[N:33](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.N>CN(C)C=O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([NH2:33])=[O:30])=[CH:15]3)=[N:9][CH:10]=1)(=[O:3])=[O:4]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667259135-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid

Produkt 1

HCID 66726154HCID 66726154, VerbindungAusbeute 27,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid (2.5 g), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.2 g), 1-hydroxybenzotriazole (1.6 g), and N,N-dimethylformamide (25 mL) was stirred at 50° C. for 30 min. The reaction mixture was cooled to room temperature, 10% aqueous ammonia (4 mL) was added and the mixture was stirred at room temperature for 1.5 hr. The reaction solution was concentrated under reduced pressure, water was added to the residue, and ethyl acetate-tetrahydrofuran was added. The precipitated solid was collected by filtration to give the title compound (0.69 g) as a pale-yellow solid. The filtrate was concentrated under reduced pressure to evaporate the organic solvent. The precipitate was collected by filtration to give the title compound (0.72 g) as a pale-yellow solid (total yield 1.41 g, 64%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 1.5 hr
  3. concentrationThe reaction solution was concentrated under reduced pressure, water
  4. additionwas added to the residue, and ethyl acetate-tetrahydrofuran
  5. additionwas added
  6. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-072c30ff3904413ca958b8d00876fea0
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557805B2

Notizen zur Reaktion

Wird geladen…