StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Methanol → HCID 58190476, Verbindung

HRID 1892410
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1892410
O=[C:2]1[C:10]2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C:14]([NH2:16])=[O:15].O.NN.CO.[N:22]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][C:33]3[N:37]4[N:38]=[C:39](C(=O)C)[CH:40]=[CH:41][C:36]4=[N:35][N:34]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1>C(O)(=O)C>[N:22]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][C:33]3[N:37]4[N:38]=[C:39](/[C:2](=[N:3]/[O:12][CH2:13][C:14]([NH2:16])=[O:15])/[CH3:10])[CH:40]=[CH:41][C:36]4=[N:35][N:34]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 140744182-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetamide2×HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Produkt 1

HCID 58190476HCID 58190476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A microwave tube was charged with 2-(1,3-dioxoisoindolin-2-yloxy)acetamide (intermediate V) (166 mg, 0.76 mmol), hydrazine monohydrate (34.4 mg, 0.69 mmol) and 2 mL of methanol. It was heated at 95° C. for 12 h under microwave irradiation. After cooling, solid was removed by filtration and the solution was concentrated under reduced pressure. The residue was diluted with methanol, then 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (32 mg, 0.105 mmol) and 0.3 mL of acetic acid were added and the mixture was stirred at 40° C. overnight. After concentration, the residue was purified by prep-HPLC to afford the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.86 (dd, 1H), 8.33-8.27 (m, 2H), 7.98-7.95 (m, 2H), 7.78 (dd, 1H), 7.69 (d, 1H), 7.50 (dd, 1H), 7.31 (d, 2H), 4.77 (s, 2H), 4.63 (s, 2H), 2.32 (s, 3H). LCMS (method A): [MH]+=376, tR=4.02 min.

Aufarbeitung

  1. temperatureAfter cooling
  2. customsolid was removed by filtration
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionThe residue was diluted with methanol
  5. concentrationAfter concentration
  6. customthe residue was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2f8cfdcbaaf74db48974029e9110f9d2
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507676B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion