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

1-tert-Butyl-3-methyl-1H-pyrazole-5-carbonyl chloride → 2-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 2352853
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2352853
[C:1]([N:5]1[C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]([CH3:13])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:32]=[CH:31][C:18]([C:19]([C:21]2[CH:29]=[C:28]3[C:24]([CH2:25][C:26](=[O:30])[NH:27]3)=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1>C1COCC1>[O:30]=[C:26]1[CH2:25][C:24]2[C:28](=[CH:29][C:21]([C:19]([C:18]3[CH:17]=[CH:16][C:15]([NH:14][C:10]([C:9]4[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]=[C:7]([CH3:13])[CH:8]=4)=[O:11])=[CH:32][CH:31]=3)=[O:20])=[CH:22][CH:23]=2)[NH:27]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 27993401-tert-Butyl-3-methyl-1H-pyrazole-5-carbonyl chlorideHCID 592564856-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 866103952-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A dry 25 mL flask was charged with 2-tert-Butyl-5-methyl-2H-pyrazole-3-carbonyl chloride (1.03 g, 5.17 mmol) and THF (10 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 15, 1.0 g, 3.97 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 4 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford the pure 2-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.654 g, 1.68 mmol, 42%).

Aufarbeitung

  1. temperatureto reflux for 4 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionthe crude residue was dissolved in EtOH (5 mL)
  5. additionThe ethanolic solution was treated with 1M NaOH(aq) (2 mL)
  6. customyielding a tan precipitate
  7. filtrationThe tan solids were filtered

Quellen und Nachweise

ORD-Eintrag
ord-90f200db1dfc44b0af8e2815db099d8f
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07749530B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion