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

Triethylamine → 1-(4-Chlorophenyl)-n-(5-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

HRID 870007
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 870007
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C[O:19][C:20]1[N:25]=[CH:24][C:23]([C:26]2[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]([NH2:33])[N:27]=2)=[CH:22][C:21]=1[CH3:34].C(N(CC)CC)C>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([NH:33][C:28]3[CH:29]=[CH:30][C:31]([CH3:32])=[C:26]([C:23]4[CH:22]=[C:21]([CH3:34])[C:20](=[O:19])[NH:25][CH:24]=4)[N:27]=3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 68722468HCID 68722468, Verbindung

Produkt 1

HCID 710530451-(4-Chlorophenyl)-n-(5-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamideAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (39.3 mg, 0.2 mmol) in dichloromethane (2 mL) was added thionyl chloride (43.8 μL, 0.6 mmol) followed by DMF (1 drop) and the reaction was stirred at room temperature for 30 minutes and then the solvent was removed. Toluene (˜1 mL) was added, mixed with the residue and then removed by evaporation. The residue was then dissolved in dichloromethane (1 mL) and a solution of 6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-amine (46 mg, 0.2 mmol) and triethyl amine (83.6 μL, 0.60 mmol) in dichloromethane (1 mL) was added. The reaction was stirred at room temperature for 12 hors. The reaction was then concentrated. The residue was dissolved in DMSO and purified by reverse phase HPLC (10-99% acetonitrile/water) to yield 62 mg of the product. ESI-MS m/z calc. 407.1. found 408.2 (M+1)+. Retention time 2.07 minutes.

Aufarbeitung

  1. customthe solvent was removed
  2. additionToluene (˜1 mL) was added
  3. additionmixed with the residue
  4. customremoved by evaporation
  5. dissolutionThe residue was then dissolved in dichloromethane (1 mL)
  6. stirringThe reaction was stirred at room temperature for 12 hors
  7. concentrationThe reaction was then concentrated
  8. dissolutionThe residue was dissolved in DMSO
  9. custompurified by reverse phase HPLC (10-99% acetonitrile/water)

Quellen und Nachweise

ORD-Eintrag
ord-7c2ae0741bdf4151ad65887395542f20
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969386B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion