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Hydrogen Sulfide → N-(4-Chlorophenyl)-3-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-4-carboxamide

HRID 2083932
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2083932
Cl[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:9].[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][CH:27]([CH2:30][NH2:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.S>CN(C)C=O.CO.[Cu]Br>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8]([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[NH:31][CH2:30][CH:27]2[CH2:26][CH2:25][N:24]([C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH2:29][CH2:28]2)=[O:9])=[CH:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 402Hydrogen SulfideHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamineHCID 121506913-chloro-N-(4-chlorophenyl)pyridine-4-carboxamide

Produkt 1

HCID 12150692N-(4-Chlorophenyl)-3-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-4-carboxamideAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24593
copper(I) bromide
Katalysator
HCID 887MethanolLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 3-chloro-N-(4-chlorophenyl)pyridine-4-carboxamide (130 mg, 0.49 mmol), 1-(4-pyridyl)piperidine-4-methylamine (187 mg, 0.98 mmol), and copper(1) bromide (70 mg) in dimethylformamide (1 mL) was heated at 110° C. After 18 h, the mixture was diluted with MeOH, filtered, and concentrated. The residue was treated with 6:1 chloroform:water (10 mL) followed by MeOH until a homogenoeus solution resulted. The solution was treated with hydrogen sulfide(g), heated at reflux for 0.1 h, and filtered through diatomaceous earth. The filtrate was concentrated and the residue taken up in water, 1 N NaOH, and EtOAc. The aqueous layer was washed with EtOAc (3×), the combined extracts were dried (sodium sulfate), filtered and concentrated. The residue was purified by RPHPLC yielding 29 mg (13%) of the title compound as a hydrochloride salt.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe residue was treated with 6:1 chloroform
  4. customresulted
  5. temperatureheated
  6. temperatureat reflux for 0.1 h
  7. filtrationfiltered through diatomaceous earth
  8. concentrationThe filtrate was concentrated
  9. washThe aqueous layer was washed with EtOAc (3×)
  10. dry with materialthe combined extracts were dried (sodium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by RPHPLC

Quellen und Nachweise

ORD-Eintrag
ord-b94dbdaab26544aa9191122b8ec7bc26
Quelldatensatz
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06716839B2

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