Triethylamine → HCID 57629423, Verbindung

HRID 2108883

Reaktionsgleichung

Reaktionsgleichung von HRID 2108883
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>C(Cl)(Cl)Cl.O>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)=[O:29]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 5211735-Bromovaleryl chlorideHCID 27359604-Amino-7-(trifluoromethyl)quinoline

Produkt 1

HCID 57629423HCID 57629423, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4-Amino-7-trifluoromethylquinoline (120 mg, 0.56 mmol), triethylamine (170 mg, 1.7 mmol) and CHCl3 (4 mL) were charged in a 10 ml round-bottomed flask equipped with a magnetic stirrer. 5-Bromovaleryl chloride (140 mg, 0.7 mmol in CHCl3 (2 mL) were added and the reaction mixture was stirred for 15 h at 20° C. The reaction mixture was poured in 10 mL of H2O and extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (2×10 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 98:2) to give after evaporation 5-bromo-N-(7-(trifluoromethyl)quinolin-4-yl)pentanamide 32 (190 mg, 90% yield) as a beige solid.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. extractionextracted with CH2Cl2 (100 mL)
  3. washThe organic layer was washed with brine (2×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated at 30° C. to dryness
  7. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 98:2)
  8. customto give

Quellen und Nachweise

ORD-Eintrag
ord-f75ee1d4f13044f584c5438a19a7d8f4
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514432B2

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