Methyl iodide → HCID 59565476, Verbindung

HRID 1962866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962866
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:25][CH3:26])[C:15]([NH:17][C:18]([CH2:22][O:23][CH3:24])([CH3:21])[CH2:19][OH:20])=[O:16])=[CH:8][C:7]=2[CH3:27])#[CH:2].I[CH3:29].[H-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:25][CH3:26])[C:15]([NH:17][C:18]([CH2:19][O:20][CH3:29])([CH3:21])[CH2:22][O:23][CH3:24])=[O:16])=[CH:8][C:7]=2[CH3:27])#[CH:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 595653242-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

Produkt 1

HCID 59565476HCID 59565476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (120 mg) in dry THF (7 ml) NaH (19 mg, 60% in oil) was added at room temperature under a nitrogen atmosphere. After 30 minute iodomethane (30 □l) was added to the reaction mixture. After stirring during 5 h one equivalent of NaH and one equivalent of iodomethane were added. The mixture was stirred overnight at room temperature, then quenched with water and diluted with ethyl acetate. The water phase was extracted twice with ethyl acetate and the combined organic phases dried over sodium sulfate, filtered and evaporated. The crude residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane, 1:1:1) to give 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-methoxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (46 mg) as a light brown oil.

Aufarbeitung

  1. additionwere added
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. extractionThe water phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane, 1:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-767ca56a3b754e5f8c7483c1ad898d40
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415272B2

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