Tert-Butylamine → N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

HRID 1962853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962853
[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:18][CH3:19])[C:15]([OH:17])=O)=[CH:8][CH:7]=2)#[CH:2].[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>[C:20]([NH:24][C:15](=[O:17])[CH:14]([O:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]2)[S:18][CH3:19])([CH3:23])([CH3:22])[CH3:21]

Komponenten

9

Edukt 4

HCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59565474(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid

Produkt 1

HCID 59565325N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 181649HOAtKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (1.1 g), N-tert-Butyl amine (0.467 ml), 1-hydroxy-7-azabenzotriazole (HOAT) (0.602 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCl) (849 mg) and triethylamine (0.84 ml) in dry N,N-dimethylformamide (20 ml) were stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and poured on 60 ml aq. sat. sodium hydrogen carbonate. The water phase was extracted with 3×150 ml ethyl acetate. All organic layers were combined, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 13:7) to give N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.11 g) as yellowish solid.

Aufarbeitung

  1. extractionThe water phase was extracted with 3×150 ml ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (heptane/ethyl acetate 13:7)

Quellen und Nachweise

ORD-Eintrag
ord-b69284d9e63246f588a556c8d1ce4bb4
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415272B2

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