1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(6-quinolinyloxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide

HRID 1244804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244804
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:16][CH3:17])[C:13]([OH:15])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:18][C:19]([CH3:32])([CH3:31])[C:20]#[C:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].Cl.CN(C)CCCN=C=NCC.CCCCCC.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:16][CH3:17])[C:13]([NH:18][C:19]([CH3:32])([CH3:31])[C:20]#[C:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])=[O:15])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226206Ethyl acetate hexaneHCID 219231162-(6-Quinolinyloxy)butyric acidHCID 219231344-Amino-1-tert-butyldimethylsilyloxy-4-methylpent-2-yne

Produkt 1

HCID 219231372-(6-quinolinyloxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramideAusbeute 10,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-(6-Quinolinyloxy)butyric acid (0.61 g), 4-amino-1-tert-butyldimethylsilyloxy-4-methylpent-2-yne (0.57 g) and 4-dimethylaminopyridine (0.010 g) in dry dichloromethane (10 ml) were stirred and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.53 g) was added. The mixture was stirred at ambient temperature for 3.5 hours, stored for 2 days, diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate (twice) and then with water. The organic phase was dried over magnesium sulphate and evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 3:1 by volume) to give a gum that was triturated with hexane to give the required product (0.12 g) as a colourless solid, m.p. 78–80° C.

Aufarbeitung

  1. waitstored for 2 days
  2. washwashed with saturated aqueous sodium hydrogen carbonate (twice) and then with water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow oil
  6. customto give a gum that
  7. customwas triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-3839cb092e7449049e20618601ebb118
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122672B2

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