Acetylethanolamine → 6-(2-Acetylamino-ethoxy)-3-amino-5-chloro-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

HRID 656655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656655
[C:1]([NH:4][CH2:5][CH2:6][OH:7])(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:18]1([NH:21][C:22]([C:24]2[S:37][C:27]3=[N:28][C:29](S(C)=O)=[C:30]([Cl:33])[C:31]([CH3:32])=[C:26]3[C:25]=2[NH2:38])=[O:23])[CH2:20][CH2:19]1>C1COCC1>[CH:18]1([NH:21][C:22]([C:24]2[S:37][C:27]3=[N:28][C:29]([O:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[C:30]([Cl:33])[C:31]([CH3:32])=[C:26]3[C:25]=2[NH2:38])=[O:23])[CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 8880AcetylethanolamineHCID 2733832Lithium HexamethyldisilazideHCID 576644203-Amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Produkt 1

HCID 576644106-(2-Acetylamino-ethoxy)-3-amino-5-chloro-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-acetylethanolamine (1.120 g, 10.86 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes) (3.50 ml, 3.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 80° C. in a sealed tube for 1.5 hours, cooled to room temperature, and then quenched by the addition of water (15 ml). Ice is added to the reaction mixture and, while stirring, a yellow precipitate is formed. This solid is collected by filtration and placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a yellow solid (0.199 g, 52%). Mass (m/z): 383.2 (M++1), 381.1 (M+−1).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched by the addition of water (15 ml)
  3. additionIce is added to the reaction mixture
  4. stirringwhile stirring
  5. customa yellow precipitate is formed
  6. filtrationThis solid is collected by filtration
  7. customto dry (60° C. for 16 hours)

Quellen und Nachweise

ORD-Eintrag
ord-f17ec58c4e7c49f6a68af2555052fd4a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071776B2

Notizen zur Reaktion

Wird geladen…