Acetic Anhydride → HCID 59140179, Verbindung

HRID 1500704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500704
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH2:24])=[CH:7][N:6]=1)=[O:4].[C:25](OC(=O)C)(=[O:27])C>C(O)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:20])[CH3:21])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH:24][CH:25]=[O:27])=[CH:7][N:6]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 591401895-Aminomethyl-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

Produkt 1

HCID 59140179HCID 59140179, VerbindungAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A solution of 5-aminomethyl-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester (800 mg, 2.30 mmol) from above in formic acid (12 mL) and acetic anhydride (4 mL) was stirred at ambient temperature under N2 for 1.5 hour. The reaction mixture was concentrated in vacuo, and the residue was azeotroped with toluene. The resultant residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate, water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a yellow foam (850 mg, 98.3%). LCMS (method D1): RT=1.09 min, [M+H]+=377.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was azeotroped with toluene
  3. additionThe resultant residue was diluted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate, water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9a08d281b8c456d81a6662b93665d67
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206174B2

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