4-[2-(4-Fluoro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid tert-butyl ester → 4-[2-(4-Fluoro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid

HRID 1915693

Reaktionsgleichung

Reaktionsgleichung von HRID 1915693
C([O:5][C:6]([C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:32]=[CH:31][C:18]3[N:19]([CH3:30])[C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[N:21][C:17]=3[CH:16]=2)[CH:11]=[CH:10][N:9]=1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O.O>[F:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20]2[N:19]([CH3:30])[C:18]3[CH:31]=[CH:32][C:15]([O:14][C:12]4[CH:11]=[CH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:13]=4)=[CH:16][C:17]=3[N:21]=2)=[CH:24][CH:25]=1

Komponenten

4

Edukt 1

HCID 210373684-[2-(4-Fluoro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 220412944-[2-(4-Fluoro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A stirring solution of 4-[2-(4-Fluoro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid tert-butyl ester in trifluoroacetic acid was treated with two drops of water at room temperature for 3-4 hours or when the reaction was determined to be complete by HPLC. The reaction was evaporated under reduced pressure and then ether was added to the residue, which was then sonicated for 30 minutes. Filtration and washing with ether yields the desired acid in quantitative yield. LCMS m/z 379.4 (MH+), tR=1.74 mm.

Aufarbeitung

  1. customThe reaction was evaporated under reduced pressure
  2. additionether was added to the residue, which
  3. customwas then sonicated for 30 minutes
  4. filtrationFiltration
  5. washwashing with ether

Quellen und Nachweise

ORD-Eintrag
ord-2e43236960ea4cc1b265a047d7234db3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614330B2

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