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 2070316Notes

Reaction equation

HRID 2070316 reaction equation
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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

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 min.

Workup

  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

Sources & evidence

ORD record
ord-4ac06553c0bd46d1ada0a9b87d2b268c
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

Loading…