Trifluoroacetic acid → HCID 67358297, compound

HRID 1185997Notes

Reaction equation

HRID 1185997 reaction equation
C([O:5][C:6]([CH2:8][C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:28]=[CH:27][C:22](C(OC)=O)=[CH:21][CH:20]=1)=[O:7])(C)(C)C.F[C:30](F)(F)[C:31]([OH:33])=[O:32]>ClCCl>[C:31]([CH2:30][C:22]1[CH:21]=[CH:20][C:19]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]3[C:9]=2[CH2:8][C:6]([OH:5])=[O:7])=[CH:28][CH:27]=1)([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67359527HCID 67359527, compound

Product 1

HCID 67358297HCID 67358297, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10 (3.1 g, 8.15 mmol) in dichloromethane (50 ml) was added to trifluoroacetic acid (25 ml). Following stirring at room temperature for 2 h the solution was concentrated to dryness. Potassium carbonate (10%) solution (100 ml) was added and the solution washed with diethyl ether (2×50 ml) and acidified to pH 6 with HCl (6M). The precipitate was filtered, washed with diethyl ether and recrystallized to give [2-(4-carboxymethylphenyl)-6-methylimidazo[1,2-a]pyridin-3-yl]acetic acid 11 as a white solid (1.65 g, 62%).

Workup

  1. concentrationwas concentrated to dryness
  2. additionPotassium carbonate (10%) solution (100 ml) was added
  3. washthe solution washed with diethyl ether (2×50 ml)
  4. filtrationThe precipitate was filtered
  5. washwashed with diethyl ether
  6. customrecrystallized

Sources & evidence

ORD record
ord-fbcaa23dae8b4abbbfc09e010761b08d
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

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