Trifluoroacetic acid → Quinoline-6-carboxylic acid (5-(3-hydroxy-phenoxy)-thiophen-2-ylmethyl)-amide

HRID 2080247

Reaction equation

HRID 2080247 reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:17]=[C:18]([CH:39]=[CH:40][CH:41]=1)[O:19][C:20]1[S:24][C:23]([CH2:25][NH:26][C:27]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][CH:33]=[CH:32]3)=[O:28])=[CH:22][CH:21]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(SC)C=CC=CC=1>[OH:15][C:16]1[CH:17]=[C:18]([CH:39]=[CH:40][CH:41]=1)[O:19][C:20]1[S:24][C:23]([CH2:25][NH:26][C:27]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][CH:33]=[CH:32]3)=[O:28])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67119634Quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophen-2-ylmethyl)-amide

Product 1

HCID 58387979Quinoline-6-carboxylic acid (5-(3-hydroxy-phenoxy)-thiophen-2-ylmethyl)-amideYield 80%

Reagents, catalysts & solvents 1

HCID 7520ThioanisoleSolvent

Procedure

Trifluoroacetic acid (1.0 mL) and thioanisole (100 μl) were added to the resulting quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophene-2-ylmethyl)-amide (73 mg, 0.156 mmol), and the solution was stirred for 30 minutes at room temperature. The reaction solution was neutralized with an aqueous solution of saturated sodium bicarbonate, then, extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (ethyl acetate: methanol), and the title compound (47 mg, 80%) was obtained as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by NH silica gel column chromatography (ethyl acetate: methanol)

Sources & evidence

ORD record
ord-e005000e92794df68982b8121a740061
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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