Trifluoroacetic acid → 3-(6-(Sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoic acid

HRID 1854766Notes

Reaction equation

HRID 1854766 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]([C:12]1[N:17]=[C:16]2[O:18][C:19]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[C:20]([C:21](=[O:24])[NH:22][CH3:23])[C:15]2=[CH:14][C:13]=1[C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[C:35]([O:37]C(C)(C)C)=[O:36])([CH2:10][CH3:11])[CH3:9]>C(Cl)Cl>[CH:8]([C:12]1[N:17]=[C:16]2[O:18][C:19]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[C:20]([C:21](=[O:24])[NH:22][CH3:23])[C:15]2=[CH:14][C:13]=1[C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[C:35]([OH:37])=[O:36])([CH2:10][CH3:11])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90402567Tert-butyl 3-(6-(sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate

Product 1

HCID 904024833-(6-(Sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.90 ml, 12 mmol) was added to a stirring solution of tert-butyl 3-(6-(sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate (118 mg, 0.235 mmol) in DCM (2.3 ml) at rt. The reaction was allowed to stir for 2 h and then was concentrated to dryness azeotroping with toluene 2×. The resulting solid was triturated with DCM to give 3-(6-(sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoic acid (98 mg, 0.22 mmol, 93% yield) consistent by LCMS. LC-MS retention time: 1.84 min; m/z (MH+): 447. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. concentrationwas concentrated to dryness
  2. customazeotroping with toluene 2×
  3. customThe resulting solid was triturated with DCM

Sources & evidence

ORD record
ord-b33e4aa27be040d6b7291ef2386b7e01
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

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