Trifluoroacetic acid → HCID 70664968, compound

HRID 1403397Notes

Reaction equation

HRID 1403397 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]([O:27]CC5C=CC(OC)=CC=5)=[O:26])[CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[CH:3]=[N:2]1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]([OH:27])=[O:26])[CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70665058HCID 70665058, compound

Product 1

HCID 70664968HCID 70664968, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-methoxyphenyl)methyl 2-(1,2-benzoxazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (50 mg, 0.10 mmol) in dichloromethane (10 mL) was added 2,2,2-trifluoroacetic acid (1 mL). The solution was stirred for 30 min at room temperature. Then the reaction was quenched by the addition of water (100 mL), extracted with dichloromethane (3×30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 5% dichloromethane in methanol to afford 2-(1,2-benzoxazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid as a yellow solid (12.3 mg, 33%).

Workup

  1. customThen the reaction was quenched by the addition of water (100 mL)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography
  7. washeluting with 5% dichloromethane in methanol

Sources & evidence

ORD record
ord-b2b01249428343279d6a65c7ca653a78
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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