Trifluoroacetic acid → HCID 86671041, compound

HRID 1037315Notes

Reaction equation

HRID 1037315 reaction equation
[I:1][C:2]1[C:3](=[O:30])[C:4]2[CH:5]=[CH:6][N:7]3[C:20](=[O:21])[N:19](COCC[Si](C)(C)C)[N:18]=[C:8]3[C:9]=2[O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:1][C:2]1[C:3](=[O:30])[C:4]2[CH:5]=[CH:6][N:7]3[C:20](=[O:21])[NH:19][N:18]=[C:8]3[C:9]=2[O:10][C:11]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86671039HCID 86671039, compound

Product 1

HCID 86671041HCID 86671041, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred ice-cooled solution of 7-iodo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione (60 mg, 0.112 mmol) in DCM (2 mL) was added TFA (2 mL). The reaction mixture was allowed to warm to RT. After 16 hours, the solvents were removed in vacuo, the residue was dissolved in THF (2 mL) and benzyltrimethylammonium hydroxide (40% in MeOH, 0.05 mL) was added. The reaction mixture was stirred at RT for 1 hour. EtOAc was added and the mixture was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound (50.4 mg) as a buff solid. LCMS (Method B): RT=3.84 min, [M+H]+=406.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in THF (2 mL)
  3. additionbenzyltrimethylammonium hydroxide (40% in MeOH, 0.05 mL) was added
  4. additionEtOAc was added
  5. washthe mixture was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f383b4013f94dc3b42116f1abafd26b
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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