Trifluoromethanesulfonic acid → 8-Isopropyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic Acid Ethyl Ester

HRID 351839Notes

Reaction equation

HRID 351839 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][N:13](CC1C=CC(OC)=CC=1OC)[C:12](=[O:27])[C:11]1[CH:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[CH:30]=[CH:31][C:10]2=1)=[O:5])[CH3:2].FC(F)(F)S(O)(=O)=O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][NH:13][C:12](=[O:27])[C:11]1[CH:28]=[C:29]([CH:32]([CH3:33])[CH3:34])[CH:30]=[CH:31][C:10]2=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 699231145-(2,4-Dimethoxy-benzyl)-8-isopropyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic Acid Ethyl Ester

Product 1

HCID 699215768-Isopropyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-(2,4-Dimethoxy-benzyl)-8-isopropyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester (410 mg, 0.9 mmol) was suspended in CH2Cl2 (3.0 mL), cooled in ice, and diluted slowly with trifluoroacetic acid (2.0 mL). The resulting solution was treated at 5° C. with trifluoromethanesulfonic acid (1.0 mL, 1.3 mmol). The red solution was stirred at room temperature for 2 h. The mixture was then evaporated and dissolved in CH2Cl2 (20 mL), washed with sodium hydrogen carbonate (10%, 2×5 mL) and the organic layer was dried (Na2SO4) and evaporated. Trituration with EtOAc. Yield: 250 mg (90%). m/z 313 (MH).

Workup

  1. temperaturecooled in ice
  2. customThe mixture was then evaporated
  3. dissolutiondissolved in CH2Cl2 (20 mL)
  4. washwashed with sodium hydrogen carbonate (10%, 2×5 mL)
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6c820a6355104183b83d2eb490d9a0d3
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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