Trifluoromethanesulfonic acid → HCID 22713540, compound

HRID 351845Notes

Reaction equation

HRID 351845 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][N:12]4[C:18]=3[CH2:17][N:16](CC3C=CC(OC)=CC=3OC)[C:15](=[O:30])[C:14]3[CH:31]=[C:32]([CH3:35])[CH:33]=[CH:34][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][N:12]4[C:18]=3[CH2:17][NH:16][C:15](=[O:30])[C:14]3[CH:31]=[C:32]([CH3:35])[CH:33]=[CH:34][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 22713528HCID 22713528, compound

Product 1

HCID 22713540HCID 22713540, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-5-(2,4-dimethoxy-benzyl)-8-methyl-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one (17.5 g, 37.1 mmol) was suspended in CH2Cl2 (100 mL), cooled in ice, and diluted slowly with trifluoroacetic acid (85.2 mL). The resulting solution was treated at 5° C. with trifluoromethanesulfonic acid (4.9 mL, 55.7 mmol). The red solution was stirred at room temperature for 4 h. The mixture was then evaporated and dissolved in CH2Cl2 (100 mL), washed with sodium hydrogen carbonate (10%, 2×50 mL) and the organic layer was dried (Na2SO4) and evaporated. Digestion in EtOAc (100 mL) followed by the slow addition of hexane (100 mL). The solid obtained was washed twice with EtOAc: Hexane (1:1, 2×20 mL). Yield: 9.3 g (78%) m/z 321 (M).

Workup

  1. temperaturecooled in ice
  2. customThe mixture was then evaporated
  3. dissolutiondissolved in CH2Cl2 (100 mL)
  4. washwashed with sodium hydrogen carbonate (10%, 2×50 mL)
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. customevaporated
  7. additionDigestion in EtOAc (100 mL) followed by the slow addition of hexane (100 mL)
  8. customThe solid obtained
  9. washwas washed twice with EtOAc: Hexane (1:1, 2×20 mL)

Sources & evidence

ORD record
ord-da0bed59abeb491a9689df7e49ae1961
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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