Trifluoromethanesulfonic acid → 3(-3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-bromo-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one

HRID 351846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351846
[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]([Br: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]([Br:35])[CH:33]=[CH:34][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 62406Trifluoromethanesulfonic acidHCID 227134723-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-5-(2,4-dimethoxy-benzyl)-8-bromo-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one

Produkt 1

HCID 227134693(-3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-bromo-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

3-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-5-(2,4-dimethoxy-benzyl)-8-bromo-4,5-dihydro-2,5,10b-triaza-benzo[e]azulene-6-one (1.1 g, 2.0 mmol) was suspended in CH2Cl2 (6 mL), cooled in ice, and diluted slowly with trifluroacetic acid (4.7 mL). The resulting solution was treated at 5° C. with trifluoromethanesulfonic acid (266 μL, 3.0 mmol). The red solution was stirred at room temperature for 1.5 h. The mixture was then evaporated and dissolved in CH2Cl2 (10 mL), washed with sodium hydrogen carbonate (sat., 10 mL) and the organic layer was dried (Na2SO4) and evaporated. Trituration with EtOAc. Yield: 772 mg (100%). m/z 385/387 (M—H−).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fc0912a859c14ffdae472976cf26dac1
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743789B2

Notizen zur Reaktion

Wird geladen…