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

HRID 351843Notes

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]([O:35][CH3:36])[CH:33]=[CH:34][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[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]([O:35][CH3:36])[CH:33]=[CH:34][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-5-(2,4-dimethoxy-benzyl)-8-methoxy-4,5-dihydro-2,5,10b-triaza-benzo[e]azulen-6-one (5 g, 10.3 mmol) were dissolved in CH2Cl2 (30 mL), cooled to 0° C., then TFA (30 mL) was added, followed by trifluoromethanesulfonic acid (2 mL, 22.9 mmol). The mixture was stirred for 4 h at rt, evaporated, the residue dissolved in CH2Cl2 (100 mL), and extracted with 10% NaHCO3. The product precipitated upon evaporation of CH2Cl2. Yield: 3 g (86%); mp 245° C. m/z 337 (M).

Workup

customevaporated
dissolutionthe residue dissolved in CH2Cl2 (100 mL)
extractionextracted with 10% NaHCO3
customThe product precipitated upon evaporation of CH2Cl2

Sources & evidence

ORD record: ord-4e7eb174752d4994a12f70aeb8fdcc60
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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