HCID 25053577, compound → HCID 178520481, compound

HRID 1914780Notes

Reaction equation

HRID 1914780 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13](=[O:25])/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[N:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[N+:22]([C:19]1[CH:18]=[CH:17][C:16](/[CH:15]=[CH:14]/[C:13]([C:11]2[N:10]=[N:9][NH:8][CH:12]=2)=[O:25])=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

3

Reactant 1

HCID 25053577HCID 25053577, compound

Product 1

HCID 178520481HCID 178520481, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

To a 5 mL round-bottom flask equipped with a magnetic stir bar, was added enone 4n (27 μmol) in TFA (1 mL). The mixture was stirred 7 hours at 65° C. Then, the TFA was removed under reduced pressure and the crude was purified by chromatography (100% AcOEt) to give the pure product, as a white solid in 45% isolated. m.p. 1H NMR (300 MHz, d6-DMSO) δ 8.83 (s, 1H), 8.34 (d, 2H, J=8.9 Hz), 8.17 (d, 2H, J=8.8 Hz), 8.05 (d, 1H, J=16.1 Hz), 7.97 (d, 1H, J=15.9 Hz). 13C NMR (75 MHz, CDCl3) δ. HRMS (FAB) calcd for C18H15N4O3 ([M+H]+). found.

Workup

  1. customTo a 5 mL round-bottom flask equipped with a magnetic stir bar
  2. customThen, the TFA was removed under reduced pressure
  3. customthe crude was purified by chromatography (100% AcOEt)
  4. customto give the pure product
  5. customas a white solid in 45% isolated

Sources & evidence

ORD record
ord-ac2e29d215804d26a9424572b34721fa
Source dataset
uspto-grants-2013_12
Patent number
US08614233B2

Reaction notes

Loading…