p-Toluenesulfonic acid → 1-{12-Fluoro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-one

HRID 1530702Notes

Reaction equation

HRID 1530702 reaction equation
C([O:3][C:4]([C:6]1[CH:19]=[C:18]2[C:9]([O:10][CH2:11][CH2:12][N:13]3[C:17]2=[N:16][C:15]([C:20]2[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[C:22]([CH3:28])[N:21]=2)=[CH:14]3)=[CH:8][C:7]=1[F:29])=[CH2:5])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[F:29][C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][C:6]=1[C:4](=[O:3])[CH3:5])[C:17]1[N:13]([CH:14]=[C:15]([C:20]3[N:24]([CH:25]([CH3:26])[CH3:27])[N:23]=[C:22]([CH3:28])[N:21]=3)[N:16]=1)[CH2:12][CH2:11][O:10]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 6831301413-(1-Ethoxyethenyl)-12-fluoro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene

Product 1

HCID 683130591-{12-Fluoro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-oneYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above crude 13-(1-ethoxyethenyl)-12-fluoro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (1.97 g, 4.93 mmol) and p-toluenesulfonic acid (90 mg, 0.50 mmol) in acetone (10.0 ml) was heated under reflux for 30 min. Evaporation under reduced pressure gave a yellow solid, which was purified using flash chromatography on silica gel using 4% dichloromethane in methanol as eluant to afford the title compound (1.55 g, 85% yield for two steps). LCMS m/z [M+H]+ 370.1

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. customEvaporation under reduced pressure
  4. customgave a yellow solid, which
  5. customwas purified

Sources & evidence

ORD record
ord-e04fb74137dd4793aeafddf2bdbf7bfa
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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