Toluene → HCID 66777815, compound

HRID 406313Notes

Reaction equation

HRID 406313 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:29]=[C:12]3[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])(O)[CH2:14][CH2:15][CH2:16][CH2:17][N:11]3[N:10]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:29]=[C:12]3[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:27])([F:26])[F:28])=[CH:14][CH2:15][CH2:16][CH2:17][N:11]3[N:10]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 66618788HCID 66618788, compound

Product 1

HCID 66777815HCID 66777815, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-9-(2-trifluoromethylphenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-9-ol obtained in Example 181 (49 mg), p-toluenesulfonic acid (76 mg) and toluene (7 mL) was heated under reflux for two hours. Ethyl acetate and saturated sodium bicarbonate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The solid was removed by filtration. The mother liquor was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (chloroform-methanol system) to obtain 3.46 mg of the title compound as an oil. The property values of the compound are as follows.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe solid was removed by filtration
  7. concentrationThe mother liquor was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform-methanol system)

Sources & evidence

ORD record
ord-27ba5663fa5540e58449c25d1b6a2579
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…