Dimethylformamide → HCID 86628519, compound

HRID 546785Notes

Reaction equation

HRID 546785 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])(=O)=O.[CH3:20][C:21]1[N:22]=[CH:23][N:24]([C:26]2[C:27](O)=[N:28][C:29](/[CH:32]=[CH:33]/[C:34]3[N:52]=[C:37]4[C@H:38]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=5[C:48]([F:51])([F:50])[F:49])[CH2:39][CH2:40][CH2:41][N:36]4[N:35]=3)=[CH:30][CH:31]=2)[CH:25]=1.CN(C=O)C>C(OCC)(=O)C.O>[CH3:20][C:21]1[N:22]=[CH:23][N:24]([C:26]2[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]3[N:52]=[C:37]4[CH:38]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=5[C:48]([F:50])([F:51])[F:49])[CH2:39][CH2:40][CH2:41][N:36]4[N:35]=3)=[N:28][C:27]=2[O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178429903HCID 178429903, compound

Product 1

HCID 86628519HCID 86628519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (83.7 mg) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (35.7 μL) were added to a mixture of 3-(4-methyl-1H-imidazol-1-yl)-6-{(E)-2-[8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]vinyl}pyridin-2-ol synthesized in Example 344 (100 mg) and DMF (1.2 mL), and the reaction solution was stirred at room temperature for four hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=4:1→ethyl acetate) to obtain a racemate of the title compound (110 mg). The resulting racemate (110 mg) was separated by CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm, mobile phase: hexane:ethanol=5:5, flow rate: 11 mL/min) to obtain the title optically active compound with a retention time of 13 minutes and positive optical rotation (51 mg) and the title optically active compound with a retention time of 18 minutes and negative optical rotation (53 mg).

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=4:1→ethyl acetate)

Sources & evidence

ORD record
ord-a88b42d0256540a78379c8cf88c1e635
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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