Methanesulfonic Acid → HCID 86615145, compound

HRID 599623Notes

Reaction equation

HRID 599623 reaction equation
CS(O)(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2(O)[CH2:18][CH2:17][CH2:16][N:15]3[N:19]=[C:20](/[CH:22]=[CH:23]/[C:24]4[CH:29]=[CH:28][C:27]([N:30]5[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]5)=[C:26]([O:36][CH3:37])[CH:25]=4)[N:21]=[C:14]23)=[CH:9][CH:8]=1.[N-:39]=[N+:40]=[N-:41].[Na+].O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[N:39]([C:13]1([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)[CH2:18][CH2:17][CH2:16][N:15]2[N:19]=[C:20](/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]4)=[C:26]([O:36][CH3:37])[CH:25]=3)[N:21]=[C:14]12)=[N+:40]=[N-:41]

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 33557Sodium AzideHCID 67067262HCID 67067262, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 86615145HCID 86615145, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid (0.3 mL) was added to a solution of 8-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-8-ol synthesized by the method in Examples 70 and 71 (45 mg) and sodium azide (66 mg) in TFA (1 mL), and the reaction solution was stirred at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate. The solution was added to saturated sodium bicarbonate water, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate) to obtain 28 mg of the title compound. The property values of the compound are as follows.

Workup

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

Sources & evidence

ORD record
ord-5b4a8c08c56041eb80d8d8be2bd5be65
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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