Isopropanol → HCID 22032046, compound

HRID 1792467Notes

Reaction equation

HRID 1792467 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[O:12][C:13](S(C)=O)=[N:14][N:15]=3)=[CH:9][N:10]=2)[CH:7]=1.BrC1C=CC2N(C(C3OC(S(C)(=O)=O)=NN=3)=CN=2)C=1.[CH:38]([OH:41])([CH3:40])[CH3:39].[Cl-].[NH4+]>O.C(OCC)(=O)C.O1CCCC1.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[O:12][C:13]([O:41][CH:38]([CH3:40])[CH3:39])=[N:14][N:15]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

9

Reactant 4

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 22031295HCID 22031295, compoundHCID 22032228HCID 22032228, compound

Product 1

HCID 22032046HCID 22032046, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture consisting of 60 mg crude product of a mixture of 6-bromo-3-(5-methanesulfinyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine and 6-bromo-3-(5-methylsulfonyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine obtained in the synthesis process in Production Example 280, 2 mL isopropyl alcohol, 0.3 mL triethylamine and 3 mL anhydrous tetrahydrofuran was heated overnight under reflux. An aqueous saturated ammonium chloride solution, ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 33 mg of the title compound as a white solid.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. customthe filtrate was evaporated
  8. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2c35e213c542401e8ac9e4c82950976c
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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