Hydrochloric Acid → HCID 24821794, compound

HRID 2059512Notes

Reaction equation

HRID 2059512 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([O:20]COC)=[CH:16][N:15]3[CH:24]=2)=[CH:8][CH:7]=1.Cl.O>C(O)(C)C>[F:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][N:15]3[CH:24]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68587943HCID 68587943, compound

Product 1

HCID 24821794HCID 24821794, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.18 g (corresponding to 3.57 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-methoxymethoxyimidazo[1,2-a]pyridine was dissolved in 29 mL of isopropyl alcohol, and 0.59 mL of conc. hydrochloric acid was added thereto. Then, the mixture was refluxed for 23 hours. After the reaction solution was cooled, the solution was poured into water, and extracted twice by a salting-out extraction procedure using chloroform with addition of sodium chloride. The combined chloroform layer was dried over anhydrous magnesium sulfate. The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=10/1), to obtain 481 mg (corresponding to 1.68 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-hydroxyimidazo[1,2-a]pyridine (hereinafter referred to as Compound 2) (FIG. 3, Step 10).

Workup

  1. temperatureThen, the mixture was refluxed for 23 hours
  2. temperatureAfter the reaction solution was cooled
  3. extractionextracted twice by a salting-out extraction procedure
  4. additionwith addition of sodium chloride
  5. dry with materialThe combined chloroform layer was dried over anhydrous magnesium sulfate
  6. customThe resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-b5a44cd795b54272b4de73317c71bf2c
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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