Hydrochloric Acid → 8-Amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile

HRID 420514Notes

Reaction equation

HRID 420514 reaction equation
[N:1]([C:4]1[C:5]2[N:6]([CH:20]=[CH:21][N:22]=2)[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:9]=1[C:10]#[N:11])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CO.O>[NH2:1][C:4]1[C:5]2[N:6]([CH:20]=[CH:21][N:22]=2)[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:9]=1[C:10]#[N:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 86634890HCID 86634890, compound

Product 1

HCID 666590048-Amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrileYield 52.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of crude 8-azido-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (68 mg, 0.21 mmol) and triphenylphosphine (83.7 mg, 0.32 mmol) in MeOH (2.5 mL) was stirred and refluxed for 1 h. 2 M HCl in water (1 mL) was added and the reaction mixture was further refluxed for 1 h. The reaction mixture was cooled to RT, concentrated under vacuum and the remaining residue was dissolved in water. The aqueous solution was basified to pH 12 by the addition of 2 M NaOH in water. The resulting slurry was extracted with DCM (2×) and the combined organic fractions were dried over Na2SO4, filtered and evaporated. The remaining residue was dissolved in hot MeOH, then the solution was slowly cooled to RT and the formed precipitate was filtered and washed with cold MeOH to yield the title compound (32.5 mg, 0.11 mmol, 52%) as a brownish solid. MS: 303 [M+1]+; HPLC: AtRet=1.72.

Workup

  1. temperaturerefluxed for 1 h
  2. temperaturethe reaction mixture was further refluxed for 1 h
  3. concentrationconcentrated under vacuum
  4. dissolutionthe remaining residue was dissolved in water
  5. additionThe aqueous solution was basified to pH 12 by the addition of 2 M NaOH in water
  6. extractionThe resulting slurry was extracted with DCM (2×)
  7. dry with materialthe combined organic fractions were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe remaining residue was dissolved in hot MeOH
  11. temperaturethe solution was slowly cooled to RT
  12. filtrationthe formed precipitate was filtered
  13. washwashed with cold MeOH

Sources & evidence

ORD record
ord-a566f4a363b14e3380de5074e877e9b5
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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