Acetyl chloride → HCID 178419073, compound

HRID 860135Notes

Reaction equation

HRID 860135 reaction equation
C[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=O.[CH:16]1([N+:22]#[C-:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl:24](O)(=O)(=O)=O.[C:29]([Cl:32])(=[O:31])[CH3:30]>CO.C(Cl)Cl.O>[ClH:24].[Cl-:32].[C:29]([N+:8]1[C:14]([C:10]2[O:9][CH:13]=[CH:12][CH:11]=2)=[C:23]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=12)(=[O:31])[CH3:30]

Participants

9

Reactant 5

HCID 6367Acetyl chlorideHCID 7362FurfuralHCID 153482-Amino-5-methylpyridineHCID 24247Perchloric AcidHCID 79129Cyclohexyl isocyanide

Product 1

HCID 178419073HCID 178419073, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

655 mg (6.1 mmol) 5-methyl-2-aminopyridin were placed in 12 ml methanol, and 874 mg (0.75 ml; 9.1 mmol) furan-2-carbaldehyde, 768 mg (0.86 ml; 7.0 mmol) cyclohexylisonitrile and 0.59 ml aqueous perchloric acid (20 m %) were then added and stirred at ambient temperature for 22 hours. 50 ml water and 40 ml DCM were added for processing purposes, stirred for 10 minutes, and the phases then separated. The aqueous phase was additionally extracted three times with 20 ml DCM in each case and the combined organic phases then shaken briefly with 50 ml saturated sodium chloride solution, separated off, dried over magnesium sulfate, filtered and concentrated under vacuum. The intermediate product obtained (1.83 g; 6.2 mmol) was dissolved in 10 ml DCM, and four equivalents acetyl chloride (24.8 mmol; 1.8 ml) were added dropwise while stirring at 20° C. and were stirred for a further four hours. The reaction mixture was then concentrated under vacuum and dried in an oil pump vacuum. The untreated product (about 2 g) was dissolved in 15.5 ml 2-butanone, 51 μl water and 0.72 ml trimethylchlorosilane were added and the mixture was stirred overnight. The precipitated HCl adduct of 1-acetyl-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyridin-1-ium chloride was suction-filtered and dried under vacuum. 776 mg 1-acetyl-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyridin-1-ium chloride hydrochloride were obtained.

Workup

  1. stirringstirred for 10 minutes
  2. customthe phases then separated
  3. extractionThe aqueous phase was additionally extracted three times with 20 ml DCM in each case
  4. stirringthe combined organic phases then shaken briefly with 50 ml saturated sodium chloride solution
  5. customseparated off
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe intermediate product obtained (1.83 g; 6.2 mmol)
  10. stirringwhile stirring at 20° C.
  11. stirringwere stirred for a further four hours
  12. concentrationThe reaction mixture was then concentrated under vacuum
  13. customdried in an oil pump vacuum
  14. dissolutionThe untreated product (about 2 g) was dissolved in 15.5 ml 2-butanone
  15. addition51 μl water and 0.72 ml trimethylchlorosilane were added
  16. stirringthe mixture was stirred overnight
  17. filtrationThe precipitated HCl adduct of 1-acetyl-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyridin-1-ium chloride was suction-filtered
  18. customdried under vacuum

Sources & evidence

ORD record
ord-03955e1ce650411e87c5d6c12d1d10b4
Source dataset
uspto-grants-2006_12
Patent number
US07153873B2

Reaction notes

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