반응 #7630

반응 방정식

5-methyl-2-aminopyridin

acetyl chloride

furan-2-carbaldehyde

cyclohexylisonitrile

perchloric acid

→

1-acetyl-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyridin-1-ium chloride hydrochloride

용매

DCM

water

methanol

DCM

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 10 minutes
2. 2
   기타the phases then separated
3. 3
   추출The aqueous phase was additionally extracted three times with 20 ml DCM in each case
4. 4
   workup.STIRRINGthe combined organic phases then shaken briefly with 50 ml saturated sodium chloride solution
5. 5
   기타separated off
6. 6
   건조dried over magnesium sulphate
7. 7
   여과filtered
8. 8
   농축concentrated under vacuum
9. 9
   기타The intermediate product obtained (1.83 g; 6.2 mmol)
10. 10
    workup.STIRRINGwhile stirring at 20° C.
11. 11
    workup.STIRRINGwere stirred for a further four hours
12. 12
    농축The reaction mixture was then concentrated under vacuum
13. 13
    기타dried in an oil pump vacuum
14. 14
    workup.DISSOLUTIONThe untreated product (about 2 g) was dissolved in 15.5 ml 2-butanone
15. 15
    workup.ADDITION51 μl water and 0.72 ml trimethylchlorosilane were added
16. 16
    workup.STIRRINGthe mixture was stirred overnight
17. 17
    여과The precipitated HCl adduct of 1-acetyl-3-cyclohexylamino-2-furan-2-yl-imidazo[1,2-a]pyridin-1-ium chloride was suction-filtered
18. 18
    기타dried under vacuum

실험 절차

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 sulphate, 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.

출처