isocyanocyclohexane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.59 gm of 4-(p-aminophenyl)-1-H-imidazole, 1.2 gm of cyclohexyl isonitrile, and 0.99 gm of CuCl was heated at 150° C. for three hours. The thick reaction mixture was extracted with methanol. The methanol solution, after treatment with charcoal, was evaporated to dryness and extracted with ethyl acetate and 10% hydrochloric acid. The acid solution was adjusted to pH 7.5 with 17% Na2CO3 and extracted with ethyl acetate. The organic solution was evaporated to dryness. The substance remaining after recrystallization from acetone comprised 0.25 gm of the desired product. The thick reaction mixture was extracted with methanol The methanol solution, after treatment with charcoal, was evaporated to dryness extracted with ethyl acetate and 10% hydrochloric acid extracted with ethyl acetate The organic solution was evaporated to dryness after recrystallization from acetone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bzl-NH2 288 μl (2.64 mmol) and benzyl phenethylketone 592 mg (2.64 mmol) were dissolved in MeOH (5 ml) at rt and the solution was stirred overnight. To the mixture were added formic acid 99.6 μl (2.64 mmol) and cyclohexylisocyanide 298 μl (2.4 mmol) at rt, which was allowed to react at rt for 2 weeks. Insoluble material in MeOH was collected by filtration and washed with MeOH, ether and then n-hexane. The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane. Yield 540 mg (48.2%), NMR in CDCl3 ; δ=0.8-1.8 cyclohexyl (11H), δ=2.1-4.75 CH2 (8H), δ=5.45-5.55 NH (1H), δ=7.0-7.4 phenyl (15H), δ=8.25 (main) and 8.4 (minor) formyl (1H). to react at rt for 2 weeks Insoluble material in MeOH was collected by filtration washed with MeOH, ether The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bzl-NH2 288 μl (2.64 mmol) and benzyl phenethylketone 592 mg (2.64 mmol) were dissolved in MeOH (5 ml) at rt and the solution was stirred overnight. To the mixture were added formic acid 99.6 μl (2.64 mmol) and cyclohexylisocyanide 298 μl (2.4 mmol) at rt, which was allowed to react at rt for 2 weeks. Insoluble material in MeOH was collected by filtration and washed with MeOH, ether and then n-hexane. The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane. Yield 540 mg (48.2%), NMR in CDCl3 ; δ=0.8-1.8 cyclohexyl (11H), δ=2.1-4.75 CH2 (8H), δ=5.45-5.55 NH (1H), δ=7.0-7.4 phenyl (15H), δ=8.25 (main) and 8.4 (minor) formyl (1H). to react at rt for 2 weeks Insoluble material in MeOH was collected by filtration washed with MeOH, ether The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bzl-NH2 288 μl (2.64 mmol) and benzyl phenethylketone 592 mg (2.64 mmol) were dissolved in MeOH (5 ml) at rt and the solution was stirred overnight. To the mixture were added formic acid 99.6 μl (2.64 mmol) and cyclohexylisocyanide 298 μl (2.4 mmol) at rt, which was allowed to react at rt for 2 weeks. Insoluble material in MeOH was collected by filtration and washed with MeOH, ether and then n-hexane. The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane. Yield 540 mg (48.2%), NMR in CDCl3 ; δ=0.8-1.8 cyclohexyl (11H), δ=2.1-4.75 CH2 (8H), δ=5.45-5.55 NH (1H), δ=7.0-7.4 phenyl (15H), δ=8.25 (main) and 8.4 (minor) formyl (1H). to react at rt for 2 weeks Insoluble material in MeOH was collected by filtration washed with MeOH, ether The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound (27) was prepared in accordance with general instructions 1 from 1.0 ml 2-aminopyridine solution (0.1 M, MC), 0.575 ml cyclohexyl isocyanide solution (0.2 M, MC), 0.500 ml 3-bromothiophene-2-carbaldehyde solution (0.3 M, MC), and 10 μl perchloric acid (w=20%). Calculated mass 376.3; found mass 376.4/378.3 (ESI-MS)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. stirred for 10 minutes the phases then separated The aqueous phase was additionally extracted three times with 20 ml DCM in each case the combined organic phases then shaken briefly with 50 ml saturated sodium chloride solution separated off dried over magnesium sulfate filtered concentrated under vacuum The intermediate product obtained (1.83 g; 6.2 mmol) while stirring at 20° C. were stirred for a further four hours The reaction mixture was then concentrated under vacuum 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 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 dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 26 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) thiophene-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in process step c) and d) by reacting the resultant reaction product with 0.4 mmol acetylchloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 26 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) thiophene-2-carbaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in process step c) and d) by reacting the resultant reaction product with 0.4 mmol acetylchloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 25 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in process step c) and d) by reacting the resultant reaction product with 0.4 mmol acetylchloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 24 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in process step c) and d) by reacting the resultant reaction product with 0.4 mmol acetylchloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 24 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2-amino-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) cyclohexylisonitrile solution (0.2 M, DCM), 0.500 ml (0.15 mmol) acetaldehyde solution (0.3 M, DCM) and 10 μl perchloric acid (w=20%) and in process step c) and d) by reacting the resultant reaction product with 0.4 mmol acetylchloride.