2-cyclohexylaniline

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

Procedure: The carbamate obtained as above was treated with 4 M HCl in dioxane following the procedure described in Example 80 to afford 2-cyclohexylphenylamine as a hydrochloride salt.

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

Procedure: The carbamate obtained as above was treated with 4 M HCl in dioxane following the procedure described in Example 80 to afford 2-cyclohexylphenylamine as a hydrochloride salt.

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

Procedure: 3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (2.0 g) and 1,1'-carbonyldiimidazole (2.0 g) were mixed in THF (20mL, anhydrous) and stirred for 1 h. 2-Cyclohexylaniline (2.2 g) was added, and the contents were heated at reflux for 2 h. After cooling to RT, the contents were concentrated in vacuo leaving a foam (3.7 g). The foam was chromatographed on silica gel (Waters Prep 500) eluting with EtOAc and hexanes to give the desired amide as a white foam (750 mg). The foam was crystallized from EtOAc /pentane to give the product as a white solid (510 mg). the contents were heated at reflux for 2 h the contents were concentrated in vacuo

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

Procedure: To 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid chloride (1.6 g) in CH2Cl12 (25 mL) at 0° C. was added dropwise a solution of 2-cyclohexylaniline (1.3 g) and triethylamine (1.0 mL) in CH2Cl2 (25 mL). The contents were stirred overnight, coming to RT. The contents were washed with water, 2N HCl (2×100 mL), dried (MgSO4) and concentrated in vacuo leaving an amber foam (2.9 g). Crystallization from EtOAc/hexane gave the desired amide as white crystals (1.2 g). Most of the compounds of the present invention were made via this coupling procedure. coming to RT The contents were washed with water, 2N HCl (2×100 mL) dried (MgSO4) concentrated in vacuo

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

Procedure: To a mixture of 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid (0.08 g), 2-cyclohexylaniline (0.06 g), and 2 ml of N,N-dimethylformamide, 1-hyhdroxy benzotriazol (0.05 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.07 g) were added, and stirred at room temperature over 2 hours. The reactant was poured into 20 ml of water, and extracted with 80 ml of ethyl acetate. The extract was washed saturated saline solution, dried with magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate:toluene=1:1), and recrystallized with ethyl acetate to yield N-2-cyclohexylphenyl-3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-amide (0.08 g, 64%) as a yellow needle crystal. mp: 160.2-161.4° C. were added extracted with 80 ml of ethyl acetate The extract was washed saturated saline solution dried with magnesium sulfate concentrated in vacuo The resulting residue was purified by silica gel column chromatography (ethyl acetate:toluene=1:1) recrystallized with ethyl acetate

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

Procedure: The carbamate obtained as above was treated with 4 M HCl in dioxane following the procedure described in Example 80 to afford 2-cyclohexylphenylamine as a hydrochloride salt.

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

Procedure: The carbamate obtained as above was treated with 4 M HCl in dioxane following the procedure described in Example 80 to afford 2-cyclohexylphenylamine as a hydrochloride salt.