65732-69-6

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

Procedure: In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (S)-pyrrolidine-2-carbonitrile hydrochloride and isolated as light-yellow solid (11.5 mg, 65%). MS (m/e): 396.4 (MH+).

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

Procedure: To a solution of (1R,3S,4S,6R)-2-(tert-butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid obtained in Example 5-6 (90 mg) in N,N-dimethylformamide (1.6 mL), was added (2S)-2-pyrrolidinecarbonitrile hydrochloride (55.7 mg) 1-hydroxy-7-azabenzotriazole (57.2 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (65 mg). The mixture was then stirred at room temperature for 6 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (85.4 mg) as a solid. The resulting mixture was evaporated in vacuo the residue was chromatographed on silica gel eluting with ethyl acetate

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

Procedure: To a solution of (1R,3S,4S,6R)-2-(tert-butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid obtained in Example 5-6 (90 mg) in N,N-dimethylformamide (1.6 mL), was added (2S)-2-pyrrolidinecarbonitrile hydrochloride (55.7 mg) 1-hydroxy-7-azabenzotriazole (57.2 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (65 mg). The mixture was then stirred at room temperature for 6 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (85.4 mg) as a solid. The resulting mixture was evaporated in vacuo the residue was chromatographed on silica gel eluting with ethyl acetate

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

Procedure: To a solution of (1S,3S,4S,5S,6R)-2-(tert-butoxycarbonyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid obtained in Example 1-3 (500 mg) 1-hydroxybenzotriazole hydrate (415 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (493 mg) in dimethylformamide (10 mL), were added diisopropylethylamine and (2S)-2-pyrrolidinecarbonitrile hydrochloride with cooling on an ice bath. The reaction mixture was stirred at that temperature for 3 hrs. with cooling on an ice bath

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

Procedure: To a solution of (1S,3S,4S,5S,6R)-2-(tert-butoxycarbonyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid obtained in Example 1-3 (500 mg) 1-hydroxybenzotriazole hydrate (415 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (493 mg) in dimethylformamide (10 mL), were added diisopropylethylamine and (2S)-2-pyrrolidinecarbonitrile hydrochloride with cooling on an ice bath. The reaction mixture was stirred at that temperature for 3 hrs. with cooling on an ice bath

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

Procedure: In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (S)-pyrrolidine-2-carbonitrile hydrochloride and isolated as light-yellow solid (11.5 mg, 65%). MS (m/e): 396.4 (MH+).

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

Procedure: In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (S)-pyrrolidine-2-carbonitrile hydrochloride and isolated as light-yellow solid (11.5 mg, 65%). MS (m/e): 396.4 (MH+).

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

Procedure: In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (S)-pyrrolidine-2-carbonitrile hydrochloride and isolated as light-yellow solid (11.5 mg, 65%). MS(m/e): 396.4 (MH+).

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

Procedure: Starting from (S)-N5-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-ornithine, cyclohexanesulphonyl chloride and (S)-2-cyano-pyrrolidine hydrochloride, the expected product is obtained according to the procedure described in Example 68.

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

Procedure: Starting from (S)-N5-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-ornithine, cyclohexanesulphonyl chloride and (S)-2-cyano-pyrrolidine hydrochloride, the expected product is obtained according to the procedure described in Example 3.

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

Procedure: Starting from (S)-N5-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-ornithine, methanesulphonyl chloride and (S)-2-cyano-pyrrolidine hydrochloride, the expected product is obtained according to the procedure described in Example 3.

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

Procedure: Starting from (S)-N2-(benzyloxycarbonyl)-arginine, methanesulphonyl chloride and (S)-2-cyano-pyrrolidine hydrochloride, the expected product is obtained according to the procedure described in Example 1.