Benzimidazolone compounds
a technology of benzimidazolone and compounds, applied in the field of benzimidazolone compounds, can solve the problems of untold amount of suffering, and achieve the effect of sufficient time for metabolism
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example 1
Synthesis of “trans” Head Groups
[0156]
Procedure:
[0157] A mixture of compound 1 (22.8 g, 200 mmol), compound 2 (19.9 g, 100 mmol) and Na(OAc)3BH (29.7 g, 140 mmol) in 300 mL 1,2-dichloroethane was stirred overnight. The reaction was quenched with aqueous K2CO3. The mixture was extracted with Et2O (3×), and the organic extracts were dried over K2CO3, filtered and the solvent was evaporated. The crude product was purified by column chromatography (10% Et3N, 40% EtOAc in hexane, then 10% Et3N, 90% EtOAc, and then 10% MeOH, 90% EtOAc) to give pure 3 as a solid (18.80 g, 63.6%).
[0158] MS: m / z 298.3 (M+1)
[0159]1H-NMR (CDCl3): d 0.90 (m, 1H), 1.05-1.40 (m, 6H), 1.45 (s, 9H), 1.68-1.80 (m, 5H), 1.88 (m, 2H), 2.05 (m, 1H), 2.15 (m, 1H), 2.30 (m, 1H), 2.70-2.90 (m, 3H), 4.00 (b, 2H).
[0160] To a solution of compound 3 (18.8 g, 63 mmol) in 50 mL of CH3CN was added 1,1′-carbonyldiimidazole (12.82 g, 79 mmol). Gas was evolved and the mixture became a slurry in a few min and then a solid afte...
example 2
Synthesis of “cis” Head Groups
[0171]
Procedure:
[0172] In a manner similar to the preparation of 7, compound 12 was prepared.
example 3
Attachment of Tail Groups
[0173] Tail groups were attached to the head groups according to the following procedures:
General Procedure for Alkylation:
[0174] To a solution of the amine (1 eq) and triethylamine (1 eq) in dimethylformamide, was added 1 eq of alkyl bromide or chloride in one portion. The mixture was stirred and heated at 80° C. over night. TLC indicated the reaction was complete. The reaction was quenched by the addition of water followed by 1 N NaOH to pH 10. The mixture was extracted 2× with Et2O. The combined organic extracts were dried over potassium carbonate and the solvent evaporated, followed by chromatography to give the pure product.
General Procedure for Reductive Amination:
[0175] To a mixture of ketone or aldehyde (1 eq), amine (1 eq), and acetic acid (1 eq) in methanol, was added sodium cyanoborohydride (1.4 eq) in one portion. The mixture was stirred over night at room temperature. TLC indicated the reaction was complete. The reaction was quenched by ...
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