1-(aminomethyl)cyclopentanol hydrochloride

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

Procedure: The title compound was prepared using 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid [prepared from 3-(trifluoromethoxy)benzyl bromide and ethyl 5-cyanoindole-2-carboxylate] and 1-aminomethyl-cyclopentanol hydrochloride in a manner similar to that described in Example 11.

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

Procedure: The title compound was prepared using 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid [prepared from 3-(trifluoromethoxy)benzyl bromide and ethyl 5-cyanoindole-2-carboxylate] and 1-aminomethyl-cyclopentanol hydrochloride in a manner similar to that described in Example 11.

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

Procedure: The title compound was prepared according to the procedure described in Step A of Example 5 from 1-fluoro-4-(methylsulfonyl)-2-nitrobenzene (Acros Organics) and 1-(aminomethyl)cyclopentanol hydrochloride (J. Med. Chem. 1981, 24, 7-12).

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

Procedure: The mixture of 2,5-dibromonitrobenzene (Tokyo Kasei Kogyo Co., Ltd., 5.4 g, 19.2 mmol), 1-(aminomethyl)cyclopentanol hydrochloride (J. Med. Chem. 1981, 24, 12-16, 4.3 g, 28.4 mmol) and N,N-diisopropylethylamine (8.4 mL, 48.1 mmol) in 1-methyl-2-pyrrolidinone (32 mL) was microwaved for 30 min at 200° C. The reaction was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (2.6 g, 43%) as an orange amorphous solid. was microwaved for 30 min at 200° C The reaction was quenched with water extracted three times with ethyl acetate The combined organic layers were dried over sodium sulfate filtered The filtrate was concentrated the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent)

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

Procedure: The title compound was prepared according to the procedure described in Step A of Example 5 from 1-chloro-4-(ethylsulfonyl)-2-nitrobenzene (Step C of Example 2), 1-(aminomethyl)cyclopentanol hydrochloride (J. Med. Chem. 1981, 24, 12-16) and triethylamine.

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

Procedure: The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-fluorophenylboronic acid and 1-aminomethyl-cyclopentanol hydrochloride (CAS [76066-27-8]) as starting materials to yield 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(1-hydroxy-cyclopentylmethyl)-nicotinamide. MS (ISP) 385.3 (M+H)+. The title compound was synthesized in analogy to Example 75

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

Procedure: The title compound was synthesized in analogy to Example 54, using 5-Cyclopropyl-4-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 42c) and 1-(aminomethyl)cyclopentanol hydrochloride (CAN 76066-27-8) as starting materials and isolated (71 mg, 63%) as a white solid; MS (ESI, m/z): 331.0 (M+H+). isolated (71 mg, 63%) as a white solid