4-methyl-N-(3-methylbutyl)cyclohexan-1-amine

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An equimolar mixture of 1,1-carbonyldiimidazole, (2-amino-thiazole-5-sulfonylamino)-acetic acid ethyl ester and DMAP (5 mol %) in THF was heated for 5 h at 50-60° C. and then cooled to room temperature. Then (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine (1 equivalent; prepared following the procedure described in the preparation of [2-(3-cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was dissolved in MeCN and purified using HPLC to give {2-[3-(3-methyl-butyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester as crystals. cooled to room temperature prepared was added The reaction mixture was quenched with water The organic phase was isolated the aqueous phase was extracted with CH2Cl2 the combined organic phases were dried concentrated in vacuo The crude product was dissolved in MeCN purified

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-trans-methyl-cyclohexylamine hydrochloride (15 g, 100 mmol) in THF-MeOH (2:1, 200 mL) was added solid NaOH (6.01 g, 150 mmol). The mixture was stirred for 30 m before isovaleraldehyde (10.4 g, 120 mmol), 20 mL AcOH was added. Subsequently sodium cyanoborohydride (6.0 g, 150 mmol) was added in small portions. The reaction mixture was stirred for 18 h before H2O (200 mL) was added and the mixture was extracted with DCM (2×100 mL). The organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether were added. The solvent were removed in vacuo and diethyl ether was added (200 mL). The precipitate was filtered off washed with diethyl ether and dried in vacuo to give 18.8 g of (3-methyl-butyl) -(4-methyl-cyclohexyl)-amine. was added was added the mixture was extracted with DCM (2×100 mL) The organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether were added The solvent were removed in vacuo and diethyl ether was added (200 mL) The precipitate was filtered off washed with diethyl ether dried in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-trans-methyl-cyclohexylamine hydrochloride (15 g, 100 mmol) in THF-MeOH (2:1, 200 mL) was added solid NaOH (6.01 g, 150 mmol). The mixture was stirred for 30 m before isovaleraldehyde (10.4 g, 120 mmol), 20 mL AcOH was added. Subsequently sodium cyanoborohydride (6.0 g, 150 mmol) was added in small portions. The reaction mixture was stirred for 18 h before H2O (200 mL) was added and the mixture was extracted with DCM (2×100 mL). The organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether were added. The solvent were removed in vacuo and diethyl ether was added (200 mL). The precipitate was filtered off washed with diethyl ether and dried in vacuo to give 18.8 g of (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine. was added was added the mixture was extracted with DCM (2×100 mL) The organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether were added The solvent were removed in vacuo and diethyl ether was added (200 mL) The precipitate was filtered off washed with diethyl ether dried in vacuo

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An equimolar mixture of 1,1-carbonyldiimidazole, (2-amino-thiazole-5-sulfonylamino)-acetic acid ethyl ester and DMAP (5 mol %) in THF was heated for 5 h at 50-60° C. and then cooled to room temperature. Then (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine (1 equivalent; prepared following the procedure described in the preparation of [2-(3-cyclohexyl-3-phenethyl-ureido)-thiazol-5-ylsulfanyl]-acetic acid) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was dissolved in MeCN and purified using HPLC to give {2-[3-(3-methyl-butyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester as crystals. cooled to room temperature prepared was added The reaction mixture was quenched with water The organic phase was isolated the aqueous phase was extracted with CH2Cl2 the combined organic phases were dried concentrated in vacuo The crude product was dissolved in MeCN purified