cyclopentylthiourea

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The t-butyl-cyclopentylthiourea (3.70 g) was dissolved in concentrated HCl (46 mL). The dark yellow solution was set to a gentle reflux. After 40 min, the reaction mixture was allowed to cool. The volume was concentrated to approx. half under reduced pressure, cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3. The product was extracted into EtOAc (3×), the combined EtOAc extracts were washed with H2O (2×) and brine (1×). The organic layer was dried over anhydrous MgSO4, filtered and evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude). Trituration of the crude material in hexane/EtOAc 95/5 provided, after filtration, the N-cyclopentylthiourea as a white solid (2.38; 90% yield). to cool The volume was concentrated to approx. half under reduced pressure cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3 The product was extracted into EtOAc (3×) the combined EtOAc extracts were washed with H2O (2×) and brine (1×) The organic layer was dried over anhydrous MgSO4 filtered evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude)

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

Procedure: Isothiocyanato-cyclopentane (4 g) in ammonia (37% in water, 8 mL) and methanol (32 mL) was stirred for 16 hours, filtered of and dried. The Cyclopentyl-thiourea (2.06 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.06 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The mixture was then cooled to room temperature and filtered. The solid was washed with a small amount of diethylether and dried. m/z=289.05 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification. filtered of and dried was heated to 80° C. for 2 hours The mixture was then cooled to room temperature filtered The solid was washed with a small amount of diethylether dried used in the next step without any further purification

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

Procedure: Isothiocyanato-cyclopentane (4 g) in ammonia (37% in water, 8 mL) and methanol (32 mL) was stirred for 16 hours, filtered of and dried. The Cyclopentyl-thiourea (2.06 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.06 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The mixture was then cooled to room temperature and filtered. The solid was washed with a small amount of diethylether and dried. m/z=289.05 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification. filtered of and dried was heated to 80° C. for 2 hours The mixture was then cooled to room temperature filtered The solid was washed with a small amount of diethylether dried used in the next step without any further purification

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

Procedure: The t-butyl-cyclopentylthiourea (3.70 g) was dissolved in concentrated HCl (46 mL). The dark yellow solution was set to a gentle reflux. After 40 min, the reaction mixture was allowed to cool. The volume was concentrated to approx. half under reduced pressure, cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3. The product was extracted into EtOAc (3×), the combined EtOAc extracts were washed with H2O (2×) and brine (1×). The organic layer was dried over anhydrous MgSO4, filtered and evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude). Trituration of the crude material in hexane/EtOAc 95/5 provided, after filtration, the N-cyclopentylthiourea as a white solid (2.38; 90% yield). to cool The volume was concentrated to approx. half under reduced pressure cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3 The product was extracted into EtOAc (3×) the combined EtOAc extracts were washed with H2O (2×) and brine (1×) The organic layer was dried over anhydrous MgSO4 filtered evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude)

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

Procedure: Isothiocyanato-cyclopentane (4 g) in ammonia (37% in water, 8 mL) and methanol (32 mL) was stirred for 16 hours, filtered of and dried. The Cyclopentyl-thiourea (2.06 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.06 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The mixture was then cooled to room temperature and filtered. The solid was washed with a small amount of diethylether and dried. m/z=289.05 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification. filtered of and dried was heated to 80° C. for 2 hours The mixture was then cooled to room temperature filtered The solid was washed with a small amount of diethylether dried used in the next step without any further purification

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amine was prepared following procedure B using cyclopentyl-thiourea (1.6 g, 10.7 mmol) and 2-bromo-1-(4-isopropyl-phenyl)-ethanone (2.6 g, 10.7 mmol). Purification (Silica gel, ethyl acetate/hexane 5:95) provided the product (2.9 g). LCMS m/z: 287 (M+1)+. Purification (Silica gel, ethyl acetate/hexane 5:95)

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

Procedure: Cyclopentyl-thiourea was prepared following procedure D using cyclopentyl amine (2.4 g, 28 mmol), and Fmoc-isothiocyanate (5.6 g, 20 mmol). Purification (Silica gel, ethyl acetate/hexane 1:1, 100%) provided the product (1.6 g) as white a solid. LCMS m/z: 145 (M+1)+. Purification (Silica gel, ethyl acetate/hexane 1:1, 100%)

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

Procedure: The t-butyl-cyclopentylthiourea (3.70 g) was dissolved in concentrated HCl (46 mL). The dark yellow solution was set to a gentle reflux. After 40 min, the reaction mixture was allowed to cool. The volume was concentrated to approx. half under reduced pressure, cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3. The product was extracted into EtOAc (3×), the combined EtOAc extracts were washed with H2O (2×) and brine (1×). The organic layer was dried over anhydrous MgSO4, filtered and evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude). Trituration of the crude material in hexane/EtOAc 95/5 provided, after filtration, the N-cyclopentylthiourea as a white solid (2.38; 90% yield). to cool The volume was concentrated to approx. half under reduced pressure cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3 The product was extracted into EtOAc (3×) the combined EtOAc extracts were washed with H2O (2×) and brine (1×) The organic layer was dried over anhydrous MgSO4 filtered evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude)