1-amino-3-(2-phenylpropan-2-yl)thiourea

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

Procedure: A solution of 3-iodo-1-tosyl-1H-indole-5-carboxylic acid (1.330 g, 3.01 mmol), N-(2-phenylpropan-2-yl)hydrazinecarbothioamide (0.631 g, 3.01 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.156 g, 6.03 mmol) (Sigma-Aldrich) in DMF (5.0 mL) was heated at 80° C. for 2 h. The solution was cooled to RT. Water (precipitate formed), EtOAc and Celite were added, and the solids were removed by filtration and washed with EtOAc (3×). The organic layer was evaporated to reduce solvent volume. The aqueous layer was then extracted with EtOAc (2×50 mL). The combined organic layers were concentrated in vacuo, and the crude material was purified by flash chromatography (20-100% EtOAc in Hex) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (408.1 mg, 0.682 mmol, 22.62%). MS (ESI, pos. ion) m/z: 599.0 (M+1). the solids were removed by filtration washed with EtOAc (3×) The organic layer was evaporated The aqueous layer was then extracted with EtOAc (2×50 mL) The combined organic layers were concentrated in vacuo the crude material was purified by flash chromatography (20-100% EtOAc in Hex)

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

Procedure: Anhydrous hydrazine (1.161 mL, 37.0 mmol) (Sigma-Aldrich) was added to a stirring solution of (2-isothiocyanatopropan-2-yl)benzene (6.56 g, 37.0 mmol) in EtOH (150 mL). The reaction was stirred at RT for 2 h to give N-(2-phenylpropan-2-yl)hydrazinecarbothioamide. MS (ESI, pos. ion) m/z: 210.2 (M+1). The material was used without purification.

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

Procedure: Anhydrous hydrazine (1.161 mL, 37.0 mmol) (Sigma-Aldrich) was added to a stirring solution of (2-isothiocyanatopropan-2-yl)benzene (6.56 g, 37.0 mmol) in EtOH (150 mL). The reaction was stirred at RT for 2 h to give N-(2-phenylpropan-2-yl)hydrazinecarbothioamide. MS (ESI, pos. ion) m/z: 210.2 (M+1). The material was used without purification.

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

Procedure: A solution of 3-iodo-1-tosyl-1H-indole-5-carboxylic acid (1.330 g, 3.01 mmol), N-(2-phenylpropan-2-yl)hydrazinecarbothioamide (0.631 g, 3.01 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.156 g, 6.03 mmol) (Sigma-Aldrich) in DMF (5.0 mL) was heated at 80° C. for 2 h. The solution was cooled to RT. Water (precipitate formed), EtOAc and Celite were added, and the solids were removed by filtration and washed with EtOAc (3×). The organic layer was evaporated to reduce solvent volume. The aqueous layer was then extracted with EtOAc (2×50 mL). The combined organic layers were concentrated in vacuo, and the crude material was purified by flash chromatography (20-100% EtOAc in Hex) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (408.1 mg, 0.682 mmol, 22.62%). MS (ESI, pos. ion) m/z: 599.0 (M+1). the solids were removed by filtration washed with EtOAc (3×) The organic layer was evaporated The aqueous layer was then extracted with EtOAc (2×50 mL) The combined organic layers were concentrated in vacuo the crude material was purified by flash chromatography (20-100% EtOAc in Hex)

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

Procedure: Anhydrous hydrazine (1.161 mL, 37.0 mmol) (Sigma-Aldrich) was added to a stirring solution of (2-isothiocyanatopropan-2-yl)benzene (6.56 g, 37.0 mmol) in EtOH (150 mL). The reaction was stirred at RT for 2 h to give N-(2-phenylpropan-2-yl)hydrazinecarbothioamide. MS (ESI, pos. ion) m/z: 210.2 (M+1). The material was used without purification.