2-(tert-butylamino)ethanol

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

Procedure: A solution of 2-[(benzyloxy)methyl]oxirane (350 mg) and 2-(tert-butylamino)ethanol (500 mg) in ethanol (20 mL) was heated to reflux temperature and left at this temperature overnight. The solution was concentrated at reduced pressure. The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane. This gave the title compound as a colourless oil (501 mg) to reflux temperature The solution was concentrated at reduced pressure The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane

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

Procedure: To a solution of 8.7 ml (0.10 mol) of phosphorus trichloride in 200 ml of toluene in a 500 ml three neck flask equipped with a mechanical stirrer, a condenser and an addition funnel is added a solution of 11.72 g (0.10 mol) of 2-tert-butylaminoethanol in 50 ml of toluene. After refluxing for 16 hours, the orange solids are filtered off and the filtrate concentrated in vacuo. Distillation under reduced pressure gives 10.3 g (56.7%) of clear liquid: b.p. 82° C./1.0 mm Hg. After refluxing for 16 hours the orange solids are filtered off the filtrate concentrated in vacuo Distillation under reduced pressure

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

Procedure: A solution of 2-[(benzyloxy)methyl]oxirane (350 mg) and 2-(tert-butylamino)ethanol (500 mg) in ethanol (20 mL) was heated to reflux temperature and left at this temperature overnight. The solution was concentrated at reduced pressure. The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane. This gave the title compound as a colourless oil (501 mg) to reflux temperature The solution was concentrated at reduced pressure The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane

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

Procedure: (5Z)-3-[2-(tert-Butylamino)ethyl]-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-1,3-thiazolidine-2,4-dione was prepared from [(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine (from Example 1) and 2-(N-tert-butylamino)ethanol following General Procedure J.

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

Procedure: (5Z)-3-[2-(tert-Butylamino)ethyl]-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-1,3-thiazolidine-2,4-dione was prepared from [(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine (from Example 1) and 2-(N-tert-butylamino)ethanol following General Procedure J.

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

Procedure: 1.43 g of 2-phenylbenzofuran-7-carboxylic acid are dissolved in 10 ml of tetrahydrofuran, and 1.08 g of carbonyldiimidazole are added to the solution. The mixture is stirred at room temperature for 2 hours and a solution of 0.76 g of 2-(t-butylamino)ethanol in 4 ml of tetrahydrofuran is added thereto. The mixture is stirred at room temperature for 15 hours and evaporated to remove solvent. Water is added to the residue and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried, and evaporated to remove solvent to give 1.72 g of 2-(t-butylamino)ethyl 2-phenylbenzofuran-7-carboxylate as pale yellow oil. The mixture is stirred at room temperature for 15 hours evaporated to remove solvent Water is added to the residue the aqueous mixture is extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent

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

Procedure: To a solution of 50 mg (0.12 mmol) 17-hydroxywortmannin in 0.5 mL CH2Cl2 is added 28.1 mg (0.24 mmol) 2-(tert-butylamino)-ethanol. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with diethyl ether (Et2O) to give 32 mg (48.7%) product as an orange powder. MS (ESI) m/z 548.3 (M+1). CH2Cl2 is removed in vacuo The residue is triturated with diethyl ether (Et2O)

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

Procedure: To a solution of 8.7 ml (0.10 mol) of phosphorus trichloride in 200 ml of toluene in a 500 ml three neck flask equipped with a mechanical stirrer, a condenser and an addition funnel is added a solution of 11.72 g (0.10 mol) of 2-tert-butylaminoethanol in 50 ml of toluene. After refluxing for 16 hours, the orange solids are filtered off and the filtrate concentrated in vacuo. Distillation under reduced pressure gives 10.3 g (56.7%) of clear liquid: b.p. 82° C./1.0 mm Hg. After refluxing for 16 hours the orange solids are filtered off the filtrate concentrated in vacuo Distillation under reduced pressure

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

Procedure: A solution of 2-[(benzyloxy)methyl]oxirane (350 mg) and 2-(tert-butylamino)ethanol (500 mg) in ethanol (20 mL) was heated to reflux temperature and left at this temperature overnight. The solution was concentrated at reduced pressure. The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane. This gave the title compound as a colourless oil (501 mg) to reflux temperature The solution was concentrated at reduced pressure The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane

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

Procedure: To a solution of 8.7 ml (0.10 mol) of phosphorus trichloride in 200 ml of toluene in a 500 ml three neck flask equipped with a mechanical stirrer, a condenser and an addition funnel is added a solution of 11.72 g (0.10 mol) of 2-tert-butylaminoethanol in 50 ml of toluene. After refluxing for 16 hours, the orange solids are filtered off and the filtrate concentrated in vacuo. Distillation under reduced pressure gives 10.3 g (56.7%) of clear liquid: b.p. 82° C./1.0 mm Hg. After refluxing for 16 hours the orange solids are filtered off the filtrate concentrated in vacuo Distillation under reduced pressure