2-benzylsulfanyl-2-methylpropan-1-amine

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

Procedure: A solution of 2-benzylthio-1-nitro-2-methylpropane (19 g) in dry ether (75 cm3) was added dropwise over a period of about 1 h to a stirred suspension of lithium aluminium hydride (9.6 g) in dry ether (500 cm3), cooled in an ice bath. When the addition was complete the mixture was heated under reflux for an additional hour. Excess lithium aluminium hydride was destroyed by the careful addition of water, and then an aqueous solution of sodium potassium tartrate (500 cm3, 20% w/w) was added. The mixture was stirred until the solids had dissolved and the ether layer was then separated. The aqueous solution was then extracted with ether (3×50 cm3) and the combined extracts then dried (MgSO4). Removal of the ether under reduced pressure gave the crude product which was purified via recrystallisation of its hydrochloride salt from isopropanol. The purified amine (7.5 g, 46%) was obtained as a yellow oil. cooled in an ice bath When the addition was heated under reflux for an additional hour Excess lithium aluminium hydride was destroyed by the careful addition of water an aqueous solution of sodium potassium tartrate (500 cm3, 20% w/w) was added had dissolved the ether layer was then separated The aqueous solution was then extracted with ether (3×50 cm3) the combined extracts then dried (MgSO4) Removal of the ether under reduced pressure gave the crude product which was purified via recrystallisation of its hydrochloride salt from isopropanol

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

Procedure: To a mixture of 5-fluoro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.20 g), 2-(benzylthio)-2-methylpropylamine (0.13 g), 1H-1,2,3-benzotriazol-1-ol (0.11 g) and N,N-dimethylformamide (10 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.14 g) at 4° C., and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:8-4:6) to give the title compound (220 mg, crude yield 72%) as pale-purple crystals. washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

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

Procedure: To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.70 g), 2-(benzylthio)-2-methylpropylamine (0.47 g), 1H-1,2,3-benzotriazol-1-ol (0.35 g) and N,N-dimethylformamide (15 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.50 g) at 0° C., and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.86 g, yield 77%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:9-42:3, volume ratio). melting point 170-171° C. the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried (MgSO4) concentrated

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

Procedure: A solution of 2-benzylthio-1-nitro-2-methylpropane (19 g) in dry ether (75 cm3) was added dropwise over a period of about 1 h to a stirred suspension of lithium aluminium hydride (9.6 g) in dry ether (500 cm3), cooled in an ice bath. When the addition was complete the mixture was heated under reflux for an additional hour. Excess lithium aluminium hydride was destroyed by the careful addition of water, and then an aqueous solution of sodium potassium tartrate (500 cm3, 20% w/w) was added. The mixture was stirred until the solids had dissolved and the ether layer was then separated. The aqueous solution was then extracted with ether (3×50 cm3) and the combined extracts then dried (MgSO4). Removal of the ether under reduced pressure gave the crude product which was purified via recrystallisation of its hydrochloride salt from isopropanol. The purified amine (7.5 g, 46%) was obtained as a yellow oil. cooled in an ice bath When the addition was heated under reflux for an additional hour Excess lithium aluminium hydride was destroyed by the careful addition of water an aqueous solution of sodium potassium tartrate (500 cm3, 20% w/w) was added had dissolved the ether layer was then separated The aqueous solution was then extracted with ether (3×50 cm3) the combined extracts then dried (MgSO4) Removal of the ether under reduced pressure gave the crude product which was purified via recrystallisation of its hydrochloride salt from isopropanol