N',2-dihydroxypropanimidamide

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 6.45 g crude N′,2-dihydroxypropanimidamide was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g of crude title compound, which was used directly in the next step for 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol. LC-MS (M++1): 243 washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave by drying in vacuo 27.24 g of crude title compound, which

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

実験手順: The title compound from Example 1 (6.45 g) was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g, which was directly used in the next step. The material was dissolved in ethanol (250 mL) and refluxed for 1 h, followed by addition of 14.0 g (170 mmol) sodium acetate in water (40 mL). After refluxing over night, cooling to RT and addition of water (250 mL) the mixture was concentrated in vacuo to about half of its volume, resulting in a precipitate which was filtered off and recrystallized from EtOAc/heptane to yield 6.45 g (25%) of the title compound. washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave by drying in vacuo 27.24 g, which The material was dissolved in ethanol (250 mL) refluxed for 1 h After refluxing over night cooling to RT was concentrated in vacuo to about half of its volume resulting in a precipitate which was filtered off recrystallized from EtOAc/heptane

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

実験手順: The title compound from Example 1 (6.45 g) was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g, which was directly used in the next step. The material was dissolved in ethanol (250 mL) and refluxed for 1 h, followed by addition of 14.0 g (170 mmol) sodium acetate in water (40 mL). After refluxing over night, cooling to RT and addition of water (250 mL) the mixture was concentrated in vacuo to about half of its volume, resulting in a precipitate which was filtered off and recrystallized from EtOAc/heptane to yield 6.45 g (25%) of the title compound. washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave by drying in vacuo 27.24 g, which The material was dissolved in ethanol (250 mL) refluxed for 1 h After refluxing over night cooling to RT was concentrated in vacuo to about half of its volume resulting in a precipitate which was filtered off recrystallized from EtOAc/heptane

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 6.45 g crude N′,2-dihydroxypropanimidamide was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g of crude title compound, which was directly used in the next step. LC-MS (M++1): 243. washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave by drying in vacuo 27.24 g of crude title compound, which

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

実験手順: 6.45 g crude N′,2-dihydroxypropanimidamide was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g of crude title compound, which was used directly in the next step for 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol. LC-MS (M++1): 243 washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave by drying in vacuo 27.24 g of crude title compound, which

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

実験手順: The title compound from Example 1 (6.45 g) was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g, which was directly used in the next step. The material was dissolved in ethanol (250 mL) and refluxed for 1 h, followed by addition of 14.0 g (170 mmol) sodium acetate in water (40 mL). After refluxing over night, cooling to RT and addition of water (250 mL) the mixture was concentrated in vacuo to about half of its volume, resulting in a precipitate which was filtered off and recrystallized from EtOAc/heptane to yield 6.45 g (25%) of the title compound. washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave by drying in vacuo 27.24 g, which The material was dissolved in ethanol (250 mL) refluxed for 1 h After refluxing over night cooling to RT was concentrated in vacuo to about half of its volume resulting in a precipitate which was filtered off recrystallized from EtOAc/heptane