N-(dimethoxymethyl)-N-methylethanamine

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

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

Procedure: 0.30 g (0.81 mmol) of 4-({3-[1-(4-chlorophenyl)cyclopropyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylaniline is dissolved in 3 ml of toluene and 0.75 ml of methanol and treated with 0.32 g (2.42 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 18 h, subsequently cooled, freed from the solvent under vacuum and purified by column chromatography. 0.22 g of product is obtained (99.3% purity, 61.7% yield; log P (pH2.3)=2.28). The reaction mixture is refluxed for 18 h subsequently cooled purified by column chromatography

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

Procedure: 1.85 g (5.15 mmol) of 4-{[3-(3-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline are dissolved in 10 ml of toluene and treated with 1.37 g (10.31 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 12 h, subsequently cooled, freed of solvent under vacuum and purified by column chromatography. 0.59 g of product is obtained (99.0% purity, 27.3% yield; log P (pH2.3)=2.31). The reaction mixture is refluxed for 12 h subsequently cooled purified by column chromatography

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

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

Procedure: A solution of 1.80 g (4.87 mmol) of 5-(4-amino-2,5-dimethylphenoxy)-3-(4-chlorobenzyl)isothiazole-4-carbonitrile and 0.91 g (6.8 mmol) of N-(dimethoxymethyl)-N-methylethanamine in 60 ml of toluene is stirred at 80° C. for 22 h. Another 0.91 g (6.8 mmol) of N-(dimethoxymethyl)-N-methylethanamine is added, and the solution is then stirred for a further 22 h.

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

Procedure: 0.30 g (0.81 mmol) of 4-({3-[1-(4-chlorophenyl)cyclopropyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylaniline is dissolved in 3 ml of toluene and 0.75 ml of methanol and treated with 0.32 g (2.42 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 18 h, subsequently cooled, freed from the solvent under vacuum and purified by column chromatography. 0.22 g of product is obtained (99.3% purity, 61.7% yield; log P (pH2.3)=2.28). The reaction mixture is refluxed for 18 h subsequently cooled purified by column chromatography

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

Procedure: 1.85 g (5.15 mmol) of 4-{[3-(3-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline are dissolved in 10 ml of toluene and treated with 1.37 g (10.31 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 12 h, subsequently cooled, freed of solvent under vacuum and purified by column chromatography. 0.59 g of product is obtained (99.0% purity, 27.3% yield; log P (pH2.3)=2.31). The reaction mixture is refluxed for 12 h subsequently cooled purified by column chromatography

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

Procedure: 1.85 g (5.15 mmol) of 4-{[3-(3-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline are dissolved in 10 ml of toluene and treated with 1.37 g (10.31 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 12 h, subsequently cooled, freed of solvent under vacuum and purified by column chromatography. 0.59 g of product is obtained (99.0% purity, 27.3% yield; log P (pH2.3)=2.31). The reaction mixture is refluxed for 12 h subsequently cooled purified by column chromatography

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

Procedure: To a mixture of 310 mg (0.8 mmol) of 4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethyl-aniline in 20 ml acetonitrile 208 mg (1.5 mmol) of N-(dimethoxymethyl)-N-methylethanamine (77% pure) was added. The reaction mixture was refluxed for 20 hrs. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo yielded 220 mg (59%) with a purity of 72% log P (pH=2.3)=1.45. was added The reaction mixture was refluxed for 20 hrs The reaction mixture was concentrated in vacuo diluted with ethyl acetate washed with water The organic layer was dried over magnesium sulfate concentrated in vacuo yielded 220 mg (59%) with a purity of 72% log P (pH=2.3)=1.45

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 293 mg (0.7 mmol) of 4-[2-(3-chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine in 20 ml methanol 182 mg (1.05 mmol) of N-(dimethoxymethyl)-N-methyl-ethanamine (77% pure) was added. The reaction mixture was stirred for 20 hrs at 45° C. The reaction mixture was dried over magnesium sulfate concentrated in vacuo and yielded 290 mg (76%) with a purity of 78%; log P (pH 2.3)=2.08. was added The reaction mixture was dried over magnesium sulfate concentrated in vacuo yielded 290 mg (76%) with a purity of 78%

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

Procedure: To a mixture of 310 mg (0.8 mmol) of 4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethyl-aniline in 20 ml acetonitrile 208 mg (1.5 mmol) of N-(dimethoxymethyl)-N-methylethanamine (77% pure) was added. The reaction mixture was refluxed for 20 hrs. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo yielded 220 mg (59%) with a purity of 72% log P (pH=2.3)=1.45. was added The reaction mixture was refluxed for 20 hrs The reaction mixture was concentrated in vacuo diluted with ethyl acetate washed with water The organic layer was dried over magnesium sulfate concentrated in vacuo yielded 220 mg (59%) with a purity of 72% log P (pH=2.3)=1.45

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 293 mg (0.7 mmol) of 4-[2-(3-chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine in 20 ml methanol 182 mg (1.05 mmol) of N-(dimethoxymethyl)-N-methyl-ethanamine (77% pure) was added. The reaction mixture was stirred for 20 hrs at 45° C. The reaction mixture was dried over magnesium sulfate concentrated in vacuo and yielded 290 mg (76%) with a purity of 78%; log P (pH 2.3)=2.08. was added The reaction mixture was dried over magnesium sulfate concentrated in vacuo yielded 290 mg (76%) with a purity of 78%