1,1,3-trimethyl-2,3-dihydroinden-4-amine

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

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

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

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

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

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

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

Procedure: A mixture of 1.5 g (11.9 mmols) of 2-methyl-3furan carboxylic acid with 3 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was cooled and 20 ml of ethyl acetate, 2 g (19.8 mmols) of triethylamine, and 1.8 g (10.3 mmols) of 1,1,3-trimethylindane-4-amine were added thereto. The resultant mixture was stirred at room temperature for 2 hours. The reaction solution was sequentially washed with water and brine. The organic layer consequently separated was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane, to obtain 1.8 g of white crystals (Compound No. 17 shown in Table 6). The yield was 65%. was refluxed for 1 hour The reaction solution was distilled under reduced pressure to remove excess thionyl chloride The obtained residue was cooled The reaction solution was sequentially washed with water and brine The organic layer consequently separated was dried with magnesium sulfate concentrated under reduced pressure The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane

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

Procedure: A mixture of 1.5 g (11.9 mmols) of 2-methyl-3furan carboxylic acid with 3 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was cooled and 20 ml of ethyl acetate, 2 g (19.8 mmols) of triethylamine, and 1.8 g (10.3 mmols) of 1,1,3-trimethylindane-4-amine were added thereto. The resultant mixture was stirred at room temperature for 2 hours. The reaction solution was sequentially washed with water and brine. The organic layer consequently separated was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane, to obtain 1.8 g of white crystals (Compound No. 17 shown in Table 6). The yield was 65%. was refluxed for 1 hour The reaction solution was distilled under reduced pressure to remove excess thionyl chloride The obtained residue was cooled The reaction solution was sequentially washed with water and brine The organic layer consequently separated was dried with magnesium sulfate concentrated under reduced pressure The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane

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

Procedure: A mixture of 1.5 g (10.4 mmols) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 5 ml of thionyl chloride, and one drop of pyridine was refluxed for 1 hour. The resultant solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was dissolved in 10 ml of ethyl acetate. This solution was added to 10 ml of ethyl acetate solution of 1.7 g (9.7 mmols) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine, and the resultant solution was stirred at room temperature for 3 hours. The resultant reaction solution was sequentially washed with water, aqueous sodium hydrogen carbonate solution, water, and a saturated brine, and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/9), to obtain 2.17 g of white crystals (Compound No. 14 shown in Table 6). The yield was 69.1%. was refluxed for 1 hour The resultant solution was distilled under reduced pressure to remove excess thionyl chloride The obtained residue was dissolved in 10 ml of ethyl acetate The resultant reaction solution was sequentially washed with water, aqueous sodium hydrogen carbonate solution, water a saturated brine, and then concentrated under reduced pressure The concentrated residue was separated purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/9)

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

Procedure: A mixture of 0.5 g (3.57 mmols) of 3-hydroxypyrazine-2-carboxylic acid, 3 ml of phosphorus oxychloride, and one drop of pyridine was refluxed for 3 hours. The resultant reaction solution was distilled to remove excess phosphorus oxychloride. To the residue 5 ml of ethyl acetate was added. The solution was added dropwise to 10 ml of an ethyl acetate solution of 0.53 g (3 mmols) of 4-amino-1,1,3-trimethylindane and 0.4 g (3.96 mmols) of triethylamine. The resultant mixture was stirred at room temperature for 2 hours and then sequentially washed with water, sodium hydrogen carbonate, water, and a saturated brine. The washed solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/4), to obtain 0.58 g of light yellow crystals (Compound No. 10 shown in Table 5). The yield was 61%. was refluxed for 3 hours The resultant reaction solution was distilled to remove excess phosphorus oxychloride To the residue 5 ml of ethyl acetate was added sequentially washed with water, sodium hydrogen carbonate, water The washed solution was dried with magnesium sulfate concentrated under reduced pressure The concentrated residue was separated purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/4)

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

Procedure: A mixture of 1.7 g (10.3 mmols) of 4-methyl-5-thiazole carboxylic acid and 10 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The residue was dissolved in 10 ml of ethyl acetate. The solution was added to 10 ml of an ethyl acetate solution of 1.8 g (10.3 mmols) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine, and the resultant solution was stirred at room temperature for 3 hours. The solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine. The solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2), to obtain 1.6 g of amorphous solid substance (Compound No. 6 shown in Table 4). The yield was 50.2%. was refluxed for 1 hour The reaction solution was distilled under reduced pressure to remove excess thionyl chloride The residue was dissolved in 10 ml of ethyl acetate The solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine The solution was dried with magnesium sulfate concentrated under reduced pressure The concentrated residue was separated purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2)

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

Procedure: A mixture of 1.7 g (10.3 mmols) of 4-methyl-5-thiazole carboxylic acid and 10 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The residue was dissolved in 10 ml of ethyl acetate. The solution was added to 10 ml of an ethyl acetate solution of 1.8 g (10.3 mmols) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine, and the resultant solution was stirred at room temperature for 3 hours. The solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine. The solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2), to obtain 1.6 g of amorphous solid substance (Compound No. 6 shown in Table 4). The yield was 50.2%. was refluxed for 1 hour The reaction solution was distilled under reduced pressure to remove excess thionyl chloride The residue was dissolved in 10 ml of ethyl acetate The solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine The solution was dried with magnesium sulfate concentrated under reduced pressure The concentrated residue was separated purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/2)