2-amino-7-substituted benzothiazole compound as well as preparation method and application thereof
A technology of benzothiazole and compounds, applied in the field of medicinal chemistry, can solve the problems of high cost, high medical expenses, and unsatisfactory effects, and achieve the effects of simple post-processing, high yield, and short reaction steps
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Embodiment 1
[0056] The synthesis of embodiment 1 2-amino-7-methylbenzothiazole
[0057] Dissolve 0.03mmol of 3-methylaniline in 12mL of acetic acid, add 30mmol of potassium thiocyanate and stir for 20 minutes. 5 mmol of bromine was dissolved in 0.3 mL of acetic acid, slowly added to the above-mentioned reactant, the reaction temperature in a water bath was 35°C, stirred overnight, filtered, and the precipitate was washed twice with 30 mL of ethyl acetate. Combine the filtrate and washing liquid, alkalinize it with ammonia solution, wash it 4 times with 50 mL concentrated brine, concentrate to 30 mL, apply flash chromatography, elute with n-hexane: acetone 4:1 (v / v), collect the eluate , and the solvent was evaporated to obtain 3.0 g of 2-amino-7-methylbenzothiazole with a yield of 61%. 1 H-NMR (CDCl 3 , 500MHz): δ2.38(m, 3H), 4.08(brs, 2H), 7.40(dd, J=8.6HzJ=2.3Hz, 1H), 7.49(d, J=2.3Hz, 1H), 7.68(d , J=8.6Hz, 1H); ESI-MS (m / z, %): 163.04 (M-H) - .
Embodiment 2
[0058] Example 2 Synthesis of 2-amino-7-ethylbenzothiazole
[0059] Dissolve 0.02mmol of 3-ethylaniline in 14mL of acetic acid, add 40mmol of potassium thiocyanate and stir for 15 minutes. 7mmol of bromine was dissolved in 0.4mL of acetic acid, slowly added to the above-mentioned reactant, the reaction temperature in a water bath was 40°C, stirred overnight, filtered, and the precipitate was washed 5 times with 10mL of ethyl acetate. Combine the filtrate and washing liquid, alkalinize it with ammonia solution, wash it with 60mL concentrated brine four times, concentrate to 20mL, apply flash chromatography, elute with n-hexane: acetone 6:1 (v / v), collect the eluate , and the solvent was evaporated to obtain 2.06 g of 2-amino-7-ethylbenzothiazole with a yield of 58%. 1 H-NMR (CDCl 3, 500MHz), δ1.02(t, J=2.4Hz, 3H), 2.06(m, 2H), 4.28(brs, 2H), 7.42(dd, J=8.0Hz, J=2.1Hz, 1H), 7.49 (d, J=2.1Hz, 1H), 7.65 (d, J=8.0Hz, 1H); ESI-MS (m / z, %): 177.06 (M-H) - .
Embodiment 3
[0060] Example 3 Synthesis of 2-amino-7-methoxybenzothiazole
[0061] Dissolve 0.04mmol of 3-methylaniline in 16mL of acetic acid, add 50mmol of potassium thiocyanate and stir for 10 minutes. 9 mmol of bromine was dissolved in 0.5 mL of acetic acid, slowly added to the above-mentioned reactant, the reaction temperature in a water bath was 30°C, stirred overnight, filtered, and the precipitate was washed 3 times with 20 mL of ethyl acetate. Combine the filtrate and washing liquid, alkalinize it with ammonia solution, wash it three times with 80 mL concentrated brine, concentrate to 40 mL, apply flash chromatography, elute with n-hexane: acetone 4:1 (v / v), collect the eluate , and the solvent was evaporated to obtain 5.32 g of 2-amino-7-methoxybenzothiazole with a yield of 64%. 1 H-NMR (CDCl 3 , 500MHz), δ2.32(s, 3H), 4.20(brs, 2H), 7.06(dd, J=8.3Hz, J=2.2Hz, 1H), 7.40(d, J=2.2Hz, 1H), 7.54 (d, J=8.3Hz, 1H); ESI-MS (m / z, %): 207.03 (M-H) - .
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