Method for preparing isoquinoline hydrochloride intermediate and rho kinase inhibitor by using btc/ph3po chlorination system
A technology of kinase inhibitor and sulfonyl chloride hydrochloride, which is applied in the field of medicine, can solve the problems of potential safety hazards in storage and transportation, environmental pollution of by-product sulfides, low reaction efficiency of chlorinated reagents, etc. The effect of high product yield and high product quality
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Embodiment 1
[0046] Embodiment 1: the synthesis of isoquinoline-5-sulfonyl chloride hydrochloride
[0047] With isoquinoline-5-sulfonic acid (31.38g, 150mmol), BTC (14.84g, 50mmol), Ph 3 PO (2.09g, 7.5mmol) and ethyl acetate (300mL) were added to a 500mL reaction flask, heated to 25°C for 1 hour, cooled down to room temperature, added dichloromethane (150mL) and stirred, and suction filtered to obtain a white solid. Vacuum-dried at 40°C-50°C to obtain 33.68g of solid, with a yield of 85% and an HPLC content of 99.92%. After the filtrate part is concentrated, Ph is precipitated at low temperature 3 PO (precipitation temperature at low temperature is 30°C, the same below), after washing with a small amount of petroleum ether, suction filtration, and drying to obtain Ph 3 PO (1.91g) is reusable.
Embodiment 2
[0048] Embodiment 2: the synthesis of isoquinoline-5-sulfonyl chloride hydrochloride
[0049] With isoquinoline-5-sulfonic acid (31.38g, 150mmol), BTC (14.84g, 50mmol), Ph 3 PO (2.09g, 7.5mmol) and ethyl acetate (300mL) were added to a 500mL reaction flask, heated to 25°C for 5 hours, cooled to room temperature, added dichloromethane (150mL) and stirred, and suction filtered to obtain a white solid. Vacuum-dried at 40°C-50°C to obtain 34.86g of solid, with a yield of 88% and an HPLC content of 99.95%. After the filtrate part is concentrated, Ph is precipitated at low temperature 3 PO, washed with a small amount of petroleum ether, suction filtered, and dried to obtain Ph 3 PO (2.01g) is reusable.
Embodiment 3
[0050] Embodiment 3: the synthesis of isoquinoline-5-sulfonyl chloride hydrochloride
[0051] With isoquinoline-5-sulfonic acid (31.38g, 150mmol), BTC (14.84g, 50mmol), Ph 3 PO (2.09g, 7.5mmol) and ethyl acetate (300mL) were added to a 500mL reaction flask, heated to 25°C for 14 hours, cooled to room temperature, added dichloromethane (150mL) and stirred, suction filtered to obtain a white solid, Vacuum-dried at 40°C-50°C to obtain 34.47g of solid, with a yield of 87% and an HPLC content of 99.94%. After the filtrate part is concentrated, Ph is precipitated at low temperature 3 PO, washed with a small amount of n-hexane, suction filtered and dried to obtain Ph 3 PO (1.89g) is reusable.
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