Compound containing sulfonamide structure, preparation method and application of compound, pharmaceutical composition and application of pharmaceutical composition
A technology containing sulfonamides and compounds, applied to compounds containing sulfonamide structures and their preparation, pharmaceutical compositions and application fields
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preparation example 1
[0093] Preparation Example 1: This preparation example is used to illustrate the synthesis process of the hydrochloride salt of Compound 1
[0094]
[0095] Step 1: Preparation of 5-bromo-1H-pyrrole-3-carbaldehyde
[0096] Pyrrole-3-carboxaldehyde (52.6mmol) and tetrahydrofuran (THF, 100mL) were added to a double-necked round bottom flask and placed in a low-temperature magnetic stirrer to cool to -78°C, and dissolved in N,N-dimethylformamide Bromosuccinimide (NBS, 52.6 mmol) in (DMF, 30 mL) was added dropwise into the reaction system. After the dropwise addition was completed and the reaction was continued for 1 h, the temperature was raised to -10° C. and the reaction was continued for 1 h. TLC monitored the complete reaction of the starting material. Add ice water to the system, extract with ethyl acetate (200mL×2), wash with saturated brine (150mL×2), combine the organic phases, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a brow...
preparation example 2
[0108] Preparation Example 2: This preparation example is used to illustrate the synthesis process of the hydrochloride salt of Compound 2
[0109] The preparation method of this preparation example is similar to preparation example 1, and difference is:
[0110] Replace the (2S)-1,4-dioxane-2-methanol in step 6) with an equimolar amount of cyclobutylmethanol to obtain the hydrochloride salt of compound 2, a white solid, the one-step yield in step 6). rate 24%.
[0111] 1 H NMR (600MHz, Methanol-d 4 )δ8.87–8.83(m,1H),8.61(s,1H),8.01(d,J=8.4Hz,1H),7.80(s,1H),7.68–7.63(m,1H),7.00(t ,J=8.4Hz,1H),6.76(d,J=8.4Hz,1H),6.69–6.62(m,1H),6.40(d,J=1.8Hz,1H),4.10(s,2H),4.00 (d,J=6.6Hz,2H),2.86–2.77(m,1H),2.72(s,3H),2.23–2.11(m,2H),2.08–1.89(m,4H).
preparation example 3
[0112] Preparation Example 3: This preparation example is used to illustrate the synthesis process of the hydrochloride salt of compound 3
[0113] The preparation method of this preparation example is similar to preparation example 1, and difference is:
[0114] The (2S)-1,4-dioxane-2-methanol in step 6) was replaced by an equimolar amount of cyclopentylmethanol to obtain the hydrochloride salt of compound 3, a white solid, the one-step yield in step 6). rate 31%.
[0115] 1 H NMR (600MHz, Methanol-d 4 )δ8.87(d, J=4.8Hz, 1H), 8.63(s, 1H), 8.05(d, J=8.4Hz, 1H), 7.81(d, J=2.4Hz, 1H), 7.72–7.66( m,1H),7.00(t,J=8.4Hz,1H),6.76(d,J=8.4Hz,1H),6.67(d,J=11.4Hz,1H),6.41(d,J=1.8Hz, 1H), 4.10(s, 2H), 3.92(d, J=6.6Hz, 2H), 2.72(s, 3H), 2.44–2.32(m, 1H), 1.92–1.83(m, 2H), 1.75–1.58 (m,4H),1.47–1.35(m,2H).
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