Dopamine D4 receptor ligand and preparation method thereof
A dopamine and receptor technology, applied in the field of dopamine D4 receptor ligands, can solve problems such as unsatisfactory selectivity, affinity or pharmacological properties, and achieve high affinity, simple process and product yield and high purity
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[0016] Example 1: Synthesis of 2-(3-(4-(4-fluorobenzyl)piperazin-1-yl)propyl)benzothiazole
[0017] (1) 2-(3-(4-piperazinaldehyde-1-yl)propyl)benzothiazole
[0018] Add 0.50g (2.36mmol) of 2-(3-chloropropyl)benzothiazole and 0.50g (3.80mmol) of N-formylpiperazine to 10mL of anhydrous dichloromethane, and add sodium triacetoxyborohydride 1.00 g(4.72mmol), stirred at room temperature for 24h, added 20mL ice water, extracted with dichloromethane (3×10mL), dried the organic layer with anhydrous sodium sulfate and purified by column chromatography to obtain 2-(3-( 4-piperazinaldehyde-1-yl)propyl)benzothiazole 0.42g, yield: 61.7%. 1 HNMR(CDCl 3 ,500MHz)δ:7.91(d,J=8.0Hz,1H), 7.83(s,1H), 7.50(d,J=8.0Hz,1H), 7.40(t,J=8.0Hz,1H), 7.32( t,J=8.0Hz,1H), 3.60(t,J=9.4Hz,2H), 3.36(m,J=6.8Hz,2H), 3.16-3.20(m,4H), 2.70-2.75(m4H), 2.26-2.32(m,2H); ESIMSm / z(%)290.4(M+1 + , 100); elemental analysis, measured value (calculated value), %: C62.11 (62.26), H6.69 (6.62), N14.49 (14.52).
[0019] (2) Synthes...
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[0023] Example 2: Synthesis of 2-(3-(4-(4-hydroxybenzyl)piperazin-1-yl)propyl)benzothiazole
[0024] Dissolve 2-(3-(4-piperazin-1-yl)propyl)benzothiazole (0.10g, 0.38mmol) in methanol (10mL), add 70μL (0.65mmol) of p-hydroxybenzaldehyde, acetic acid ( 80μL), sodium cyanoborohydride (0.050g, 0.80mmol), stirred at room temperature for 5 hours, the mixture was extracted with dichloromethane and water, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, the crude product was passed through a Flash column After chromatographic separation, 0.12 g of 2-(3-(4-(4-hydroxybenzyl)piperazin-1-yl)propyl)benzothiazole was obtained with a yield of 85.4%. 1 HNMR(CDCl 3 ,500MHz)δ: 9.32(s,1H),7.92(d,J=7.5Hz,1H),7.50(d,J=9.3Hz,1H),7.43(t,J=6.2Hz,1H),7.40( q, J = 5.0Hz, 2H), 7.32 (t, J = 6.5 Hz, 1H), 7.20 (t, J = 8.0 Hz, 2H), 3.65 (t, J = 9.4 Hz, 2H), 3.35 (s, 2H), 3.26(s,2H),3.12-3.19(m,4H),2.72-2.77(m4H),2.25-2.30(m,2H); ESIMSm / z(%)368.5(M+1 + , 100); el...
Example Embodiment
[0025] Example 3: Synthesis of 2-(3-(4-(4-methylbenzyl)piperazin-1-yl)propyl)benzothiazole
[0026] Dissolve 2-(3-(4-piperazin-1-yl)propyl)benzothiazole (0.10g, 0.38mmol) in methanol (10mL), add 70μL of p-methylbenzaldehyde (0.59mmol), acetic acid (80μL), sodium cyanoborohydride (0.050g, 0.80mmol), stirred at room temperature for 5 hours, extracted the mixture with dichloromethane and water, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, the crude product was subjected to Flash After column chromatography, 0.09 g of 2-(3-(4-(4-methylbenzyl)piperazin-1-yl)propyl)benzothiazole was obtained with a yield of 64.3%. 1 HNMR(CDCl 3 ,500MHz)δ:7.93(d,J=8.0Hz,1H),7.49(d,J=8.0Hz,1H),7.45(t,J=8.5Hz,1H),7.42(q,J=5.5Hz, 2H), 7.30 (t, J = 8.2 Hz, 1H), 7.18 (t, J = 8.6 Hz, 2H), 3.66 (t, J = 8.0 Hz, 2H), 3.32 (s, 2H), 3.25 (m, J = 6.0Hz, 2H), 3.15-3.20 (m, 4H), 2.72-2.75 (m4H), 2.32 (s, 3H), 2.20-2.24 (m, 2H); ESIMSm / z (%) 366.5 (M+ 1 + , 100); el...
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