Pyrimidine substituted benzenepropanoic acid derivative, its preparation method and use in curing polycystic kidney disease
A technology of compounds and mixtures, applied in the field of pyrimidine-substituted phenylpropionic acid derivatives, which can solve the problems of aggravating side effects of heart failure
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Embodiment 1
[0153] 2-Ethoxy-3-{4-[2-amino-4-oxo-6-(1-benzylpiperazinyl)]pyrimidinyl}phenylpropionic acid
[0154] 2-Ethoxy-2-(diethoxyphosphoryl)-ethyl acetate was added to a mixed solution of methyl tert-butyl ether (55 mL) and tert-butyl potassium (4.65 g) under nitrogen protection, Add p-benzyloxybenzaldehyde (4.61g) to the mixture at 5°C, then add tert-butanol (6.70g), react at 15°C for about 30min, TLC detects that the reaction is complete, add water (30mL) , rotary evaporated the organic phase, added ethanol (30mL), recrystallized, washed with ethanol / water (1:1 v / v), dried to obtain 2-ethoxy-1-(4-benzyl)phenylacrylic acid ethyl Esters, 92% yield.
[0155] 1 HNMR, 400MHz (acetone-d6): δ1.12(t, J=7Hz), 1.32(t, J=7Hz), 1.33(t, J=7Hz), 3.91(q, J=7Hz), 4.12(q , J=7Hz), 4.24(q, J=7Hz), 5.12(s), 5.17(s), 6.10(s), 6.93(s), 6.94(d, J=9Hz), 7.05(d, J= 9Hz), 7.15(d, J=9Hz), 7.32~7.42(m), 7.46~7.50(m), 7.81(d, J=9Hz).
[0156] Dissolve ethyl 2-ethoxy-1-(4-benzyl)phenylacrylate (20.0g) in ...
Embodiment 2
[0161] 2-Methyl-2-phenoxy-3-{4-[2-amino-4-oxo-6-(1-benzyl)piperazinyl]pyrimidinyl}phenylpropanoic acid
[0162] Dissolve ethyl 2-phenoxypropionate (15g) in anhydrous THF, add lithium diisopropylamide (26ml) at -78°C, stir for half an hour, add p-benzyloxybenzaldehyde ( 10 g), stirred overnight under nitrogen protection. Add NH at room temperature 4 Cl saturated liquid until there are no bubbles, the aqueous layer is extracted twice with ethyl acetate, the organic phases are combined, rotary evaporated, passed through the column, PE:EA=10:1 to 4:1, and the light yellow solid 2-methyl-2 -Ethyl phenoxy-3-hydroxy-3-(4-benzyloxy)phenylpropanoate, 50% yield. Under ice-cooling, add 2-methyl-2-phenoxy-3-hydroxyl-3-(4-benzyloxy)phenylpropionic acid ethyl ester (10g) and dichloromethane into the three-necked flask, Slowly drive the barrel into the BF 3 -Et 2 O(3.06ml) and (C 2 h 5 ) 3 SiH (4.08ml), into a blood-red liquid, overnight, with saturated NaCO 3 The liquid was neutral...
Embodiment 3
[0169] 2-Methyl-2-phenoxy-3-{4-{2-amino-4-oxo-6-[1-(3,4-formalyl)benzyl]piperazinyl}pyrimidine phenylpropionic acid
[0170] With 2-amino-4-chloro-6-[1-(3,4-formyl) benzylpiperazinyl] pyrimidine replaces 2-amino-4-chloro-6-( 1-benzyl)piperazinylpyrimidine was prepared according to the preparation method described in Example 2.
[0171] 1 HNMR (300MHz, CD 3OD): δ1.40(s, 3H), 3.00(t, 4H), 3.20(q, 2H), 3.70(t, 4H), 4.05(s, 2H), 5.19(s, 1H), δ5.90 (d, 2H), 6.88-7.06 (m., 5H), 7.20-7.37 (m, 4H), 7.46-7.55 (m, 3H).
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