Compound for treating peptic ulcer and preparation method and application thereof
A compound and chemical structural formula technology, applied in the field of medicine, can solve problems such as poor water solubility of fumaric acid vonoprazan
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Embodiment 1
[0029] Example 1 Synthesis of 5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde (compound IV)
[0030]
[0031] At room temperature, add 30 g of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (compound II), 100 ml of acetonitrile (CHCN), 29 g of N,N-diisopropylethyl Amine (DIEA) and 4g of 4-dimethylaminopyridine (DMAP), add 35g of pyridine-3-sulfonyl chloride (compound III) at room temperature, stir and react at room temperature for 30min, after the reaction is complete, add water to quench the reaction, use Adjust the pH to 5 with hydrochloric acid, cool down to room temperature, stir and crystallize, filter, and dry under reduced pressure to obtain compound (IV), which is 44 g of yellow powder with a yield of 84%.
[0032] 1H-NMR (CDCl 3 )δ: 9.90 (1H, s), 8.81 (1H, dd, J = 1.4, 4.8Hz), 8.59 (1H, d, J = 2.2Hz), 8.15 (1H, d, J = 1.8Hz), 7.71 ( 1H,dt,J=1.9,8.2Hz), 7.45(1H,m), 7.37(1H,dd,J=4.9,8.1Hz), 7.16(2H,m), δ7.01(1H,t,J= 8.9Hz), 6.67 (1H,d,J=1.7Hz). ...
Embodiment 2
[0033] Example 2 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-propylene glycol methylamine monofumaric acid (compound Ⅰ) synthesis
[0034]
[0035] (1) At room temperature, add 43g of compound (IV) and 200ml of methanol to the reaction flask, add 15g of 3-amino-1,2-propanediol, stir for 0.5h, then add 2g of sodium borohydride in N, N-dimethylacetamide solution, stirred and reacted at room temperature for 0.5h, then added 350ml of water, adjusted the pH to 5 with hydrochloric acid, quenched the reaction, then adjusted the pH to 10 with ammonia water, added 450ml of ethyl acetate for extraction, and the organic phase was extracted with water Wash and concentrate under reduced pressure to obtain the free oily state, which is 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-propylene glycol methylamine mono Free state of fumaric acid (compound V);
[0036] (2) Add 200ml of N,N-dimethylacetamide to compound V, stir to dissolve, add 14g of fum...
experiment example 1
[0044] Experimental Example 1 Water Solubility Evaluation
[0045] Sample: the compound shown in formula I and vonoprazan fumarate;
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