In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 632365-54-9 as follows. Recommanded Product: 632365-54-9
To a refluxing mixture of 7.0 g (175 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) and 10.45 g (88.5 mmol) [OF DIETHYL CARBO7LATE (CO (OETJ2)] in 100 mL of toluene was added dropwise via an addition funnel a mixture of 10 g [(44. 3] mmol) [OF 1- (4-BENZYLOXY-] [PHENYL)-ETHANO7LE] in 20 mL of toluene, and the resulting mixture was heated at reflux under argon for 1 h. The reaction mixture was then cooled to [0C,] quenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate formed, and it dissolved upon subsequent addition of water. The separated organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (10% hexane in dichloromethane) to afford 9.2 g (70% yield) of desired [3-(4-BENZYLOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER] as indicated by 1H NMR. To a solution of 2 g (6.7 mmol) of 3-(4-benzyloxy-pyenyl)-3-oxo-propionic acid ethyl ester in 12 mL of ethanol (heated slightly for complete dissolution) was added dropwise 7 mL (7 mmol) [OF POTASSIUFN T-BUTOXIDE (KOTBU 1 MSOLUTION IN T-BUTANOL),] during which time a precipitate formed. The reaction mixture was stirred at rt for 20 min, then diethyl ether was added and the precipitate was collected by filtration, washed with ether and dried to afford 2.2 g (98% yield) of desired [3-(4-BENZYLOXY-PHE7LYL)-3-OXO-PROPIONIC ACID ETHYL ESTER POTASSIUM] salt as indicated by 1H NMR. A mixture 100 mg (0.3 mmol) of 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester potassium salt, 86 mg (0.45 mmol) of 2-cyclohexylethyl bromide, and 17 mg (0.1 mmol) of potassium iodide (KI) in 1 mL [OF DIMETHYLFONNAMIDE (DMF)] in a 4 mL vial was shaken in a sand bath at [80 C] overnight. The mixture was then concentrated to give a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) 85 mg (70% yield) of 2- (4-benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl ester as a solid as indicated by LC-MS-calcd for [C26H3202 [M++H] +] : 409.23, found: 409.2. A mixture of 71 mg (0.171 mmol) [OF 2-(4-BENZYLOXY-BE7LZOYL)-4-CYCLOHEXYL-BUTYRIC ACID] ethyl ester, 24 mg (0.171 mmol) of [5-AMINO-1H-PYRAZOLE-3-CARBOXYLIC ACID METHYL ESTER,] 7 mg (20 [MOL%)] [OF P-TOLUEYLESULFOFZIC ACID MONOHYDRATE (PTSA),] and 3 mL of chlorobenzene was heated at [120 C] overnight. The reaction mixture was then concentrated to a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) desired 5-(4-benzyloxy-phenyl)-6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester as a solid as indicated by LC-MS-calcd for [C29H3LN304] [[M +H] +] : 486.23, found: 486.2. This material was then converted to 5-(4-benzyloxy-phenyl)- 6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (559) via the well known LiOH saponification protocol (10% yield over 2 steps); LC-MS-calcd for [C2SH29N304] [[M++H] +] : 472.22, found: 472.2. Note that the same synthetic sequence was carried out from the commercially available [3-FURAN-3-YL-3-OXO-PROPIONIC ACID ETHYL ESTER] as depicted above to give [6- (2-CYCLOHEXYL-ETHYL)-] 5-furan-3-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (612).
According to the analysis of related databases, 632365-54-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; NEOGENESIS PHARMACEUTICALS, INC.; WO2003/101993; (2003); A1;,
Pyrazole – Wikipedia,
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