{"id":5375,"date":"2021-07-16T03:27:16","date_gmt":"2021-07-15T19:27:16","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=5375"},"modified":"2021-07-16T03:27:16","modified_gmt":"2021-07-15T19:27:16","slug":"a-new-synthetic-route-of-c5h7n3o2","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=5375","title":{"rendered":"A new synthetic route of C5H7N3O2"},"content":{"rendered":"

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C5H7N3O2<\/a><\/p>\n

To an ice cold suspension of 0.92 g (23 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) (previously washed with hexane and dried under vacuum) in 25 mL of 1,2- dimethoxyethane (DME) was added 0.9 g (5.76 mmol) of [METHYL CYCLOHEXYLACETATE,] and the resulting mixture was stirred at [0 C] for 20 min. Then 1.2 g (8.56 mmol) [OF ETHYL 2-FUROATE] was added, and the reaction mixture was heated at reflux overnight. The mixture was then cooled to [0C,] quenched by the addition of 1 M [HC1] solution to pH=3, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to give a brown oil which was chromatographed on silica gel [(BIOTAGE ;] 10% hexane in dichloromethane) to afford 1.1 g (76% yield) of desired 2-cyclohexyl-3-furan-2-yl-3- [OXO-PROPIONIC ACID METHYL ESTER] as indicated by 1H NMR. A mixture of 1.1 g (4.4 mmol) [OF 2-CYCLOHEXYL-3-FURAN-2-YL-3-OXO-P7 OPIONIC ACID] [METHYL ESTER,] 0.592 g (4.2 mmol) of 5-amino-1H-pyrazole-3-carboxylic acid methyl ester, 76 mg (0.4 mmol, 10 mol%) of p-toluenesulfonic acid monohydrate (PTSA), and 50 mL of chlorobenzene was heated at 120 [C] overnight. The reaction mixture was then concentrated to a residue which was chromatographed on silica gel (7% methanol in dichloromethane) to afford 0.46 g (32% yield) of desired 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro- pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester as indicated [BY IH] NMR; LC-MS- calcd for [C18HL9N304] [[M++H] +] : 342.14, found: 342.3. Conversion of 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester to 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5- [AJPYYIMIDINE-2-CARBOXYLIC ACID] (595) was accomplished via the well known LiOH saponification protocol where the yield was 77%. [LC-MS-CALCD] for [CI7HI7N304] [M++H]+: 328.13, found : 328. 1. 1H NMR [(DMSO-D6)] [8] 8.06-8. 05 (d, J= 2 Hz, 1H), 6.99-6. 98 (d, J= 3.6 Hz, 1H), 6.80-6. 78 (d [OF D,] J= 3.6 Hz, J= 2 Hz, [1H),] 6.39 (s, [1H),] 2.79-2. 71 [(M,] 1H), 2.25-2. 16 [(M,] 2H), 1.77-1. 75 [(M,] [2H),] 1.66-1. 65 [(M,] 1H), 1.59-1. 55 [(M,] 2H), 1.25-1. 20 [(M,] 3H). Note that the same synthetic scheme was carried out for [3-FLUORO-BENZOIC ACID METHYL] ester as depicted above to afford [6-CYCLOHEXYL-5-(3-FLUORO-PHENYL)-7-OXO-4, 7-DISLYDRO-] pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (598); the cyclization yield was slightly improved (54%).<\/p>\n

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.<\/p>\n

Reference:
Patent; NEOGENESIS PHARMACEUTICALS, INC.; WO2003\/101993; (2003); A1;<\/a>,
Pyrazole – Wikipedia<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/p>\n","protected":false},"excerpt":{"rendered":"

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[303,131],"tags":[126],"class_list":["post-5375","post","type-post","status-publish","format-standard","hentry","category-632365-54-9","category-pyrazoles-derivatives","tag-m-w100-200"],"yoast_head":"\nA new synthetic route of<\/title>\n<meta name=\"description\" content=\"Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. 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