{"id":5720,"date":"2021-08-05T03:16:12","date_gmt":"2021-08-04T19:16:12","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=5720"},"modified":"2021-08-05T03:16:12","modified_gmt":"2021-08-04T19:16:12","slug":"the-origin-of-a-common-compound-about-42098-25-9","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=5720","title":{"rendered":"The origin of a common compound about 42098-25-9"},"content":{"rendered":"

Some common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H4ClN3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 5-Chloro-1-methyl-4-nitro-1H-pyrazole<\/a><\/p>\n

Intermediate 43 RRN No.580,582N-(1-(4-Amino-1-methyl-1H-pyrazol-5-yl)-5-hydroxyazepan-4-yl)-2,2,2-trifluoroacetamide A solution of benzyl 4-hydroxy-5-(2,2,2-trifluoroacetamido)azepane-1-carboxylate (935 mg, 3.0 mmol) in MeOH (100 mL) was passed through the H-Cube (full H2, 50 C., flow rate: 1 mL\/min, 30 mm 10% Pd\/C cartridge). The solvent was removed under reduced pressure to give 4-hydroxy-5-(2,2,2-trifluoroacetamido)azepane as a pale yellow solid (514 mg). To a solution of this (500 mg, 2.21 mmol) in dry DMSO (10 mL) was added 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol) and potassium fluoride (513 mg, 8.85 mmol). The reaction mixture was heated at 65 C. for 16 hr. The mixture was poured into water (200 mL) and extracted with EtOAc (5\u00d750 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (70% EtOAc\/isohexane) gave 2,2,2-trifluoro-N-(5-hydroxy-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide as a yellow solid (640 mg). A portion of this solid (200 mg, 0.57 mmol) was dissolved in MeOH (25 mL) and passed through the H-Cube (full H2, 50 C., flow rate: 1 mL\/min, 30 mm 10% Pd\/C cartridge). The solvent was removed under reduced pressure to give N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-hydroxyazepan-4-yl)-2,2,2-trifluoroacetamide as an orange foam (172 mg, 68% over 3 steps). 1H NMR (400 MHz, DMSO) delta 9.22 (d, J=8.1 Hz, 1H), 6.83 (s, 1H), 4.84 (d, J=5.0 Hz, 1H), 3.91-3.73 (m, 2H), 3.32 (s, 3H), 3.28-2.96 (m, 4H), 2.00-1.75 (m, 4H). Exchangeable NH2 not observed.<\/p>\n

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42098-25-9, its application will become more common.<\/p>\n

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013\/79321; (2013); A1;<\/a>,
Pyrazole – Wikipedia<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/p>\n","protected":false},"excerpt":{"rendered":"

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42098-25-9, its application will become more common.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[256,131],"tags":[126],"class_list":["post-5720","post","type-post","status-publish","format-standard","hentry","category-42098-25-9","category-pyrazoles-derivatives","tag-m-w100-200"],"yoast_head":"\nThe origin of a common compound about<\/title>\n<meta name=\"description\" content=\"Some common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H4ClN3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 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