{"id":5074,"date":"2021-07-01T03:36:31","date_gmt":"2021-06-30T19:36:31","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=5074"},"modified":"2021-07-01T03:36:31","modified_gmt":"2021-06-30T19:36:31","slug":"new-learning-discoveries-about-ethyl-5-amino-1h-pyrazole-4-carboxylate-2","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=5074","title":{"rendered":"New learning discoveries about Ethyl 5-amino-1H-pyrazole-4-carboxylate"},"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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 5-amino-1H-pyrazole-4-carboxylate<\/a><\/p>\n

A mixture of ethyl 5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrim idine-3-carboxylate (major isomer) and ethyl 8-methyl-6, 7-dihydro-5H-cyclopenta[d]pyrazolo[1 ?5-a]pyrimidine-3-carboxylate (minor isomer) (1 .28 g, 5.22 mmol, ratio of isomers ca 85\/15) was stirred in a mixture of lithium hydroxide (26 ml, 26 mmol, 1 M aqueous solution), tetrahydrofuran (43 ml) and methanol (9.1 ml) for 3 days at room temperature. For work-up, aqueous hydrochloric acid (2 M) was added and the precipitate formed was collected byfiltration, washed with water and dried to yield the title compounds as mixture of isomers (ca10:1) (770 mg, 68percent).Maior isomer:[C-MS (Method 1): R = 0.71 mm; MS (ESIpos) m\/z = 218.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 12.83-11.51 (br. s, 1H), 8.48 (5, 1H), 3.03 (t, 2H),2.55 (5, 3H), 2.30-2.21 (m, 2H).Minor isomer (characteristic sicinals ciiven):1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 8.45 (5, 1H), 3.00-2.95 (m, 2H), 2.68 (5, 3H), 2.20-2.10 (m, 2H). (benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (172 mg, 0.331 mmol)was added to a mixture of 5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrim idine-3-carboxylic acid (major isomer) and 8-methyl-6, 7-dihydro-5H-cyclopenta[d]pyrazolo[1 ?5- a]pyrimidine-3-carboxylic acid (minor isomer) (60.0 mg, 0.276 mmol, ratio of isomers: 10\/1), trans-4-am ino-N-(2-chloro-4-f luorophenyl)cyclohexanecarboxam ide hydrochloride (76.4 mg, 0.249 mmol) and 192 hI (1.11 mmol) N-ethyl-N-isopropylpropan-2-amine in 2.0 ml N,N10 dimethylformamide and the mixture was stirred over night at room temperature. For work-up,water was added and the precipitate was collected by filtration, washed with water and dried under vacuum at 500 to provide the title compound (103 mg) together with its isomer N{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}-8-methyl-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1 ,5-a]pyrimidine-3-carboxamide (ratios of isomers ca. 10\/1 by 1 HNMR). The two isomers were separated by preparative HPLC [Instrument: Labomatic PumpeHD-5000, Labomatic SP-3000, Labocord 5000, Labomatic Labcol Vario 4000, Gilson GX241; Colum: Chiralpak IE Slim 250×30 mm Nr.027; Solvent: ethanol \/ methanol \/ diethylamine 50:50:0.1 (v\/v\/v), flow: 30 mI\/mm; temperature: room temperature; MWD 254 nm] to give N-{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}-5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrimidine-3-carboxamide (76.0 mg, 57percent yield). The minor isomer was not isolated in pure form.LC-MS (Method 2): R = 1 .23 mm; MS (ESIpos) m\/z = 470.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.51 (br. s, 1H), 8.47 (5, 1H), 8.05 (d, 1H), 7.62(dd, 1H), 7.51 (dd, 1H), 7.23 (td, 1H), 3.87-3.72 (m, 1H), 3.40-3.36 (m, 2H), 3.07-3.01 (m,2H), 2.60 (5, 3H), 2.32-2.22 (m, 2H), 2.15-2.06 (m, 2H), 2.02-1.93 (m, 2H), 1.68-1.50 (m,2H), 1.47-1.32 (m, 2H).<\/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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016\/177658; (2016); 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":[213,131],"tags":[126],"class_list":["post-5074","post","type-post","status-publish","format-standard","hentry","category-1260243-04-6","category-pyrazoles-derivatives","tag-m-w100-200"],"yoast_head":"\nNew learning discoveries about<\/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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