344329-76-6 四氢吡喃-4-甲酰胺

名称和标识

中文名: 四氢吡喃-4-甲酰胺
英文名: Tetrahydro-2H-pyran-4-carboxamide
CAS号: 344329-76-6
分子式: C6H11NO2
分子量: 129.16
中文别名: 4-甲酰胺基吡喃; 3,4,5,6-四氢吡喃-4-甲酰胺; 四氢-2H-吡喃-4-甲酰胺; 4-氨甲酰基四氢吡喃
英文别名: oxane-4-carboxamide; tetrahydro-2H-4-pyrancarboxamide; 4-Carbamoyltetrahydropyran; tetrahydropyran-4-carboxylic acid amide; 2H-3,4,5,6-tetrahydropyran-4-carboxamide; Tetrahydropyran-4-carboxamide; tetrahydro-2H-pyran-4-carboxamide; Tetrahydro-pyran-4-carbonsaeure-amid; 4-Carbamoyltetrahydro-2H-pyran

安全说明

运输信息：常温运输。危险描述：非危险化学品。

用途与制备

化学合成。

化学合成

路线1：

步骤：将四氢-2H-吡喃-4-羧酸甲酯（7g，48.6mmol）和30％氨水（20mL）的混合物在密闭瓶中于室温搅拌18小时，减压除去过量氨，残余物用乙醇结晶。
条件：With ammonia In water at 20℃; for 18 h。
收率：89%。
参考文献：[1] Patent: WO2012/113774, 2012, A1. Location in patent: Page/Page column 41-42 [2] Patent: US2013/324551, 2013, A1. Location in patent: Paragraph 0326; 0327 [3] ChemMedChem, 2015, vol. 10, # 2, p. 276 - 295 [4] Patent: WO2015/62486, 2015, A1. Location in patent: Paragraph 00325 [5] Patent: US2007/111984, 2007, A1. Location in patent: Page/Page column 45 [6] Patent: US2007/191613, 2007, A1. Location in patent: Page/Page column 9 [7] Patent: US2004/224974, 2004, A1. Location in patent: Page 57 [8] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 11, p. 2629 - 2635 [9] Journal of the Chemical Society, 1930, p. 2525,2529 [10] Patent: WO2004/58759, 2004, A1. Location in patent: Page 283-284 [11] Patent: WO2005/20999, 2005, A1. Location in patent: Page/Page column 248 [12] Patent: WO2005/66126, 2005, A1. Location in patent: Page/Page column 88 [13] Patent: WO2007/75468, 2007, A1. Location in patent: Page/Page column 111

路线2：

步骤：向搅拌的氧杂-4-羧酸（800mg，6.15mmol）的氯仿（5mL）溶液中加入三乙胺（1.28mL，9.22mmol）和氯甲酸异丁酯（884μL，7.37mmol），在0℃和氩气下滴加，搅拌2小时后通氨气15分钟，浓缩后用丙-2-醇/氯仿（1：4,25mL）溶解，经水、5％aHCO3（aq）和1M HCl（aq）洗涤，有机相干燥（Na2SO4）后浓缩，DCM研磨纯化。
条件：Stage #1: With triethylamine; isobutyl chloroformate In chloroform at 0℃; for 2 h; Inert atmosphere; Stage #2: With ammonia In chloroform for 0.25 h; Inert atmosphere。
收率：91%。
参考文献：[1] Patent: WO2015/177367, 2015, A1. Location in patent: Page/Page column 71; 72 [2] Patent: US2014/275016, 2014, A1. Location in patent: Paragraph 0254 [3] Patent: US2014/275080, 2014, A1. Location in patent: Paragraph 0358 [4] Journal of the Chemical Society, 1930, p. 2525,2529 [5] Journal of the Chemical Society, 1930, p. 2525,2529 [6] Patent: WO2015/62486, 2015, A1 [7] Patent: CN108003122, 2018, A. Location in patent: Paragraph 0020; 0028; 0034; 0035; 0036; 0044; 0052

路线3：

步骤：在玻璃容器中加入6.30g（38.5mmol）四氢吡喃-4-羧酸氯化物，在20g（329mmol）28重量％氨水中，0℃搅拌反应6小时，过滤干燥得到产物。
条件：With ammonia In water at 0℃; for 6 h。
收率：62%。
参考文献：[1] Patent: US2008/306287, 2008, A1. Location in patent: Page/Page column 6 [2] Journal of the Chemical Society, 1930, p. 2525,2529 [3] Journal of the Chemical Society, 1930, p. 2525,2529

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