- Practical preparation of 3-chloro-4-methoxybenzylamine hydrochloride
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The title compound was prepared in a practical manner by chlorinating 4- methoxybenzylamine with sulfuryl chloride in acetic acid in 79-82% yields with little side reaction.
- Endo, Masaki,Douglas, Jim
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Read Online
- Catalytic Reduction of Nitriles by Polymethylhydrosiloxane Using a Phenalenyl-Based Iron(III) Complex
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The reduction of nitriles to primary amines using an inexpensive silane such as polymethylhydrosiloxane (PMHS) is an industrially important reaction. Herein we report the synthesis of an earth-abundant Fe(III) complex bearing a phenalenyl-based ligand that was characterized by mass spectroscopy, elemental analysis, cyclic voltammetry, and single-crystal X-ray diffraction. The complex showed excellent catalytic activity toward reduction of aromatic, heteroaromatic, aliphatic, and sterically crowded nitriles to produce primary amines using polymethylhydrosiloxane (PMHS).
- Das, Shyamal,Das, Hari Sankar,Singh, Bhagat,Haridasan, Rahul Koottanil,Das, Arpan,Mandal, Swadhin K.
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supporting information
p. 11274 - 11278
(2019/09/10)
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- COMPOSITION CONTAINING 3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE, AND METHOD FOR PRODUCING SAME
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There is provided a method for producing, at a high yield, a composition containing 3-chloro-4-methoxybenzylamine hydrochloride (CMBA-HCl) in which the purity of CMBA-HCl is high. This method comprises a chlorination step involving a chlorination reaction that generates CMBA-HCl from 4-methoxybenzylamine hydrochloride using hydrogen peroxide and hydrochloric acid. There is also provided a CMBA-HCl-containing composition which is produced by the aforementioned production method and in which the purity of CMBA-HCl is high.
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Paragraph 0054
(2017/04/11)
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- PROCESS FOR THE PREPARATION OF (S)-4-[(3-CHLORO-4-METHOXYBENZYL)AMINO]-2-[2- (HYDROXYMETHYL)-1-PYRROLIDINYL]-N-(2-PYRIMIDINYL METHYL-5-PYRIMIDINE CARBOXAMIDE
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The present invention relates to an improved process for the preparation of (S)-4-[(3- chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinyl ethyl)- 5-pyrimidine carboxamide compound of formula-1 represented by the following structural formula.
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Page/Page column 21
(2015/01/16)
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- Mono-chlorination of electron-rich arylalkyl- and heteroarylalkyl-amines and amino acids using sulfuryl chloride
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Sulfuryl chloride has been used to mono-chlorinate electron-rich arylalkyl- and heteroarylalkyl-amines and amino acids in a mild and efficient one-pot transformation with straightforward purification. Protection of the amines was not needed, and racemization of the chiral amino acids was minimal.
- Yu, Guixue,Mason, Helen J.,Galdi, Kim,Wu, Ximao,Cornelius, Lyndon,Zhao, Ning,Witkus, Michael,Ewing, William R.,Macor, John E.
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p. 403 - 407
(2007/10/03)
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- Design, synthesis, and evaluation of azepine-based cryptophycin mimetics
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Cryptophycins, depsipeptides isolated from terrestrial blue-green algae, show potent activity against a variety of tumor cell lines. Given the potential of the cryptophycins for cancer therapy, we developed a new class of non-peptide peptidomimetic, designed to replace the 16-membered macrolide ring with a 7-membered azepine ring for attachment of the cryptophycin side chains with the required spatial orientation to mimic the conformation of the relevant region of the natural product. Monte Carlo conformational analysis revealed excellent overlay of the local minimum structural model 6 and X-ray structure of (+)-cryptophycin-3 (5). Starting from this structural model, we designed and synthesized compounds (+)-25, (+)-30, and (+)-34 as potential mimics of cryptophycins. Compounds (+)-25, (+)-30, and (+)-34 were tested for in vitro cytotoxicity against six human cancer cell lines. Although only modest activities were observed, these results suggested that a new series of bioactive cryptophycin analogues might be available by structural modification of the central ring system of the cryptophycins.
- Smith III, Amos B.,Cho, Young Shin,Pettit, G. Robert,Hirschmann, Ralph
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p. 6991 - 7009
(2007/10/03)
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- First generation design, synthesis, and evaluation of azepine-based cryptophycin analogues.
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[structure: see text] Azepine-based cryptophycin mimics (+)-4 and (+)-5 have been designed and synthesized. Biological evaluation revealed modest in vitro activity against several human tumor cell lines, thereby supporting the utility of novel scaffolds for the design and synthesis of cryptophycin analogues.
- Smith 3rd.,Cho,Zawacki,Hirschmann,Pettit
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p. 4063 - 4066
(2007/10/03)
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- 4-Benzylamino-1-chloro-6-substituted phthalazines: Synthesis and inhibitory activity toward phosphodiesterase 5
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We synthesized various 4-benzylamino-1-chloro-6-substituted phthalazines (15) and 4-benzylamino-1-chloro-7-substituted phthalazines (16) and evaluated their inhibitory activity toward phosphodiesterase 5 (PDE5) purified from porcine platelets. The PDE5-inhibitory activities of 15 were greater than those of the isomers (16). The preferred substituent at the 4-position of phthalazine was a (3-chloro-4-methoxybenzyl)amino group, and those at the 6- position were cyano, nitro, and trifluoromethyl groups. Compounds 15a (IC50 = 4.8 nM), 15f (3.5 nM), and 15i (5.3 nM) were more potent inhibitors than E4021 (8.6 nM). Compounds 15a and 15f also showed vasorelaxant activity in isolated porcine coronary arteries precontracted with prostaglandin F(2α) (10-5 M). The EC50 values for vasorelaxant action of 15a, 15f, and E4021 were 150, 160, and 980 nM, respectively. These results show that novel PDE5 inhibitors possessing a potent vasorelaxant effect may exist among phthalazine derivatives.
- Watanabe, Nobuhisa,Kabasawa, Yasuhiro,Takase, Yasutaka,Matsukura, Masayuki,Miyazaki, Kazuki,Ishihara, Hiroki,Kodama, Kohtarou,Adachi, Hideyuki
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p. 3367 - 3372
(2007/10/03)
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