- Deprotection of N-Boc Groups under Continuous-Flow High-Temperature Conditions
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The scope of thermolytic, N-Boc deprotection was studied on 26 compounds from the Pfizer compound library, representing a diverse set of structural moieties. Among these compounds, 12 substrates resulted in clean (≥95% product) deprotection, and an additional three compounds gave ≥90% product. The thermal de-Boc conditions were found to be compatible with a large number of functional groups. A combination of computational modeling, statistical analysis, and kinetic model fitting was used to support an initial, slow, and concerted proton transfer with release of isobutylene, followed by a rapid decarboxylation. A strong correlation was found to exist between the electrophilicity of the N-Boc carbonyl group and the reaction rate.
- Li, Bryan,Li, Ruizhi,Dorff, Peter,McWilliams, J. Christopher,Guinn, Robert M.,Guinness, Steven M.,Han, Lu,Wang, Ke,Yu, Shu
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p. 4846 - 4855
(2019/01/30)
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- A kind of 3,4-dichloro-thiazole derivatives and process for their preparation and use
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The invention provides 3,4-dichloro isothiazole derivatives, their preparation method and application. The invention relates to a heterocyclic compound containing 3,4-dichloro isothiazol, and the compound is represented by the following chemical structural general formula. The invention discloses the structural general formula of the compound, a synthetic method of the compound and applications of the compound as pesticide, bactericide, anti-plant virus agent, and plant activator, and a technology of mixing the compound with agriculturally acceptable auxiliary agents or synergists for preparing pesticide, bactericide, anti-plant virus agent, and plant activator. The invention further discloses the combined application of the compound and the commercial pesticide, bactericide, anti-plant virus agent, and plant activator in controlling diseases, insect pests, and virus diseases in agriculture, forestry and gardening, and a preparation method of the compound and the commercial pesticide, bactericide, anti-plant virus agent, and plant activator.
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Paragraph 0036-0039; 0091-0092
(2016/10/08)
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- Synthetic method of Dasatinib intermediate
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The invention discloses a synthetic method of a Dasatinib intermediate. The method comprises the steps that compound 3-alkoxy acrylate shown in formula I, urea and potassium sulphide are subjected to contact reaction under the catalysis of nanometer copper powder to obtain Dasatinib intermediate 2-amino-thiazole-5-formate, wherein R1 and R2 are methyl, ethyl or propyl independently. According to the method for preparing the Dasatinib intermediate, the conditions are mild, the yield is effectively improved, pollution caused by bromine treatment to environment is reduced, and meanwhile the production cost is reduced due to the fact that cheap raw material urea is adopted.
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Paragraph 0034; 0035
(2017/02/02)
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- HETEROCYCLIC AMINO BERBAMINE DERIVATIVES, PREPARATION METHOD AND USE THEREOF
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The present invention relates to a novel berbamine derivative of formula I or a pharmaceutically acceptable salt thereof, a process for preparation of the same, a pharmaceutical composition comprising said compound and its use in manufacture of an antitumor medicament.
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Paragraph 0095; 0096
(2013/07/25)
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- The synthesis of 3-pyrazinyl-imidazo[1,2-a]pyridines from a vinyl ether
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A new method has been developed for the synthesis of 3-pyrazinyl-imidazo[1, 2-a]pyridines. 2-Chloro-6-[(Z)-2-ethoxyethenyl]pyrazine was treated with N-bromosuccinimide in dioxane-water to generate the 2-bromo-2-(6-chloropyrazin- 2-yl)-1-ethoxyethanol intermediate. In a subsequent one-pot step, optional treatment with various 2-aminopyridines provided the cyclized 3-pyrazinyl-imidazo[1,2-a]pyridines in 31-76% yields.
- Collins, Michael Raymond,Huang, Qinhua,Ornelas, Martha A.,Scales, Stephanie A.
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scheme or table
p. 3528 - 3530
(2010/08/22)
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- A new and efficient preparation of 2-aminothiazole-5-carbamides: Applications to the synthesis of the anti-cancer drug dasatinib
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A new and efficient method has been developed for the synthesis of 2-amino-N-(-(2-chloro-6-methylphenyl)-thiazole-5-carboxamide. The new method involves a chemoselective α-bromination of β-ethoxyacrylamide followed by a one-pot treatment with thiourea to give the desired 2-aminothiazole-5-carboxylamide in excellent yield. Application of this new method to the efficient synthesis of the anti-cancer drug dasatinib was demonstrated.
- Chen, Bang-Chi,Zhao, Rulin,Wang, Bei,Droghini, Roberto,Lajeunesse, Jean,Sirard, Pierre,Endo, Masaki,Balasubramanian, Balu,Barrisha, Joel C.
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scheme or table
p. 32 - 38
(2010/09/05)
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- IMIDAZOLE AND THIAZOLE DERIVATIVES AS ANTIVIRAL AGENTS
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The present invention relates to compounds of the formula (I), wherein R1, R2, A, B, D, E, F, G and Ar are as defined herein, and pharmaceutically acceptable salts thereof, useful in the prevention and treatment of hepatitis C infections.
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Page/Page column 20-21
(2010/02/15)
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- OPIOID RECEPTOR ANTAGONISTS
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A compound of the formula I: (I) wherein the variables are as described herein, or a pharmaceutically acceptable salt, solvate, enantiomer, racemate, diastereomer or mixture thereof, formulations and methods of use thereof are disclosed.
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Page 26; 46-47
(2010/02/08)
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- N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B Antagonists
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Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are effective as NMDA NR2B antagonists useful for relieving pain.
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- A new facile synthesis of 2-aminothiazole-5-carboxylates
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A new facile method has been developed for the synthesis of 2-aminothiazole-5-carboxylates. The new method involves reaction of ethyl β-ethoxyacrylate with N-bromosuccinimide (NBS) to give a novel intermediate, α-bromo-α-formylacetate hemiacetal. Cyclization of the in situ formed hemiacetal with thioureas afforded 2-aminothiazole-5-carboxylates in 60-98% yields.
- Zhao, Rulin,Gove, Stacey,Sundeen, Joseph E.,Chen, Bang-Chi
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p. 2101 - 2102
(2007/10/03)
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- Pharmaceutical composition for inhibiting HIV protease
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A pharmaceutical composition is disclosed which comprises a solution of an HIV protease inhibiting compound in a pharmaceutically acceptable organic solvent comprising a mixture of (1) (a) a solvent selected from propylene glycol and polyethylene glycol or (b) a solvent selected from polyoxyethyleneglycerol triricinoleate, polyethylene glycol 40 hydrogenated castor oil, fractionated coconut oil, polyoxyethylene (20) sorbitan monooleate and 2-(2-ethoxyethoxy)ethanol or (c) a mixture thereof and (2) ethanol or propylene glycol.
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- Pharmaceutical composition
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A solid pharmaceutical composition is disclosed which comprises a pharmaceutically acceptable adsorbent or a mixture of pharmaceutically acceptable adsorbents to which is adsorbed a mixture of (1) a pharmaceutically acceptable organic solvent or a mixture of pharmaceutically acceptable organic solvents, (2) an HIV protease inhibiting compound and (3) one or more pharmaceutically acceptable acids. The solid composition can optionally be encapsulated in a hard gelatin capsule.
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- Pseudohalogen chemistry. XI. Some aspects of the chemistry of octhiocyanato-β-dicarbonyl compounds
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Enolised α-thiocyanato-β-dicarbonyl compounds dimerise in ethanol at room temperature to give tautomeric 4,5-disubstituted 2-amino- and 2-acetamido-thiazoles by a C-S-C + C-N cyclisation. Tautomerism is due to the unusual 4-(β-dicarbonyl-α-thio) substituent. Competing intramolecular cyclisations lead to minor amounts of heterocycles containing the thiazole and/or oxathiole ring systems.
- Atkins, Elaine F.,Dabbs, Steven,Guy, Robert G.,Mahomed, Akbar A.,Mountford, Philip
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p. 7253 - 7264
(2007/10/02)
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- SYNTHESIS OF TWO NEW THIAZOLE-CONTAINING OLIGOPEPTIDES AS POTENTIAL DNA MINOR GROOVE BINDING ANALOGS OF NETROPSIN
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On the basis of previous studies on synthetic models related to the antibiotic agents Netropsin and Distamycin-A, the design and synthesis of two potential DNA minor groove ligands are described.Methia-Nt and Isothia-Nt were prepared by liquid-phase peptidic synthesis from the key compounds ethyl 2-amino-5-methylthiazole-4-carboxaldehyde (1) and ethyl 2-aminothiazole-5-carboxylate (8) respectively.
- Plouvier, Bertrand,Bailly, Christian,Houssin, Raymond,Henichart, Jean-Pierre
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p. 693 - 701
(2007/10/02)
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