- Difluoromethyl Nitrile Oxide (CF2HCNO): A Neglected Chemical Reagent
-
A novel chemical reagent – difluoromethyl nitrile oxide, CF2HCNO – was generated in situ for the first time. The synthesis commenced with ethyl difluoroacetate and included only two chemical steps. The difluoromethyl nitrile oxide smoothly participated in [3+2]-cycloaddition reactions with alkynes and enamines to give CF2H-isoxazoles; these products are promising cores for agrochemistry. A representative CHF2-isoxazole was incorporated into the known fungicide Fluxapyroxad (BASF), and the synthesized analogue showed higher antifungal activity than the parent fungicide.
- Khutorianskyi, Andrii,Chalyk, Bohdan,Borysko, Petro,Kondratiuk, Anna,Mykhailiuk, Pavel K.
-
-
Read Online
- IMIDAZO[1,2-B]PYRIDAZINE IL-17A INHIBITORS
-
The invention provides certain difluorocyclohexyl-imidazopyridazinyl-imidazolidinone compounds of formula II as IL-17A inhibitors, pharmaceutical compositions thereof, and methods of using a compound of formula II to treat certain symptoms of psoriasis, rheumatoid arthritis or multiple sclerosis.
- -
-
Page/Page column 17-18; 42-43
(2020/07/25)
-
- MANUFACTURING METHOD OF α,α-DIFLUORO ACETALDEHYDE
-
PROBLEM TO BE SOLVED: To provide an effective industrial manufacturing method of α,α-difluoro acetaldehydes. SOLUTION: The disclosed manufacturing method of α,α-difluoro acetaldehydes can be achieved by reacting α,α-difluoroacetic acid esters with hydrogen gas (H2) in presence of a ruthenium-catalyst and a base. By employing specific reaction conditions (catalyst, base, pressure or the like), α,α-difluoro acetaldehydes can be manufactured at high conversion rate and high selectivity. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
- -
-
Paragraph 0067-0068; 0069
(2017/09/19)
-
- Difluoroalkylcyclopropyl amino acids and esters, and syntheses thereof
-
The invention provides methods of synthesizing compounds in an asymmetric or enantioenriched fashion, wherein the compounds are useful intermediates in the synthesis of viral protease inhibitors.
- -
-
Page/Page column 34
(2017/11/28)
-
- Preservation method of alpha, alpha-difluoroacetaldehyde alkyl hemiacetal
-
The invention relates to a preservation method of alpha, alpha-difluoroacetaldehyde alkyl hemiacetal, alpha-difluoroacetaldehyde alkyl hemiacetal as shown in the formula and oxygen (O2) or a non-active gas, a gas-phase and liquid-phase gas-liquid state is stored in the closed container the method is characterized, the following steps: adjusting the oxygen concentration of the gas-phase part in the container to be less than 5000 ppm, and then the alpha and alpha are arranged in the container under the light shielding condition; the difluoroacetaldehyde alkyl hemiacetal is stored. In the formula, r1 represents an alkyl group or a substituted alkyl group. According to the method, alpha and alpha can be effectively inhibited for a long time. The method comprises the following steps: converting the difluoroacetaldehyde alkyl hemiacetal to the difluoroacetic acid.
- -
-
Paragraph 0114; 0115
(2017/12/28)
-
- METHOD FOR IMPROVING STORAGE STABILITY OF 2,2-DIFLUOROACETALDEHYDE
-
PROBLEM TO BE SOLVED: To provide a method for improving storage stability of 2,2-difluoroacetaldehyde. SOLUTION: A method for improving storage stability of 2,2-difluoroacetaldehyde, comprising at least the following step 1 and step 2. Step 1: a step of preparing a "2,2-difluoroacetaldehyde-alcohol complex" containing a hemiacetal of 2,2-difluoroacetaldehyde and an excess alcohol. Here, in the "2,2-difluoroacetaldehyde-alcohol complex," a total number of moles of alcohol relative to a total number of moles 2,2-difluoroacetaldehyde is 1.15 to 4.00 moles. Step 2: a step of storing the "2,2-difluoroacetaldehyde-alcohol complex" obtained in the step (1) in a storage container. According to the method, conversion of 2,2-difluoroacetaldehyde to its dimer can be suppressed, and its composition hardly changes over a long period of time while maintaining reactivity inherent to an aldehyde. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
- -
-
Paragraph 0114
(2017/01/12)
-
- Alpha,Alpha-Difluoroacetaldehyde Production Method
-
A production method of α,α-difluoroacetaldehyde according to the present invention includes reaction of an α,α-difluoroacetic acid ester with hydrogen gas (H2) in the presence of a ruthenium catalyst. It is possible to selectively obtain α,α-difluoroacetaldehyde as a partially reduced product of the hydrogenation reaction by the adoption of specific reaction conditions (in particular, reaction solvent and reaction temperature). This hydrogenation process can be alternative to the industrially unpractical hydride reduction process.
- -
-
Paragraph 0081
(2016/01/30)
-
- PYRROLOPYRIMIDINE AND PURINE DERIVATIVES
-
The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein Q, T, V, W, X, Y, Z, ring A, R1, R2, R3, R4, R5, R5a, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and m are defined herein. There novel pyrrolopyrimidine and purine derivatives are useful in the treatment of abnormal cell growth, such as cancer, in mammals. Additional embodiments relate to pharmaceutical compositions containing the compounds and to methods of using the compounds and compositions in the treatment of abnormal cell growth in mammals.
- -
-
Paragraph 0986; 0987
(2013/04/10)
-
- The asymmetric synthesis of CF3- or -CF2-substituted tetrahydroquinolines by employing a chiral phosphoric acid as catalyst
-
CF3- or -CF2-containing tetrahydroquinolines have been asymmetrically synthesized from the reaction of fluorinated N-arylimines with benzyl N-vinylcarbamate in the presence of a chiral phosphoric acid.
- Lin, Jin-Hong,Zong, Guoqiang,Du, Ruo-Bing,Xiao, Ji-Chang,Liu, Shubin
-
supporting information; experimental part
p. 7738 - 7740
(2012/09/07)
-
- Highly diastereo- and enantioselective vinylogous Mannich reactions of fluorinated aldimines with siloxyfurans
-
A highly regio- and enantioselective asymmetric vinylogous Mannich reaction of readily available fluorinated aldimines bearing a chiral auxiliary [(S)-1-phenylethyl group] with siloxyfurans to afford chiral fluorine-containing γ-butenolide or γ-lactone derivatives has been developed in the presence of silver acetate (10 mol%) and axially chiral phosphine-oxazoline ligand L1 (11 mol%). In most cases, the corresponding fluorinated adducts were obtained in high yields, good to excellent enantiomeric excesses and up to > 20:1 dr.
- Zhao, Qian-Yi,Yuan, Zhi-Liang,Shia, Min
-
supporting information; experimental part
p. 637 - 643
(2011/04/25)
-
- The asymmetric Friedel-Crafts reaction of indoles with fluoroalkylated nitroalkenes catalyzed by chiral phosphoric acid
-
The enantioselective Friedel-Crafts fluoroalkylation of indoles with fluoroalkylated nitroalkenes, catalyzed by chiral phosphoric acid is described. The regioselectivity of fluoroalkylated nitroalkenes is a problem worth discussing, and it was found that the carbon atom adjacent to the fluoroalkyl group is more reactive than that adjacent to NO2 group.
- Lin, Jin-Hong,Xiao, Ji-Chang
-
experimental part
p. 4536 - 4539
(2011/10/09)
-
- Facile preparation of polyfluoroalkylated aldimines from polyfluoroalkanoic acids
-
Polyfluoroalkylated aldimines were prepared by reducing polyfluoroalkyl imidoyl chlorides, which are readily available from polyfluoroalkanoic acids, with LTBA (lithium tri-tert-butoxyaluminum hydride). Georg Thieme Verlag Stuttgart.
- Takagi, Jun,Takihana, Ryozo,Kuwano, Akiko,Uneyama, Kenji
-
p. 1624 - 1628
(2008/02/05)
-
- PYRIDYL AND PHENYL SUBSTITUTED PIPERAZINE-PIPERIDINES WITH CXCR3 ANTAGONIST ACTIVITY
-
The present application discloses a compound, or enantiomers, stereoisomers, rotamers, tautomers, racemates or prodrug of said compound, or pharmaceutically acceptable salts, solvates or esters of said compound, or of said prodrug, said compound having the general structure shown in Formula 1: and the pharmaceutically acceptable salts, solvates and esters thereof. Also disclosed is a method of treating chemokine mediated diseases, such as, palliative therapy, curative therapy, prophylactic therapy of certain diseases and conditions such as inflammatory diseases (non limiting example(s) include, psoriasis), autoimmune diseases (non limiting example(s) include, rheumatoid arthritis, multiple sclerosis), graft rejection (non limiting example(s) include, allograft rejection, xenograft rejection), infectious diseases (e.g , tuberculoid leprosy), fixed drug eruptions, cutaneous delayed-type hypersensitivity responses, ophthalmic inflammation, type I diabetes, viral meningitis and tumors using a compound of Formula 1.
- -
-
Page/Page column 141-142
(2008/06/13)
-
- Difluoridnated Carbaacyclonucleosides: Synthesis and Evaluation of Antiviral Activity
-
The synthesis of 4-benzoyloxy-5,5-difluoropentan-1-ol from ethyl difluoroacetate is described. Condensation with pyrimidine bases gave carbaacyclonucleosides. The uracil (8d), cytosine (9) and thymine (10c) congeners were evaluated, and found inactive, in a large variety of antiviral assays.
- Lewis, Maureen,Clercq, Erik De
-
p. 844 - 856
(2007/10/03)
-
- Diastereoselective Synthesis of the Nonracemic Methyl syn-(3-Fluoroalkyl)isoserinates
-
Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (RF = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%) However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.
- Abouabdellah, Ahmed,Bégué, Jean-Pierre,Bonnet-Delpon, Danièle,Nga, Truong Thi Thanh
-
p. 8826 - 8833
(2007/10/03)
-
- A Remarkably Simple Route to Versatile Difluoromethylated Molecules
-
Difluoroacetaldehyde ethyl hemiacetal (1), prepared from ethyl difluoroacetate and lithium aluminum hydride in diethyl ether, was found to be a potential difluoroethylating reagent for the preparation of a wide variety of difluoromethylated compounds.Compound 1 shows promise for use in the synthesis of carbinols prepared by the reaction of 1 with metal reagents or enol silyl ethers, the synthesis of amino acid ketones and β-lactams via the nucleophilic reaction of imines, and the synthesis of sugar analogues.
- Kaneko, Sadanori,Yamazaki, Takashi,Kitazume, Tomoya
-
p. 2302 - 2312
(2007/10/02)
-