Day: October 26, 2022

On May 7, 2020, Hehn, Joerg P.; Blum, Andreas; Hucke, Oliver; Peters, Stefan published a patent.Name: tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate The title of the patent was Preparation of pyridine-3-sulfonamide derivatives as amine oxidase copper containing 3 (AOC3) inhibitors and pharmaceutical compositions and uses thereof. And the patent contained the following:

The invention relates to new pyridinyl sulfonamide derivatives of the formula I [ring A = azetidin-1-yl, pyrrolidin-1-yl, 3-azabicyclo[3.1.0]hexan-3-yl, or piperidin-4-yl; R1 = H, F, Ci, Br, cyano, OH, or each (un)substituted C1-4-alkyl, C1-4-alkyloxy, (CH2)m-CO2H, (CH2)m-C(O)O-(C1-4-alkyl), (CH2)m-C(O)-heterocyclyl, (CH2)m-C(O)NH2, (CH2)m-C(O)NH-(C1-4-alkyl), (CH2)m-C(O)-N-(C1-4-alkyl)2, C(O)-NH-C3-6-cycloalkyl, C(O)-NH-heterocyclyl, (CH2)m-NH-C(O)(C1-3-alkyl), N-(C1-3-alkyl)-C(O)-(C1-4-alkyl), N-(C1-3-alkyl)-C(O)NH2, NH-C(O)NH-(C1-4-alkyl), heterocyclyl, or Ph; wherein multiple R1 may be identical or different, if n = 2; n = 1 or 2; m = 0, 1, or 2] or salts thereof. The compounds I or salts thereof are selective inhibitors of AOC3 (amine oxidase, copper containing 3; vascular adhesion protein 1) and are useful for the treatment of cancer, NASH (non-alc. steatohepatitis), pulmonary fibrosis, retinopathy, nephropathy, or stroke. Thus, 326 mg trans-3-[(6-chloropyridin-3-yl)sulfonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid methylamide and 216 mg tert-Bu N-[2-(fluoromethylidene)-3-hydroxypropyl]carbamate were dissolved in 1 mL THF and 1 mL DMSO, cooled to 0°, treated with 0.53 mL 2 M sodium tert-butoxide/THF solution, and to give stirred at 0° for 5 min and at room temperature for 35 min to give trans-3-[6-[[2-[[(tert-butoxycarbonyl)amino]methyl]-3-fluoroallyl]oxy]pyridine-3-sulfonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid methylamide trifluoroacetate. The latter precursor (410 mg) was dissolved in 15 mL CH2Cl2, treated with 266μL CF3CO2H, and stirred at room temperature for 2.5 h to give 38% trans-3-[6-[((E)-2-aminomethyl-3-fluoroallyl)oxy]pyridine-3-sulfonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid methylamide trifluoroacetate (II). II showed IC50 of 12, 162, 43,370 nM against AOC3, AOC2, and AOC1, resp. The experimental process involved the reaction of tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate(cas: 1251006-64-0).Name: tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate

The Article related to pyridinesulfonamide preparation aoc3 inhibitor, amine oxidase copper containing 3 aoc3 inhibitor, vascular adhesion protein 1 inhibitor, azetidinylsulfonylpyridine pyrrolidinylsulfonylpyridine preparation aoc3 inhibitor, azabicyclohexanylsulfonylpyridine piperidinylsulfonylpyridine preparation aoc3 inhibitor and other aspects.Name: tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

On October 18, 2019, Lin, Zhiyang; Lan, Yun; Wang, Chuan published an article.Formula: C11H14ClNO The title of the article was Reductive Allylic Defluorinative Cross-Coupling Enabled by Ni/Ti Cooperative Catalysis. And the article contained the following:

Tertiary alkyl chlorides, secondary alkyl chlorides and bromides, and primary alkyl bromides underwent chemoselective defluorinative cross-coupling reactions with α-trifluoromethyl aryl alkenes in the presence of (indenyl)TiCl3, NiBr2, and 3,4,7,8-tetramethyl-1,10-phenanthroline to yield α-substituted aryl difluoroalkenes such as 4-MeOC6H4C(:CF2)CH2R (R = t-Bu, cyclohexyl, n-octyl). Unfunctionalized and ester-functionalized alkyl halides underwent cross-coupling under the reaction conditions, while a variety of functionalized aryl alkenes underwent cross-coupling. Using this method, gem-difluoroalkene analogs of azaperone, haloperidol, and benperidol were prepared The experimental process involved the reaction of 4-(4-Chlorophenyl)piperidin-4-ol(cas: 39512-49-7).Formula: C11H14ClNO

The Article related to alkyl aryl difluoroalkene chemoselective preparation, nickel titanium catalyst reductive defluorinative coupling trifluoromethylalkene chloroalkane bromoalkane, tertiary secondary chloroalkane reductive defluorinative coupling trifluoromethyl aryl alkene, secondary primary bromoalkane reductive defluorinative coupling trifluoromethyl aryl alkene and other aspects.Formula: C11H14ClNO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem