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Chemical Structure| 127561-18-6 Chemical Structure| 127561-18-6

Structure of 127561-18-6

Chemical Structure| 127561-18-6

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Product Details of [ 127561-18-6 ]

CAS No. :127561-18-6
Formula : C10H12F3N3
M.W : 231.22
SMILES Code : FC(F)(F)C1=CC=CC(=N1)N1CCNCC1
MDL No. :MFCD00114706

Safety of [ 127561-18-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 127561-18-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 127561-18-6 ]

[ 127561-18-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 79-04-9 ]
  • [ 127561-18-6 ]
  • 2-chloro-1-[4-(6-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-ethanone [ No CAS ]
  • 2
  • [ 110-85-0 ]
  • [ 39890-95-4 ]
  • [ 127561-18-6 ]
YieldReaction ConditionsOperation in experiment
81.4% In acetonitrile; a. 54.4 g of 2-chloro-6-trifluoromethyl pyridine are dissolved into a mixture of 350 ml of acetonitrile and 77.4 g of anhydrous piperazine. The mixture is filtered and washed with acetonitrile. The solvent is evaporated. The residue is taken up with dichloromethane and washed with water. The solution is dried over magnesium sulfate. The solvent is evaporated and the residue distilled, to obtain 56.4 g of 1-[6-(trifluoromethyl)-2-pyridinyl]piperazine (81.4% yield), having a boiling point of 103 C. at 0.05 mm Hg.
81.4% In acetonitrile; a. 54.4 g of 2-chloro-6-trifluoromethyl pyridine are dissolved into a mixture of 350 ml of acetonitrile and 77.4 g of anhydrous piperazine. The mixture is filtered and washed with acetonitrile. The solvent is evaporated. The residue is taken up with dichloromethane and washed with water. The solution is dried over magnesium sulfate. The solvent is evaporated and the residue distilled, to obtain 56.4 g of 1-[6-(trifluoromethyl)-2-pyridinyl]piperazine (81.4% yield), having a boiling point of 103 C at 0.05 mm Hg.
With triethylamine; In DMF (N,N-dimethyl-formamide); at 100.0℃; A solution of 2-chloro-6-(trifluoromethyl)pyridine (1.0 g, 5.5 mmol), piperazine (1.4 g, 16.0 mmol), and triethylamine (1.5 mL, 11.0 mmol) were mixed in DMF (10 mL) in a dealed tube. The mixture was heated at 100 C. overnight. The reaction mixture was concentrated and chromatographed on silica gel (ethyl acetate to EA/MeOH/Et3N=9:1:0.5) to give 1.05 g of the desired product. MS calculated for C10H12F3N3: (M+H) 232.1; found 232.1.
  • 3
  • [ 574-98-1 ]
  • [ 127561-18-6 ]
  • [ 139722-72-8 ]
YieldReaction ConditionsOperation in experiment
33% With sodium carbonate; In dichloromethane; b. A mixture of 69.3 g of <strong>[127561-18-6]1-[6-(trifluoromethyl)-2-pyridinyl]piperazine</strong>, and 129.6 g of N-(2-bromoethyl)phthalimide and 57.2 g of sodium carbonate is heated at reflux for 23 hours. The resulting precipitate is filtered off and the ethanol evaporated. The concentrate is dissolved in dichloromethane, washed with water, dried over magnesium sulfate, and evaporated. The resulting precipitate is recrystallized from isopropanol to give 39.5 g of 2-[2-[4-[6-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]ethyl]-1H-isoindole-1,3-dione (yield 33%).
  • 4
  • [ 86604-86-6 ]
  • [ 127561-18-6 ]
  • 6-trifluoromethyl-2-[4-(6-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1<i>H</i>-benzoimidazole [ No CAS ]
  • 7
  • [ 127561-18-6 ]
  • 2-amino-1-[4-(6-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-ethanone [ No CAS ]
  • 8
  • [ 127561-18-6 ]
  • 3-(2,4-dioxo-3,4,7,8-tetrahydro-2<i>H</i>,5<i>H</i>-thiopyrano[4,3-<i>d</i>]pyrimidin-1-yl)-<i>N</i>-{2-oxo-2-[4-(6-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-ethyl}-propionamide [ No CAS ]
  • 9
  • [ 127561-18-6 ]
  • 1-{2-oxo-2-[4-(6-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-ethyl}-3,5,7-triaza-1-azonia-tricyclo[3.3.1.13,7]decane; chloride [ No CAS ]
  • 10
  • [ 109-70-6 ]
  • [ 127561-18-6 ]
  • C13H17ClF3N3 [ No CAS ]
  • 11
  • [ 54512-75-3 ]
  • [ 127561-18-6 ]
  • C15H21ClF3N3 [ No CAS ]
  • 12
  • C9H13ClN2OS [ No CAS ]
  • [ 127561-18-6 ]
  • C19H24F3N5OS*Cl(1-) [ No CAS ]
  • 13
  • C7H9ClN2OS [ No CAS ]
  • [ 127561-18-6 ]
  • C17H20F3N5OS [ No CAS ]
  • 14
  • [ 127561-18-6 ]
  • 1-bromo-4-chloro-2-butene [ No CAS ]
  • C14H17ClF3N3 [ No CAS ]
  • 15
  • C7H9ClN2OS [ No CAS ]
  • [ 127561-18-6 ]
  • C17H21F3N5OS [ No CAS ]
  • 16
  • C8H9ClN2OS [ No CAS ]
  • [ 127561-18-6 ]
  • C18H20F3N5OS [ No CAS ]
  • 17
  • [ 201609-25-8 ]
  • [ 127561-18-6 ]
  • 2a-[4-{4-(6-(trifluoromethyl)pyrid-2-yl)piperazinyl}butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% This compound was synthesized in the same manner as described in Example 87, except that 1-(6-(trifluoromethyl)pyrid-2-yl)piperazine was used in stead of 1-(2-pyridyl)piperazine (yield, 80%). 1H-NMR (CDCl3) delta 1.04-1.17 (1 H, m), 1.29-1.52 (4 H, m), 1.71-1.92 (3 H, m), 2.06-2.20 (2 H, m), 2.22-2.36 (2 H, m), 2.41-2.50 (4 H, m), 2.60-2.70 (1 H, m), 2.80-2.90 (1 H, m), 3.52-3.60 (4 H, m), 6.67 (1 H, d, J=7.6 Hz), 6.74 (1 H, d, J=8.8 Hz), 6.81 (1 H, d, J=7.6 Hz), 6.92 (1 H, d, J=7.6 Hz), 7.12 (1 H, dd), 7.40 (1 H, br s), 7.55 (1 H, dd); MW 458.53 (C25H29F3N4O); Mass spectrum TSP m/z 459 (M+H)+ The thus obtained free compound was dissolved in hydrochloric acid-saturated methanol to obtain its hydrochloric acid salt. MW 494.99 (C25H30ClF3N4O); Mass spectrum TSP m/z 459 (M-HCl)+
  • 18
  • [ 10397-13-4 ]
  • [ 127561-18-6 ]
  • [ 833472-81-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethanol; at 78.0℃; for 8.0h; A mixture of 4, 6-DICHLORO-2-MORPHOLINOPYRIMIDINE (468 mg, 2. 0 mmol), 4- (6- TRIFLUOROMETHYL-2-PYRIDYL) piperazine (462 mg, 2. 0 mmol), potassium carbonate (345 mg, 2. 5 mmol) and ETOH (10 mL) is heated at 78C for 8 hours. The mixture is cooled, diluted with water (20 mL) and extracted with EtOAc (3 x 25 mL). The combined organics are washed with brine (25 mL), dried (MGS04) and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (80% hexane/20% ether) to give the title compound.
  • 19
  • [ 833472-83-6 ]
  • [ 127561-18-6 ]
  • [ 1019850-08-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethanol; at 78.0℃; for 8.0h; A mixture of 4, 6-dichloro-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine (2. 0 mmol), 4- (6- TRIFLUOROMETHYL-2-PYRIDYL) piperazine (462 mg, 2. 0 mmol), potassium carbonate (345 mg, 2. 5 mmol) and ETOH (10 mL) is heated at 78C for 8 hours. The mixture is cooled, diluted with water (20 mL) and extracted with EtOAc (3 x 25 mL). The combined organics are washed with brine (25 mL), dried (MgS04) and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (80% hexane/20% ether) to give the title compound.
  • 20
  • 4-[6-chloro-2-(3-chlorophenyl)pyrimidin-4-yl]morpholine [ No CAS ]
  • [ 127561-18-6 ]
  • 4-(2-(3-chlorophenyl)-6-{4-[3-(trifluoromethyl)(2-pyridyl)]piperazinyl}pyrimidin-4-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90.0℃; for 8.0h; Add 4- (6-TRIFLUOROMETHYL-2-PYRIDYL) piperazine (46 mg, 0. 2 mmol) to a solution of 4- [6-CHLORO-2- (3-CHLOROPHENYL) PYRIMIDIN-4-YL] morpholine (62 mg, 0. 2 mmol), PD2 (dba) 3 (18 mg, 0. 02 MMOL), and BINAP (17 mg, 0. 02 mmol) in toluene (2 mL) under nitrogen, followed by t-BuOK (45 mg, 0. 4 mmol). Stir the mixture at 90C for 8 hours, dilute with aqueous ammonium chloride, and extract with EtOAc (3 x 10 mL). Dry (MGS04) the combined extracts and concentrate under reduced pressure. Purify the residue using flash chromatography on silica gel (50% hexane/50% ether) to give the title compound. MS 505 (M+ 1).
  • 21
  • [ 60703-50-6 ]
  • [ 127561-18-6 ]
  • [ 1020671-23-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethanol; at 78.0℃; for 8.0h; A mixture of 4- (4, 6-DICHLORO-5-METHYLPYRIMIDINYL-2-YL) morpholine (496 mg, 2. 0 MMOL), 4- (6-TIIFLUOROMETHYL-2-PYRIDYL) piperazine (462 mg, 2. 0 mmol), potassium carbonate (345 mg, 2. 5 mmol) and ETOH (10 ML) is heated at 78C for 8 hours. The mixture is cooled, diluted with water (20 mL) and extracted with EtOAc (3 x 25 mL). The combined organics are washed with brine (25 mL), dried (MGS04) and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (80% hexane/20% ether) to give the title compound.
  • 22
  • [ 878809-79-1 ]
  • [ 127561-18-6 ]
  • 4-{6-(3-chloro-4-fluoro-phenyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridin-2-yl}-morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; toluene; at 80.0℃; To a de-gassed mixture of 4-{4-BROMO-6-(3-CHLORO-4-FLUORO-PHENYL)-PYRIDIN-2YL}- morpholine (50 mg, 0. 135 MMOL)), 4-(6-TRIFLUOROMETHYL-2-PYRIDYL) piperazine (37 mg, 0. 162 MMOL), and IM (THF) t-BuOK (0. 162 mmol), in toluene (3mL) under nitrogen add PD2 (dba) 3 (0. 0054 mmol) and BINAP (0. 0067 mmol). Stir the mixture at 80C for overnight, concentrate, extract with EtOAc. Dry over NA2SO4, concentrate under vacuum, and purify by preparative TLC (3 : 1 hexanes/EtOAc) to give 4- {6- (3-CHLORO-4-FLUORO-PHENYL)-4- [4- (3- TRIFLUOROMETHYL-PYRIDIN-2-YL)-PIPERAZIN-I-YL]-PYRIDIN-2-YL}-MORPHOLINE.
  • 23
  • [ 878809-83-7 ]
  • [ 127561-18-6 ]
  • 4-{4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridin-2-yl}-morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; toluene; at 80.0℃; To a de-gassed mixture of 4- [6-CHLORO-4- (3-CHLORO-4-FLUORO-PHENYL)-PYRIDIN-2-YLL- morpholine (50 mg, 0. 153 mmol)), 4-(6-trifluoromethyl-2-pyridyl)piperazine (43 mg, 0. 183 mmol), and IM (THF) t-BuOK (0. 183 mmol), in toluene (3mL) under nitrogen, add PD2 (dba) 3 (0. 006 mmol) and BINAP (0. 008 mmol). Stir the mixture at 80C overnight, concentrate, extract with EtOAc. Dry over NA2S04, concentrate under vacuum, and purify by preparative TLC (3 : 1 hexanes/EtOAc) to give 4-{4-(3-chloro-4-fluoro-phenyl)-6-[4-(3- TRIFLUOROMETHYL-PYRIDIN-2-YL)-PIPERAZIN-1-YL]-PYRIDIN-2-YL}-MORPHOLINE.
  • 24
  • [ 624734-30-1 ]
  • [ 127561-18-6 ]
  • [ 872592-68-2 ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; To a solution of <strong>[127561-18-6]1-[6-(trifluoromethyl)pyridin-2-yl]piperazine</strong> (249 mg, 1.08 mmol), (1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid (300 mg, 1.10 mmol), triethylamine (0.45 mL, 3.2 mmol) in methylene chloride (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (524 mg, 1.18 mmol). After being stirred overnight, the reaction was quenched with saturated sodium NaHCO3. The resulting solution was extracted with EtOAc three times. The combined organic layers were dried (MgSO4) and concentrated. Purification by column chromatography on silica gel (20% EA/hex to 40% EA/hexanes) provided 310 mg of the desired product. MS calculated for C24H36F3N4O3: (M+H) 485.3; found 485.3.
  • 25
  • [ 134578-93-1 ]
  • [ 127561-18-6 ]
  • [ 142494-17-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In dichloromethane; butan-1-ol; EXAMPLE III Method of Making 1-[4-[4-[6-(Trifluoromethvl)-2-Pyridinyl]-1-Piperazinyl]Butyl]-2-Pyrrolidinone (E)-2-butenedioate (1:1) salt 9 g of 1-(4-bromobutyl)-2-pyrrolidinone and 7.6 g of <strong>[127561-18-6]1-[6-(trifluoromethyl)-2-pyridinyl]-piperazine</strong> were mixed with 100 ml of butanol. 4.3 g of sodium carbonate were added, and the mixture is refluxed for 3 hours. The precipitate is filtered and washed with butanol, and the filtrate is then evaporated. The residue was dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, after which the solvent was evaporated to obtain 12.5 g of 1-[4-[4-[6-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]-butyl]-2-pyrrolidinone.
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; at 20.0℃; for 3.0h; General procedure: 1- (5- (trifluoromethyl) pyridin-2-yl) piperazine (13.3 g, 40.0 mmol) was added to 150 mL of a 4N hydrochloric acid-dioxane solution, and the reaction was stirred at room temperature for 3 hours, and the solvent was distilled off under reduced pressure. The residue was adjusted to pH 8-9 with 15% Na2CO3 solution, extracted twice with ethyl acetate, and the organic layers were combined, washed with water and saturated NaCl aqueous solution, and dried with anhydrous Na2SO4 to obtain 8.42 g of A-8, yield 91. %,
  • 27
  • C21H29NO4 [ No CAS ]
  • [ 127561-18-6 ]
  • C31H39F3N4O3 [ No CAS ]
  • 28
  • [ 127561-18-6 ]
  • [ 872673-23-9 ]
  • 29
  • [ 127561-18-6 ]
  • C25H37F3N4O3 [ No CAS ]
  • [ 1310796-75-8 ]
  • 30
  • 1,1’-thiocarbonyldiimidazole [ No CAS ]
  • [ 76-05-1 ]
  • [ 127561-18-6 ]
  • [ 1542214-14-1 ]
  • 31
  • [ 54512-75-3 ]
  • [ 127561-18-6 ]
  • C19H24F3N5OS*Cl(1-) [ No CAS ]
  • 32
  • [ 127561-18-6 ]
  • C18H20F3N5OS [ No CAS ]
  • 33
  • [ 127561-18-6 ]
  • C17H20F3N5OS [ No CAS ]
  • 34
  • [ 127561-18-6 ]
  • C17H21F3N5OS [ No CAS ]
  • 35
  • [ 368-43-4 ]
  • [ 127561-18-6 ]
  • 1-(phenylsulfonyl)-4-(6-(trifluoromethyl)pyridin-2-yl)piperazine [ No CAS ]
 

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