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Chemical Structure| 131922-05-9
Chemical Structure| 131922-05-9
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Product Details of [ 131922-05-9 ]

CAS No. :131922-05-9 MDL No. :MFCD07373382
Formula : C5H9F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :YNEJOOCZWXGXDU-UHFFFAOYSA-N
M.W : 154.13 Pubchem ID :18519725
Synonyms :

Safety of [ 131922-05-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P273-P280-P305+P351+P338-P310 UN#:3263
Hazard Statements:H314-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 131922-05-9 ]

* 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 [ 131922-05-9 ]

[ 131922-05-9 ] Synthesis Path-Downstream   1~18

  • 1
  • 1-benzyl-3-(trifluoromethyl)piperazine [ No CAS ]
  • [ 131922-05-9 ]
YieldReaction ConditionsOperation in experiment
32% With hydrogen;5%-palladium/activated carbon; In water; acetic acid; at 70℃; under 2250.23 Torr; INTERMEDIATE 45 2- (Trifluoromethyl) piperazine* 1-Benzyl-3- (trifluoromethyl) piperazine (0.74 g, 3.0 mmol; Intermediate 44) was dissolved in acetic acid (70 mL) and water (5 mL). Pd, 5 % on carbon, (0.074 g) was added and hydrogenatation was performed at 3 bar and 70 C overnight. The reaction mixture was filtered through Celite and the pad was rinsed with water (5 mL). Solvents were removed in vacuo, toluene (20 mL) added to the residue, followed by re-concentration in vacuo to remove residual water. The desired product sublimated on the evaporator and 0.15 g (32 %) was collected as a white powder. lH NMR (270 MHz, methanol-d4) 8 ppm 2.67-2. 87 (m, 3 H) 2.91-3. 05 (m, 2 H) 3.12-3. 21 (m, 1 H). MS (ESI+) m/z 155. *Previously described in Rec. Trav. Chim. Pays-Bas 1995,114, 97-102.
With hydrogen; acetic acid;5%-palladium/activated carbon; In methanol; for 12h; l-Benzyl-3-(trifluoromethyl)piperazine 34a (4.1 mmol) is dissolved in MeOH (50 mL) followed by addition of AcOH (2.0 mL) and 5% mol of Pd/C. The flask is charged with a hydrogen balloon and stirred for 12 h. The mixture is filtered over celite and the filtrate is <n="61"/>concentrated to afford 2-(trifluoromethyl)piperazine 35a, which is used without further purification. MS (m/z) (M+l)+: 155.1.
  • 2
  • [ 478617-58-2 ]
  • [ 131922-05-9 ]
  • [ 856678-35-8 ]
YieldReaction ConditionsOperation in experiment
44% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In xylene; at 100℃; for 72h; INTERMEDIATE 46 1- (5-Nitro-l-benzofuran-7-yl)-3- (trifluoromethyl) piperazine To 7-iodo-5-nitro-1-benzofuran (231.4 mg, 0.08 mmol) the following was added: Xantphos (92.6 mg, 0.16 mmol), Pd2dba3 (36. 6 mg, 0.04 mmol), sodium tert-butoxide (215.4 mg, 2.24 mmol), 2- (trifluoromethyl) piperazine (148.1 mg, 0.96 mmol ; Intermediate 45) and xylene (23 mL). The resulting mixture was stirred at 100 C for 3 days. Filtration through Celite and purification by flash chromatography, using EtOAc: heptane (1: 1) as eluent, furnished 1- (5-nitro-1-benzofuran-7-yl)-3- (trifluoromethyl) piperazine (112 mg, 44 % yield). HPLC 90 %, RT=1. 648 min (System A; 10-97 % MeCN over 3 min), MS (ESI+) m/z 316 (M+H) +.
YieldReaction ConditionsOperation in experiment
Step 4 The crude product from the step 3 was dissolved in HOAc (20 ml) with 10 mg 10% palladium on active carbon. The reaction mixture was hydrogenated under pressure (40-50 psi) for 8 hours. The solid was filtered and removed. The filtrate was concentrated to afford 2-trifluoromethylpiperazine XXVII as a HOAc salt, which was pure enough for the further reactions. 2-Trifluoromethylpiperazine XXVII as its HOAc (2 equivalents) salt: 1H NMR (300 MHz, CD3OD) δ 3.80-2.80 (m, 7H), 1.95 (s, 6H); 13C NMR (75 MHz, CD3OD) δ 174.5, 53.8, 53.3, 42.7, 41.3, 40.8, 19.8; HRMS m/z: (M+H)+calcd for C5H10F3N2: 155.0796, found 155.0801.
  • 4
  • [ 1353628-61-1 ]
  • [ 131922-05-9 ]
  • [ 76-05-1 ]
  • (x)C2HF3O2*C24H26Cl2F3N7O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Intermediate 131<strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (18.5 mg, 0.12 mmol) and sodium bicarbonate (20.0 mg, 0.24 mmol) were added to a solution of intermediate 56 (60 mg, 0.12 mmol) in acetonitrile (0.60 mL) and water (0.60 mL) and the reaction mixture was stirred at room temperature. After 20 h, the reaction mixture was purified by preparatory HPLC (5-100% MeCN/H20, 0.1% trifluoroacetic acid modifier) to afford intermediate 131 (31.1 mg, 35%) as a white solid trifluoroacetate salt.LCMS (ESI) m/z 620.09 [M + H]+, tR = 2.83 min.
  • 5
  • [ 22118-09-8 ]
  • [ 1404048-56-1 ]
  • [ 131922-05-9 ]
  • [ 1403897-05-1 ]
YieldReaction ConditionsOperation in experiment
Example 113: 1 -{6-Benzyl-3,3-dimethyl-1 H,2H,3H-pyrrolo[3,2-c]pyridin(trifluoromethyl)piperazin-l -yl]ethan-1 -oneA solution of bromoacetyl chloride (0.535 g, 3.4 mmol) in DCM (5 mL) was added to a two phase mixture of 6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine (0.467 g, 1 .7 mmol) sodium hydrogen carbonate (1 .43 g, 17 mmol), DCM (20 mL) and water (25 mL) with ice cooling over 0.1 h. The mixture was stirred at -0 C for 2 h then the organic phase was separated and the aqueous phase was extracted with DCM (25 mL). The combined organic phases were dried (Na2S04) and evaporated in vacuo to give an oil which was purified by chromatography (Si02, 20 - 50% EtOAc in petrol) gave an oil which solidified. A mixture of this material (0.081 g, 0.23 mmol) 2-trifluoromethylpiperazine (0.039 g, 0.25 mmol), potassium carbonate (0.064 g, 0.46 mmol) and acetonitrile (2 mL) was stirred at 20 C for 4 h. The mixture was partitioned between water (30 mL) and DCM (3 x 20 mL) and the combined extracts were dried (Na2S04) and evaporated in vacuo to give an oil.Chromatography (Si02, 0 - 20% MeOH in EtOAc),gave impure product and this was followed by further chromatography (Si02, 0 - 5% MeOH in EtOAc) then preparative HPLC (basic method) to give the title compound (0.005 g). 1H NMR (Me-d3-OD): 8.24 (1 H, s), 7.94 (1 H, s), 7.34-7.23 (4H, m), 7.23-7.16 (1 H, m), 4.1 1 (2H, s), 4.03-3.92 (2H, m), 3.45 (3H, s), 3.08 (1 H, d), 3.04-2.81 (3H, m), 2.32 (2H, q), 1.42 (6H, s). MS: [M+H]+ = 433.
  • 6
  • [ 1404048-56-1 ]
  • [ 131922-05-9 ]
  • [ 1403897-08-4 ]
  • 7
  • [ 42098-25-9 ]
  • [ 131922-05-9 ]
  • [ 1428576-51-5 ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine; In ethanol; at 140℃; for 5h; Step A. (+-)-1-(1-Methyl-4-nitro-1H-pyrazol-5-yl)-3-(trifluoromethyl)piperazine A mixture of (+-)-<strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (1 g, 6.2 mmol), 5-chloro-1-methyl-4-nitro-1H-pyrazole (2.1 g, 13 mmol), DIPEA (2.4 g, 18.6 mmol) in EtOH (10 mL) was heated in a microwave oven at 140 C. for 5 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by silica gel chromatography using DCM/MeOH (10:1) as eluting solvents to afford (+-)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)-3-(trifluoromethyl)piperazine as a yellow oil (1.8 g, 99%). MS (ESI) m/z: 280 [M+H+].
  • 8
  • [ 5292-43-3 ]
  • C16H11Cl2N3O2 [ No CAS ]
  • [ 131922-05-9 ]
  • C27H29ClF3N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 1 : Intermediate 3001 D (200 mg, 0.574 mmol) is charged in a vial and dissolved in DMF (5 mL). Potassium carbonate (158 mg, 1 .15 mmol, 2.00 eq) and tert-butyl bromoacetate (TCI) (168 mg, 0.862 mmol, 1 .50 eq) are added and solution is stirred at RT for 72 h. Diisopropylethylamine (200 μΙ_, 1 .15 mmol, 2.00 eq) is added followed by 2- (trifluoromethyl)piperazine (Matrix) (133 mg, 0.862 mmol, 1 .50 eq) and the solution is stirred at 75 C for 24 h. The cooled solution is then diluted with EtOAc and washed with water. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure to provide intermediate 3009A.
  • 9
  • [ 1133116-39-8 ]
  • [ 131922-05-9 ]
  • [ 1509949-12-5 ]
  • 10
  • [ 24424-99-5 ]
  • [ 131922-05-9 ]
  • [ 886779-69-7 ]
YieldReaction ConditionsOperation in experiment
90% In dichloromethane; at 20℃; for 3h; To a solution of <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (135 mg, 0.876 mmol) in DCM (6 ml) were added di-tert-butyl dicarbonate (0.224 ml, 0.963 mmol) and the resulting mixture was stirred at RT for 3 h, then concentrated and the residue was purified via silica gel chromatography (0 - 100 % EtOAc in hexanes) to give tert-butyl 3 -(trifluoromethyl)piperazine-l -carboxylate (200 mg, 0.787 mmol, 90 % yield) as a pale yellow solid. MS (ES+) C10H17F3N2O2 requires: 254, found: 155 [M+H]+- Boc group.
3.2 g In tetrahydrofuran; at 20℃; for 14h; Into a 250-mL round-bottom flask, was placed <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (4.00 g, crude), THF (100.00 mL), Boc2O (8.50 g, 38.947 mmol, 1.50 equiv). The resulting solution was stirred for 14 hr at room temperature. The resulting mixture was concentrated. The residue was applied onto a silica gel column and purified with ethyl acetate/petroleum ether (1:1). This resulted in 3.2 g (48.50%) of tert-butyl 3-(trifluoromethyl)piperazine-1-carboxylate as a white solid. H-NMR: (300 MHz, Chloroform-d) δ 4.13 (d, J = 16.2 Hz, 1H), 3.94 - 3.74 (m, 1H), 3.24 (dtd, J = 10.2, 6.6, 3.0 Hz, 1H), 3.16 - 2.87 (m, 3H), 2.78 (td, J = 12.7, 11.7, 4.8 Hz, 1H), 2.07 (s, 1H), 1.49 (s, 9H).
3.2 g In tetrahydrofuran; at 20℃; for 14h; Into a 250-mL round-bottom flask, was placed <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (4.00 g, crude), THF (100.00 mL), Boc2O (8.50 g, 38.947 mmol, 1.50 equiv). The resulting solution was stirred for 14 hr at room temperature. The resulting mixture was concentrated. The residue was applied onto a silica gel column and purified with ethyl acetate/petroleum ether (1:1). This resulted in 3.2 g (48.50%) of tert-butyl 3-(trifluoromethyl)piperazine-1-carboxylate as a white solid. H-NMR: (300 MHz, Chloroform-d) δ 4.13 (d, J = 16.2 Hz, 1H), 3.94 - 3.74 (m, 1H), 3.24 (dtd, J = 10.2, 6.6, 3.0 Hz, 1H), 3.16 - 2.87 (m, 3H), 2.78 (td, J = 12.7, 11.7, 4.8 Hz, 1H), 2.07 (s, 1H), 1.49 (s, 9H).
  • 11
  • [ 131922-05-9 ]
  • tert-butyl 4-(5-bromopyridin-2-yl)-3-(trifluoromethyl)piperazin-1-carboxylate [ No CAS ]
  • 12
  • [ 131922-05-9 ]
  • tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-3-(trifluoromethyl)piperazin-1-carboxylate [ No CAS ]
  • 13
  • [ 131922-05-9 ]
  • tert-butyl 4-(5-(3-fluoro-4-(5-oxo-1-propyl-1H-1,2,4-triazol-4(5H)-yl)phenyl)pyridin-2-yl)-3-(trifluoromethyl)piperazin-1-carboxylate [ No CAS ]
  • 14
  • [ 350-46-9 ]
  • [ 131922-05-9 ]
  • 1-(4-nitrophenyl)-3-(trifluoromethyl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;Inert atmosphere; A suspension of 1-fluoro-4-nitrobenzene (0.915 g, 6.49 mmol), <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (1.00 g, 6.49 mmol) and potassium carbonate (1.345 g, 9.73 mmol) in anhydrous DMF (5 mL) was heated to 50 C under a nitrogenatmosphere overnight. The reaction mixture was allowed to cool to room temperature, diluted with water (30 mL) and stirred at room temperature for 15 minutes. The precipitated solid was isolated by filtration, washed with water and sucked dry to give the title compound as ayellow solid (1.47 g, 82%) . ‘H NMR (300 MHz, CDC13) : 38.15 (dt, 2H), 6.87 (dt, 2H), 3.91 (br d, 1H), 3.74 (ddd,1H), 3.39-3.54 (m, 1H), 3.25 (dd, 1H), 2.93-3.16 (m, 3H),2.00 (br s, 1H) . LCMS (Method C) : = 1.12 mi m/z = 276[M+H] .
73.8% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;Inert atmosphere; In a 50 mL round bottom flask was added 4A (290 mg, 1.88 mmol) dissolved in DMF (2 mL), potassium carbonate (390 mg, 2.82 mmol), 4B (265 mg, 1.88 mmol) was added and stirred in a 50C oil bath under nitrogen atmosphere. After overnight reaction, the reaction solution was added with water, petroleum ether, stirred for 30 min, suction filtered, washed successively with water and petroleum ether, and the resulting cake was purified by silica gel column chromatography (dichloromethane:methanol 100:1) to give a yellow solid 4C (382 mg). Yield 73.8%).
  • 15
  • [ 131922-05-9 ]
  • tert-butyl 4-(4-nitrophenyl)-2-(trifluoromethyl)piperazine-1-carboxylate [ No CAS ]
  • 16
  • [ 131922-05-9 ]
  • tert-butyl 4-(4-aminophenyl)-2-(trifluoromethyl)piperazine-1-carboxylate [ No CAS ]
  • 17
  • 6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinoline-2-carboxylic acid [ No CAS ]
  • [ 125700-67-6 ]
  • [ 131922-05-9 ]
  • [3-(trifluoromethyl)piperazin-1-yl](6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinolin-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine; In dimethyl sulfoxide; acetonitrile; Example 20 [3-(trifluoromethyl)piperazin-1-yl](6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinolin-2-yl)methanone To a mixture of the product from Example 1D (107.9 mg, 0.323 mmol) and O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU, 156.4 mg, 0.487 mmol) in dimethyl sulfoxide (1 mL) at room temperature was added triethylamine (0.1 mL, 0.72 mmol) followed by <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (79.5 mg, 0.518 mmol). After 3 h, the mixture was diluted with methanol (1 mL) and purified by reverse phase preparative HPLC on a Waters Nova-Pak HR C18.6 μm 60 Å Prep-Pak cartridge column (40 mm*100 mm) using a gradient of 10% to 100% acetonitrile in 10 mM aqueous ammonium acetate over 12 minutes at a flow rate of 70 mL/minute to yield 104.3 mg (69%) of the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1:1 mixture of rotamers 8.57-5-61 (m, 1H), 8.50 (dd, J=8.5, 4.6 Hz, 1H), 8.31 (dd, J=8.5, 2.4 Hz, 1H), 8.10 (t, J=9.0 Hz, 1H), 7.90 (t, J=2.7 Hz, 1H), 7.70-7.78 (m, 2H), 7.40 (dd, J=8.5, 3.7 Hz, 1H), 4.36 (dd, J=12.5, 3.1 Hz, 0.5H), 4.11-4.14 (m, 0.5H), 4.02 (dd, J=13.3, 2.3 Hz, 0.5H), 3.03-3.64 (m, 4H), 2.67-2.90 (m, 1.5H); MS (ESI) m/z 471.1 [M+H]+.
  • 18
  • 6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinoline-2-carboxylic acid [ No CAS ]
  • [ 131922-05-9 ]
  • [3-(trifluoromethyl)piperazin-1-yl](6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinolin-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate; triethylamine; In dimethyl sulfoxide; at 20℃; for 3h; General procedure: To a mixture of 6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinoline-2-carboxylic acid, 58 (108 mg, 0.323 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′ -tetramethyluronium tetrafluoroborate (HATU) (156 mg,0.487 mmol) in DMSO (1 mL) at ambient temperature was added triethylamine(0.1 mL, 0.720 mmol) followed by <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong>(79.5 mg, 0.518 mmol) and stirred for 3 h. The mixture wasdiluted with methanol (1 mL) and purified by reverse phase preparativeHPLC on a Waters Nova-Pak HR C18 60 Å Prep-Pak cartridge column(40 mm × 100 mm) using a gradient of 10% to 100% acetonitrile in 10mM aqueous ammonium acetate over 12 min at a flow rate of 70 mL/minute to yield [3-(trifluoromethyl)piperazin-1-yl](6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinolin-2-yl)methanone 59, a 1:1mixture of rotamers (104 mg 69% yield). 1H NMR (400 MHz, DMSO-d6)δ ppm 1:1 mixture of rotamers 8.57-5-61 (m, 1H), 8.50 (dd, J = 8.5, 4.6Hz, 1H), 8.31 (dd, J = 8.5, 2.4 Hz, 1H), 8.10 (t, J = 9.0 Hz, 1H), 7.90 (t, J= 2.7 Hz, 1H), 7.70-7.78 (m, 2H), 7.40 (dd, J = 8.5, 3.7 Hz, 1H), 4.36(dd, J = 12.5, 3.1 Hz, 0.5H), 4.11-4.14 (m, 0.5H), 4.02 (dd, J = 13.3,2.3 Hz, 0.5H), 3.03-3.64 (m, 4H), 2.67-2.90 (m, 1.5H); MS (ESI) m/z471.1 [M + H]+. 13C NMR (101 MHz, DMSO) δ 166.8, 166.5, 165.3,153.2, 152.9, 151.7, 151.5, 145.3 (q, J = 4.3 Hz), 143.8, 143.4, 137.8 (q,J = 3.1 Hz), 137.1, 130.8, 130.7, 128.4, 128.4, 126.1, 126.0, 125.4 (qd,J = 281.5, 12.6 Hz), 123.8 (q, J = 271.5 Hz), 121.2, 120.8 (q, J = 32.7Hz), 120.7, 118.0, 112.2 (d, J = 2.3 Hz), 54.9 (q, J = 27.9 Hz), 54.4 (q, J= 27.7 Hz), 46.9, 45.5, 43.5, 42.9, 42.2, 40.1.
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