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[ CAS No. 383907-17-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 383907-17-3
Chemical Structure| 383907-17-3
Chemical Structure| 383907-17-3
Structure of 383907-17-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 383907-17-3 ]

CAS No. :383907-17-3 MDL No. :MFCD01311991
Formula : C7H7F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :FUJKUIAVFVGTGS-UHFFFAOYSA-N
M.W : 176.14 Pubchem ID :3521850
Synonyms :

Calculated chemistry of [ 383907-17-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.61
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 1.49
Log Po/w (WLOGP) : 3.15
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.18 mg/ml ; 0.00669 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 2.14 mg/ml ; 0.0122 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.204 mg/ml ; 0.00116 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 383907-17-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 383907-17-3 ]

* 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 [ 383907-17-3 ]

[ 383907-17-3 ] Synthesis Path-Downstream   1~41

  • 1
  • [ 624-28-2 ]
  • [ 383907-17-3 ]
  • [ 956136-81-5 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In 1,4-dioxane at 100℃; for 18h; Sealed vessel; 4-12.A 2,5-dibromopyridine (474 mg, 2 mmol) and 2-Methyl-6-trifluoromethyl-pyridin-3-ylamine (352 g, 2 mmol) were dissolved in 1 ,4-dioxane (4 mL) in a pressure vessel. Pd2dba3 (55 mg, 0.06 mmol) and XANTPHOS (46 mg, 0.08 mmol) were added, followed by cesium carbonate (1.3 g, 4 mmol). The mixture was sparged with nitrogen for 10 minutes, then the vessel was sealed and heated at 100 0C for 18 hours. The mixture was partitioned between EtOAc and saturated aqueous NH4CI, then the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated via rotary evaporation. The crude material was purified via column chromatography on silica gel, eluting with a gradient of EtOAc/hexanes (7-60%) to obtain the target compound as a solid: 1H NMR (400 MHz, CDCI3) δ ppm 2.62 (s, 3 H) 6.36 (br. s., 1 H) 6.75 (d. J=8.59 Hz, 1 H) 7.53 (d, J=8.34 Hz, 1 H) 7.69 (dd, J=8.84, 2.53 Hz, 1 H) 8.32 - 8.37 (m, 2 H); MS (M+H)+ 334.7.
  • 4
  • [ 383907-17-3 ]
  • [ 944317-26-4 ]
YieldReaction ConditionsOperation in experiment
With iodine; isopentyl nitrite In chloroform at 20 - 80℃; for 4.5h; 10.A A mixture of 3-amino-2-methyl-6-(trifluoromethyl)pyridine (500 mg, 2.84 mmol), isoamyl nitrite 760 μL, 5.68 mmol) and iodide (793 mg, 3.12 mmol) in dry CHCl3 (10 mL) was stirred at room temperature for 0.5 h. The mixture was heated at 80 0C under N2 for 4 h. The reaction mixture was quenched with saturated Na2S2O3 then partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 3-iodo-2-methyl~6-(trifluoromethyl)pyridine. LCMS calc. = 288.0; found = 288.0 (M+l)+. 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J = 8.0 Hz3 1 H); 7.22 (d, J= 8.1 Hz, 1 H); 2.83 (s, 3 H).
  • 5
  • [ 383907-17-3 ]
  • [ 463-71-8 ]
  • [ 1140496-11-2 ]
  • [ 1140495-47-1 ]
YieldReaction ConditionsOperation in experiment
26.9% Stage #1: 2-methyl-6-(trifluoromethyl)pyridin-3-amine; thiophosgene With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h; Stage #2: (R)-4-(4-chlorobenzyl)-3-ethyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole hydrochloride In dichloromethane at 0 - 20℃; 56 Example 56 (R)-2-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)-N-(2-methyl-6-(trifluoromethyl)pyridin-3-yl)pyrrolidine-1-carbothioamide. To a stirring solution of thiophosgene (0.23 mL, 3 mmol) in 50 mL of CH2Cl2 at 0° C. was added dropwise a mixed solution of 2-methyl-6-(trifluoromethyl)pyridin-3-amine (0.528 g, 3 mmol) and N,N-diisopropylethylamine (0.522 mL, 3 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at 0° C., warming up to room temperature within an hour. Then the mixture was cooled at 0° C. and to it was added a solution of the (R)-4-(4-chlorobenzyl)-3-ethyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole HCl salt (1.05 g, 3 mmol) and N,N-diisopropylethylamine (1.044 mL, 6 mmol) in dichloromethane (10 mL) slowly. The resulting mixture was stirred 0° C. for 30 minutes, then at room temperature overnight. The reaction mixture was treated with sat. aqueous NaHCO3 (10 mL) and brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography purification (Hex/EtOAc with 10% of MeOH) afforded the desired product as yellow solid (0.4 g, 26.9%). 1H NMR (300 MHz, CDCl3) 1.96-2.19 (m, 3H), 2.30 (s, 3H), 2.56 (s, 3H), 2.69-2.72 (m, 1H), 3.74-3.77 (m, 1H), 4.21-4.25 (m, 1H), 5.02-5.08 (d, 1H), 5.51-5.57 (d, 1H), 5.59-5.60 (d, 1H), 7.00-7.03 (d, 2H), 7.31-7.35 (dd, 2H), 7.44-7.46 (d, 1H), 7.66 (s, 1H), 7.77-7.80 (d, 1H). MS: calculated: 494.96, found (MH+): 495.0.
  • 6
  • [ 117519-09-2 ]
  • [ 13061-96-6 ]
  • [ 383907-17-3 ]
  • 8
  • [ 383907-17-3 ]
  • [ 108-24-7 ]
  • [ 1383735-00-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane for 144h; To a solution of K-1 (5.00 g, 28.4 mmol) in DCM (25 mL) is added acetic anhydride (3.30 mL, 34.2 mmol) followed by DIPEA (5.6 mL, 32.2 mmol) and DMAP (25.0 mg, 0.20 mmol). After 6 days, the reaction is concentrated and diluted with water, made basic with NaHCO3, and extracted with EtOAc (3 x 50 mL). The combined organic layers are washed with brine (2 x 40 mL), dried over magnesium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with DCM -heptane (1: 1) and then ethyl acetate. Mixed fractions are purified by silica gel chromatography eluting with EtO Ac-heptane (1:9, then 2:8, then 100:0) to provide K-2.
  • 9
  • [ 383907-17-3 ]
  • [ 1256836-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: potassium acetate; acetic anhydride / toluene / 16 h / 80 °C 3: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C
  • 10
  • [ 383907-17-3 ]
  • [ 1383735-01-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / microwave irradiation
  • 11
  • [ 383907-17-3 ]
  • [ 1383735-52-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / microwave irradiation 4.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / 1,4-dioxane; methanol / 3 h / 50 °C / 15514.9 - 18100.7 Torr
  • 12
  • [ 383907-17-3 ]
  • [ 1383735-56-5 ]
  • [ 1383735-55-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / microwave irradiation 4.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / 1,4-dioxane; methanol / 3 h / 50 °C / 15514.9 - 18100.7 Torr 5.1: AD column / isopropyl alcohol; n-heptane / Resolution of racemate
  • 13
  • [ 383907-17-3 ]
  • 4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
4 g With N-Bromosuccinimide In acetonitrile at 20℃; for 1.5h; 4.1 Step 1:
Synthesis of 4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine To a solution of 3.0 g of 2-methyl-6-(trifluoromethyl)pyridin-3-amine in 30 ml of acetonitrile, 3.03 g of N-bromosuccinimide was added at room temperature. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 10:0 to 50:50) as the eluent to obtain 4.0 g of the desired product as a brown solid. Melting point: 40-41° C. 1H-NMR (CDCl3): δ7.61 (s, 1H), 4.40 (brs, 2H), 2.52 (s, 3H).
4.0 g With N-Bromosuccinimide In acetonitrile at 20℃; for 1.5h; 4.1 Step 1: Synthesis of 4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine To a solution of 3.0 g of 2-methyl-6-(trifluoromethyl)pyridin-3-amine in 30 ml of acetonitrile was added 3.03 g of N-bromosuccinimide at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to give 4.0 g of the desired product in brown.Obtained as a colored solid.
  • 14
  • [ 383907-17-3 ]
  • 4-bromo-N,2-dimethyl-6-(trifluoromethyl)pyridin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice
  • 15
  • [ 383907-17-3 ]
  • 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube 4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 20 °C 5.1: acetic acid / 3 h / Reflux
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / 20 °C 5.1: acetic acid / 3 h / Reflux
  • 16
  • [ 383907-17-3 ]
  • 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube 4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 20 °C 5.1: acetic acid / 3 h / Reflux 6.1: 3-chloro-benzenecarboperoxoic acid / chloroform; water / 2 h / 20 °C / Cooling with ice
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / 20 °C 5.1: acetic acid / 3 h / Reflux 6.1: 3-chloro-benzenecarboperoxoic acid / chloroform; water / 2 h / 20 °C / Cooling with ice
  • 17
  • [ 383907-17-3 ]
  • 3-(ethylthio)-N-[2-methyl-3-(methylamino)-6-(trifluoromethyl) pyridin-4-yl]-6-(trifluoromethyl)imidazo[ 1,2-a] pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube 4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 20 °C
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / 20 °C
  • 18
  • [ 383907-17-3 ]
  • N<SUP>3</SUP>,2-dimethyl-6-(trifluoromethyl)pyridine-3,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave
  • 19
  • [ 383907-17-3 ]
  • 2-(pyridin-2-yl)-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2.1: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3.1: potassium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C 3.2: 48 h / 80 °C
  • 20
  • [ 383907-17-3 ]
  • 5-(2-methyl-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridin-3-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: sodium / ethyl acetate 4: acetic acid; bromine / 3 h / 70 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 18 h / 90 °C / Sealed tube; Inert atmosphere
  • 21
  • [ 383907-17-3 ]
  • 3-bromo-2-methyl-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: sodium / ethyl acetate 4: acetic acid; bromine / 3 h / 70 °C
  • 22
  • [ 383907-17-3 ]
  • 7-methyl-5-(2-methyl-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridin-3-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: sodium / ethyl acetate 4: acetic acid; bromine / 3 h / 70 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 18 h / 110 °C / Inert atmosphere
  • 23
  • [ 383907-17-3 ]
  • 3-bromo-2-(difluoromethyl)-5-(trifluoromethyl)pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2.1: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3.1: caesium carbonate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 1 h / 95 °C 4.1: bromine; sulfuric acid / 0.5 h / 20 °C 4.2: 0.67 h / 20 °C
  • 24
  • [ 383907-17-3 ]
  • 5-(trifluoromethyl)-3a,7a-dihydro-1H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C
  • 25
  • [ 383907-17-3 ]
  • 2-phenyl-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: sodium fluoride; cesium fluoride; sodium / acetonitrile / 22 h / 20 °C
  • 26
  • [ 383907-17-3 ]
  • 2-(difluoromethyl)-5-(trifluoromethyl)pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: caesium carbonate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 1 h / 95 °C
  • 27
  • [ 383907-17-3 ]
  • 2-isopropyl-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: caesium carbonate / N,N-dimethyl-formamide / 54 h / 20 °C
  • 28
  • [ 383907-17-3 ]
  • 2-methyl-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3: sodium / ethyl acetate
  • 29
  • [ 117519-09-2 ]
  • [ 823-96-1 ]
  • [ 383907-17-3 ]
YieldReaction ConditionsOperation in experiment
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 110℃; for 18h;Inert atmosphere; To a suspension of 3-amino-2-chloro-6-(trifluorom- ethyl)pyridine (9.0 g, 46 mmol) in 1,4-dioxane (144 mE) were added trimethylboroxine (19.0 mE, 136 mmol), Pd(dppf)C1 2 (1.7 g, 2.3 mmol) and K2C03 (19.0 g, 137 mmol). The reaction mixture was stirred at 1100 C. for 18 h under argon. The mixture was diluted with EtOAc (36 mE), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (Si02 1% (2M NH3 in EtOH)/ CHC13). The residue was triturated with a mixture of n-hexane and diisopropyl ether (9:1, 10 mE) to give the title compound (6.5 g, 81% yield) as a tan crystalline solid. MS (ESI): mass calcd. for C7H7F3N2, 176.1; mlz found, 177.0 [M+H].
  • 30
  • [ 383907-17-3 ]
  • [ 108-24-7 ]
  • 1-(5-(trifluoromethyl)-3a,7a-dihydro-1Hpyrazolo[4,3-b]pyridin-1-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With 18-crown-6 ether; potassium acetate; isopentyl nitrite In chloroform at 100℃; for 2h; Step B: 1 -(5-(Trifluoromethyl)-3a,7a-dihydro-1 Hpyrazolo[4,3-b]pyridin-1 -yl)ethan- 1-one. To a solution of 2-methyl-6-(trifluoromethyl)pyridin-3-amine (2.5 g, 14 mmol) in CHC13 (65 mE) were added KOAc (1.7 g, 17.3mmol), 1,4,7,10,13,1 6-hexaoxacyclooctadecane (18-Crown-6, 375 mg, 1.42 mmol), acetic anhydride (5.4 mE, 57 mmol) and isopentyl nitrite (3.8 mE, 28 mmol). The reaction mixture was stirred at 1000 C. for 2 h, cooled to it, filtered, and concentrated in vacuo. The residue was triturated with diisopropyl ether (5 mE) to give the title compound (1.6 g, 49% yield) as a pale orange crystalline solid, which was used directly in the next step without thrther purification.
  • 31
  • [ 383907-17-3 ]
  • N-benzyl-1-(pentan-2-yl)piperidin-4-amine [ No CAS ]
  • [ 530-62-1 ]
  • 1-benzyl-3-(2-methyl-6-(trifluoromethyl)pyridin-3-yl)-1-(1-(pentan-2-yl)piperidin-4-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methyl-6-(trifluoromethyl)pyridin-3-amine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 3h; Stage #2: N-benzyl-1-(pentan-2-yl)piperidin-4-amine In tetrahydrofuran at 20℃; for 16h;
  • 32
  • [ 383907-17-3 ]
  • [ 6160-65-2 ]
  • 3-isothiocyanato-2-methyl-6-(trifluoromethyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 4h; 3-isothiocvanato-2-methyl-6-(trifluoromethyl)pyridine l,l'-Thiocarbonyldiimidazole (516 mg, 2.75 mmol, 95 mass%) and then hydrochloric acid in dioxane (1.25 mL, 5.00 mmol, 4 mol/L) were added to a solution of 2-methyl-6-(trifluoromethyl)pyridin-3- amine (464 mg, 2.50 mmol, 95 mass%) in DCM (7.5 mL) under air. The reaction was stirred at r.t. for 4 hours, concentrated in vacuo and purified by flash column chromatography on silica (gradient elution with 0% to 50% EtOAc in isohexanes) to give the title compound (360 mg, 66 % Yield). A few drops of isobutylamine were added to the LCMS sample of the product before analysis, LCMS [M+H]+ 292, RT 1.39 minutes [M = l-isobutyl-3-[2-methyl-6-(trifluoromethyl)-3-pyridyl]thiourea] (Method 4).
  • 33
  • [ 383907-17-3 ]
  • (5S)-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-5-[3-[[2-methyl-6-(trifluoromethyl)-3-pyridyl]amino]-1,2,4-triazol-4-yl]-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C 2.1: air / dichloromethane / 1.5 h / 20 °C 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0 °C 3.2: 5.5 h / 0 °C 3.3: 16 h / 45 °C
  • 34
  • [ 383907-17-3 ]
  • (5S)-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-5-[[2-methyl-6-(trifluoromethyl)-3-pyridyl]carbamothioylamino]-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C 2: air / dichloromethane / 1.5 h / 20 °C
  • 35
  • [ 402479-93-0 ]
  • [ 383907-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / water; ethanol / 1 h / 100 °C 2: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 70 - 100 °C 3: ammonium formate; palladium 10% on activated carbon / ethanol / 0.67 h / 100 °C
  • 36
  • [ 261635-93-2 ]
  • [ 383907-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 70 - 100 °C 2: ammonium formate; palladium 10% on activated carbon / ethanol / 0.67 h / 100 °C
  • 37
  • benzyl 2-methyl-6-(trifluoromethyl)pyridin-3-ylcarbamate [ No CAS ]
  • [ 383907-17-3 ]
YieldReaction ConditionsOperation in experiment
95% With palladium 10% on activated carbon; ammonium formate In ethanol at 100℃; for 0.666667h; 2-Methyl 6-(trifluoromethyl)pyridin-3-amine Ammonium formiate mg) were added to a solution of benzyl 2-methyl-6-(trifluoromethyl)pyridin-3-ylcarbamate (1.01 g, 3.26 mmol) in EtOH (100 mL). The resulting mixture was heated at 100 °C for 40 minutes after which it was allowed to cool to rt. The reaction mixture was filtered through a small pad of Celite before it was concentrated. The residue was obtained in saturated NalTCCb aqueous solution (20 mL) and EtOAc (20 mL). The phases were separated and the water phase was extracted with EtOAc (2x20 mL). The combined organics were washed with brine (20 mL) and dried (MgS04). After filtration and evaporation the title compound (547 mg, 3.11 mmol, 95%) was assessed pure enough to be used directly in the next step. 1H-NMR (CDCb) d 7.35 (d, =8.4 Hz, 1H) 6.96 (d, =8.0 Hz, 1H) 3.94 (br s, 2H) 2.46 (s, 3H).
  • 38
  • [ 383907-17-3 ]
  • [ 140-89-6 ]
  • O-ethyl S-2-methyl-6-(trifluoromethyl)pyridin-3-yl carbonodithioate [ No CAS ]
  • 2-methyl-6-(trifluoromethyl)pyridin-3-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methyl-6-(trifluoromethyl)pyridin-3-amine With hydrogenchloride; sodium nitrite In water at 0℃; for 2h; Stage #2: potassium ethyl xanthogenate In water at 65℃; for 0.25h; -ethyl ,V-2-methyl-6-(tnfluoromethyl)pyndin-3-yl carbonodithioate A solution of sodium nitrite (216 mg, 3.14 mmol) in water (2 mL) was slowly added to a suspension of 2-methyl 6-(trifluoromethyl)pyridin-3-amine (500 mg, 2.84 mmol) in 2M HC1 aqueous solution (9.6 mL) and water (7.9 mL) at 0 °C. After two hours of stirring at 0 °C the bright yellow reaction mixture was added to a solution of potassium ethyl xanthate (547 mg, 3.41 mmol) in water (2 mL) at 65 °C. The resulting mixture was kept at this temperature for 15 minutes before it was allowed to cool to rt. The water phase was extracted with EtOAc (2x 10 mL), then neutralized with 1M NaOH aqueous solution and again extracted with EtOAc (2x 10 mL). Combined organics were washed with brine (10 mL) and dried (MgS04). After filtration and evaporation the crude material (659 mg) was purified by column chromatography (S1O2, petroleum ether/EtOAc 99/1) to give the title compound (180 mg, 0.64 mmol, 23%) as a yellow oil, together with considerable amounts of 2-methyl-6-(trifluoromethyl)pyridin-3 -thiol (299 mg, 1.06 mmol, 37%, yellow solid). NMR (CDCb) title compound d 7.95 (d, =8.0 Hz, 1H) 7.58 (d, =8.0 Hz, 1H) 4.64 (q, J=1.2 Hz, 2H) 2.73 (s, 3H) 1.37 (t, J=1.2 Hz, 3H).
  • 39
  • [ 383907-17-3 ]
  • 1-(5-(trifluoromethyl)-1H-pyrazolo[4,3-b]pyridin-1-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: potassium acetate; acetic anhydride / toluene / 16 h / 80 °C
  • 40
  • [ 383907-17-3 ]
  • 3-bromo-5-(trifluoromethyl)-1H-pyrazolo[4,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: potassium acetate; acetic anhydride / toluene / 16 h / 80 °C 3: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 4: bromine / methanol; water / 1 h / 0 °C
  • 41
  • [ 383907-17-3 ]
  • [ 75-36-5 ]
  • [ 1383735-00-9 ]
YieldReaction ConditionsOperation in experiment
43% With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; 116.2 Step 2: iV-(2-methyl-6-(trifluoromethyl)pyridin-3-yl)acetamide. To a solution of 2- methyl-6-(trifluoromethyl)pyridin-3-amine (7.6 g, 43 mol) and triethylamine (13.1 g, 129 mmol) in THF (100 mL) was added AcCl (6.8 g, 86 mmol) dropwise at 0 °C under nitrogen atmosphere. The resulting solution was stirred at room temperature for 2 h. General Workup Procedure followed by Chromatography A afforded the title compound (4.1 g, 43%). MS (ESI) calc’d for (C9H9F3N2O) [M+H]+, 219.1; found, 219.0.
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