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[ CAS No. 99368-66-8 ] {[proInfo.proName]}

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Chemical Structure| 99368-66-8
Chemical Structure| 99368-66-8
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Product Details of [ 99368-66-8 ]

CAS No. :99368-66-8 MDL No. :MFCD00276983
Formula : C6H3F3N2O3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :BHUILUYFGJBXHQ-UHFFFAOYSA-N
M.W : 208.09 Pubchem ID :2775095
Synonyms :

Calculated chemistry of [ 99368-66-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.08
TPSA : 78.94 ?2

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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.95
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : -0.15
Consensus Log Po/w : 1.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.29
Solubility : 1.08 mg/ml ; 0.00518 mol/l
Class : Soluble
Log S (Ali) : -2.81
Solubility : 0.325 mg/ml ; 0.00156 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.72
Solubility : 3.93 mg/ml ; 0.0189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 99368-66-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 99368-66-8 ]

* 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 [ 99368-66-8 ]

[ 99368-66-8 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 99368-66-8 ]
  • [ 99368-67-9 ]
YieldReaction ConditionsOperation in experiment
96% With phosphorus pentachloride; trichlorophosphate; at 110 - 120℃; for 8.0h; a mixture of 5-nitro-3- (trifluoromethyl) pyridine -2 (1H) -One, 3 (1.50g, 7.21mmol), POCl3 (2.76g, 18.02mmol) and PCl5(1.4g, 10. 09mmol) was heated 8 hours to about 110 ~ 120 and poured into ice water. Themixture was neutralized with solid NaHCO3, and extracted with ethylacetate (3 × 40ml). The organic phases were combined, dried over Na2SO4,all solvents were evaporated under reduced pressure to give 2-chloro-5-nitro-3-(trifluoromethyl) pyridine 4.
96% With phosphorus pentachloride; trichlorophosphate; at 110 - 120℃; for 8.0h; Synthesis of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine, 4 (0076) (0077) A mixture of 5-nitro-3-(trifluoromethyl)pyridin-2(1H)-one 3 (1.50 g, 7.21 mmol), POCl3 (2.76 g, 18.02 mmol) and PCl5 (1.4 g, 10.09 mmol) is heated to about 110-120° C. for 8 hours and then poured into ice water. The mixture is neutralized with solid NaHCO3 and extracted with ethyl acetate (3×40 ml). The combined organic phases is dried over Na2SO4 and all solvents removed under reduced pressure to obtain 2-chloro-5-nitro-3-(trifluoromethyl)pyridine 4.
With thionyl chloride; 5-Nitro-3-(trifluoromethyl)pyridin-2(1H)-one was treated with thionyl chloride and then the resulting 2-chloro-5-nitro-3-(trifluoromethyl)pyridine was treated with dimethylamine to obtain N,N-dimethyl-5-nitro-3-(trifluoromethyl)pyridin-2-amine.
  • 2
  • [ 280-57-9 ]
  • [ 99368-66-8 ]
  • [ 4285-42-1 ]
  • [ 548766-55-8 ]
YieldReaction ConditionsOperation in experiment
92% In tetrahydrofuran; Example 257 Methyl-phenyl-carbamic Acid 5-nitro-3-trifluoromethyl-pyridin-2-yl Ester A solution of <strong>[99368-66-8]2-hydroxy-5-nitro-3-(trifluoromethyl)pyridine</strong> (0.36 g, 1.73 mmol), N-methyl-N-phenylcarbamoyl chloride (0.44 g, 2.59 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.29 g, 2.59 mmol) in tetrahydrofuran (15 ml) was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (15:85)) yielding the title compound (0.55 g, 92% yield) as an orange solid. 1H NMR (300 MHz, CDCl3): delta 3.46 (br.s, 3H), 7.23-7.46 (m, 5H), 8.70 (br.s, 1H), 9.37 (br.s, 1H); HPLC-MS (Method A): m/z=364 (M+H); Rt=4.08 min.
  • 3
  • [ 22245-83-6 ]
  • [ 99368-66-8 ]
YieldReaction ConditionsOperation in experiment
94% With sulfuric acid; nitric acid; at -10 - 40℃; for 6h; The HNO3 (24 mL, 0.55 mol) was dropped solwly at -10 C to a solution of 2-hydroxyl-3- (trifluoromethyl)pyridine 5 (20.00 g,0.12 mol) in H2SO4 (160 mL). The reaction mixture was stirred at 40 C for 6 h and TLC analysis indicated the reactionwas completed.The reaction mixture was added into ice water. Then the solutionwas adjusted pH being 4-5 with saturated aqueous NaOH andextracted with EtOAc. The organic phase was washed with saturatedbrine, dried over Na2SO4, filtered and concentrated underreduced pressure to give the corresponding product. It was obtainedas a light yellow solid in 94% yield. 6 was ready for the nextstep without the further purification. HRMS (ESI): m/z, calcd forC6H4F3N2O3 [M H], 209.0169; found: 209.0171.
78% With sulfuric acid; nitric acid; at 60℃; for 21.5h;Cooling with ice; To an ice-cooled solution of 3-(trifluoromethyl)pyridin-2-ol (5 g, 30.7 mmol) in H2SO4 (30 mL, 563 mmol) was added nitric acid (1.507 mL, 33.7 mmol) dropwise. After 30 min, the ice bath was removed and the reaction mixture was stirred at 25 C for 16 h. The reaction mixture was warmed to 60 C for 5 h, cooled, and added to 150 g of ice. The resulting precipitate was collected by filtration, rinsed with additional H20, and air-dried to afford the first batch of product. Another crop of product was obtained after evaporating the mother liquor to less than 100 mL, cooling on an ice bath, and adding NaOH to adjust to pH 8. The mixture was extracted by EA (100 mL). The organic layer was dried and concentrated to give the product, which was combined with the first batch to yield a yellow solid of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (5 g, 24.03 mmol, 78.0% yield): NMR (400 MHz, CD3OD) delta 8.85 (d, J= 3.2 Hz, 1H), 8.58 (d, J= 2.8 Hz, 1H).
74.5% With sulfuric acid; nitric acid; at 20℃; for 4h;Cooling with ice; In an ice bath, 2-hydroxy-3-trifluoromethylpyridine (25 g, 0.15 mol) was added into cold concentrated sulthric acid (150 ml), followed by drop wise addition of concentrated nitric acid (58 ml). The reaction mixture was warmed to room temperature and was stirred at room temperature for 4 h, and the reaction mixture was poured into 1 liter of icy water to afford white solids. The solids were filtered off and washed with water twice and dried to afford the first batch of compound 2 (16.97 g). The filtrate was adjusted to weak acidic by 1 OM sodium hydroxide, and the solution was extracted by200 ml ethyl acetate for three times. The combined organic phases were dried over anhydrous sodium sulfate, and thesolvent was removed. The residue was purified by columnchromatography (mobile phase, DCMJMeOH) to give the second batch of compound 2 (6.81 g). Total yield was 74.5%.
74% With sulfuric acid; nitric acid; at 20℃; To a solution of compound 1 (25g, 0.15mol) in cocnH2SO4 (100ml) was added the mixture HNO3 and cocnH2SO4 (v/v=1/1)(100ml) drop-wise at room temperature. The reaction mixture was stirred for 4h. This reaction mixture was added into ice (1kg) portion-wise, stirred for 2h, filtrated, washed with water (50ml), then, dried to afford 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2) (23.3g, 74%). 1H NMR (400 MHz, DMSO-d6) delta 13.49 (br, 1H), 8.97 (s, 1H), 8.47 (s, 1H). 13C NMR (101 MHz, DMSO-d6) delta 158.0, 142.4, 134.1 (q, J =5.1Hz), 128.7, 121.9 (q, J = 272.7 Hz), 116.8 (q, J = 30.3 Hz).
73.3% With sulfuric acid; nitric acid; at 0 - 60℃; for 21h; To a mixture of 3- (trifluoromethyl) pyridin-2-ol (2 g 12.26 mmol) was added nitric acid (1.644 mL 36.8 mmol) and H2SO4(12.03 g 123 mmol) at 0 . Then the mixture was stirred at 25 for 16 h. The mixture was then warmed to 60 for 5 h cooled and added to 150 g of ice. The mixture was extracted with EA (2 x 100 mL) and washed with H2O (100 mL) to give the organic layer. The combined organic extract was washed with brine dried over Na2SO4 concentrated to yield a brown solid of 5-nitro-3- (trifluoromethyl) pyridin-2-ol (2.2 g 8.99 mmol 73.3yield) 1HNMR(400 MHz CD3OD) delta 8.91 (d J 2.43 Hz 1H) 9.42 (d J 2.43 Hz 1H) ES-LCMS m/z 209.0 (M+H)
69% Reference Example 117 5-nitro-3-(trifluoromethyl)pyridin-2-ol; 2-Hydroxy-3-(trifluoromethyl)pyridine (3.0 g) was added to conc. sulfuric acid (18 mL) under ice-cooling, and the mixture was stirred at the same temperature for 5 min. Fuming nitric acid (90-95%, 7 mL) was added dropwise over 5 min, and the mixture was allowed to return to room temperature over 2 hr, heated to 50 C. and stirred for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice (200 g), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was washed with diisopropyl ether to give the title compound as a solid (yield 2.7 g, 69%). 1H-NMR (CDCl3) delta: 8.65-8.67 (1H, m), 8.80-8.81 (1H, m), 1H not detected.
51.5% With sulfuric acid; nitric acid; at 26℃; for 10.5h;Cooling with ice; To an ice-cooled solution of 3-(trifluoromethyl)pyridin-2-ol (4 g, 24.53 mmol) in H2SO4 (26.1 mL, 491 mmol) was added nitric acid (1.206 mL, 27.0 mmol) dropwise. After 30 min, the ice bath was removed and the reaction was stirred at 26 C. for 10 h. The reaction mixture was added to 120 g ice. The resulting precipitate was collected by filtration, rinsed with additional H2O and air-dried to afford the first batch of product. Another crop of product was obtained after evaporating the mother liquor to less than 100 mL, cooling on an ice bath, and adding NaOH to adjust to pH=8. The mixture was extracted by EA (100 mL). The organic layer was dried and concentrated to give the product, which was combined with the first batch to yield a yellow solid of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2.63 g, 12.64 mmol, 51.5% yield): 1H NMR (400 MHz, CD3OD) delta: 8.86 (d, J=3.1 Hz, 1H), 8.55 (d, J=2.6 Hz, 1H); ES-LCMS m/z 209.0 (M+H).
With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 3h; 3. 5-Nitro-3-trifluoromethyl-pyridin-2-ol To 3-trifluoromethyl-pyridin-2-ol (1.63 g, 10 mmol) in concentrated sulfuric acid at O0C, add dropwise fuming nitric acid (2 mL). Stir the mixture at room temperature for 3 hours and pour onto ice. Collect the precipitate by filtration, air-dry and finally dry in a vacuum oven overnight to give the title compound as a white solid
EXAMPLE 26; 3-(4-tert-Butyl-phenyl)-N-(6-imidazol-1-yl-5-trifluoromethyl-pyridin-3-yl)-propionamide (Cpd 202) A. To an ice-cooled solution of compound 26a (5.93 g, 36.4 mmol) in 35 mL concentrated H2SO4 was added concentrated HNO3 (2.6 mL, 40.8 mmol) dropwise. After 30 minutes the ice bath was removed and the reaction was stirred at ambient temperature for 15 hours. The reaction mixture was then warmed to 60 C for 5 hours, cooled, and added to 150 g of ice. The resulting precipitate was collected by filtration, rinsed with additional water, and air-dried to afford the first batch of product. Another crop of product was obtained after evaporating the mother liquor to less than 100 mL volume, cooling on an ice bath, and adding NaOH (25.34 g). This solid was filtered off, rinsed with water, and air-dried to provide another batch of product of compound 26b. 1H NMR (d6-DMSO): delta 13.49 (br s, 1H), 8.96 (s, 1H), 8.47 (s, 1H).

  • 4
  • [ 99368-66-8 ]
  • [ 99368-67-9 ]
YieldReaction ConditionsOperation in experiment
86% With thionyl chloride; In N,N-dimethyl-formamide; at 100℃; for 10.0h; SOCl2 (18.45 mL, 253 mmol) was added to a solution of <strong>[99368-66-8]5-nitro-3-(trifluoromethyl)pyridin-2-ol</strong> (2.63 g, 12.64 mmol). DMF (1.957 mL, 25.3 mmol) was added and the mixture was at 100 C. for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (2.46 g, 10.86 mmol, 86% yield) was used in the next step without further purification. TLC (PE/EA=5:1, Rf=0.6): 1H NMR (400 MHz, CDCl3) delta: 9.23-9.59 (m, 1H), 8.79 (d, J=2.4 Hz, 1H).
86% With thionyl chloride; N,N-dimethyl-formamide; at 100℃; for 10.0h; SOCl2 (18.45 mL, 253 mmol) was added to a solution of 5 -nitro-3 -(trifluoromethyl)pyridin-2-ol (2.63 g, 12.64 mmol). DMF (1.957 mL, 25.3 mmol) was added and the mixture was at 100 C for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCC>3 solution. The combined organic extract was washed with brine, dried over MgSO/i, filtered and concentrated. The resulting 2-chloro-5 -nitro-3 -(trifluoromethyl)pyridine (2.46 g, 10.86 mmol, 86% yield) was used in the next step without further purification. TLC (PE/EA = 5: 1, Rf = 0.6): 'HNMR (400 MHz, CDCI3) delta: 9.23-9.59 (m, 1H), 8.79 (d, J = 2.4 Hz, 1H).
77% With phosphorus pentachloride; trichlorophosphate; at 90℃; for 3.0h; Reference Example 118 2-chloro-5-nitro-3-(trifluoromethyl)pyridine; A mixture of <strong>[99368-66-8]5-nitro-3-(trifluoromethyl)pyridin-2-ol</strong> (2.65 g), phosphorus pentachloride (3.17 g) and phosphorus oxychloride (1.5 mL) was stirred at 90 C. for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1?3:1) to give the title compound as a yellow oil (yield 2.21 g, 77%). 1H-NMR (CDCl3) delta: 8.79-8.81 (1H, m), 9.40-9.41 (1H, m).
55.1% With thionyl chloride; N,N-dimethyl-formamide; at 80℃; for 16.0h; To a mixture of 5-nitro-3- (trifluoromethyl) pyridin-2-ol (2 g 9.61 mmol) was added SOCl2(21.04 mL 288 mmol) and DMF (0.074 mL 0.961 mmol) . Then the mixture was stirred at 80 for 16 h. The mixture was concentrated and extracted with EA (2 x 100 mL) and washed with H2O (100 mL) to give the organic layer. The combined organic extract was washed with brine dried over Na2SO4 concentrated to yield a brown solid of 2-chloro-5-nitro-3- (trifluoromethyl) pyridine (2 g 5.30 mmol 55.1yield) 1HNMR(400 MHz CD3OD) delta 8.91 (d J 2.43 Hz 1H) 9.42 (d J 2.43 Hz 1H)
With trichlorophosphate; at 85℃; for 18.0h; 4. 2-ChlotauO-5-nitro-3-trifluoromethyl-pyridine Heat a mixture of <strong>[99368-66-8]5-nitro-3-trifluoromethyl-pyridin-2-ol</strong> (416 mg, 2.0 mmol) and phosphorus oxychloride (1 mL) at 85C for 18 hours. Cool the mixture and remove the volatiles by rotary evaporation. Dissolve the residue in EtOAc (15 mL) and wash with water (10 mL), saturatedNaHCO3(aq) (10 mL) and brine (10 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure to yield the title compound.
With thionyl chloride; In N,N-dimethyl-formamide; for 4.0h;Heating / reflux; B. To a mixture of compound 26b (3.84 g, 18.5 mmol) in 20 mL SOCl2 was added 0.5 mL DMF. The mixture was heated to reflux for 4 hours then concentrated in vacuo. The residue was dissolved in benzene and concentrated again in vacuo. This residue was taken up in 50 mL EtOAc and washed with 50 mL saturated NaHCO3, and 50 mL brine, then dried over Na2SO4, and filtered and concentrated in vacuo. The resulting residue was chromatographed over silica gel (0-10% EtOAc/heptane) to give compound 26c as a pale yellow oil. 1H NMR (d6-DMSO): delta 9.52 (s, 1H), 8.92 (s, 1H).
With phosphorus pentachloride; trichlorophosphate; at 90℃; for 3.0h; (0874) A mixture of Compound 288A (1.69 g), phosphorus pentachloride (2.03 g), and phosphoryl trichloride (0.97 ml) was heated at 90° C. for 3 hours. After cooling, the reaction mixture was poured into ice, and extracted with ethyl acetate three times. The extract was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with 10percent ethyl acetate in hexanes to provide the title compound.

  • 5
  • [ 99368-66-8 ]
  • 2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile [ No CAS ]
  • 6
  • [ 99368-66-8 ]
  • tert-butyl 2-cyano-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetate [ No CAS ]
  • 8
  • [ 99368-66-8 ]
  • 2-ethoxy-5-nitro-3-(trifluoromethyl)pyridine [ No CAS ]
  • 9
  • [ 99368-66-8 ]
  • 6-ethoxy-5-(trifluoromethyl)pyridin-3-amine [ No CAS ]
  • 10
  • [ 99368-66-8 ]
  • 2-(4-bromo-2-fluorophenyl)-N-(6-ethoxy-5-(trifluoromethyl)pyridin-3-yl)acetamide [ No CAS ]
  • 11
  • [ 99368-66-8 ]
  • N-(6-ethoxy-5-(trifluoromethyl)pyridin-3-yl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide [ No CAS ]
  • 12
  • [ 99368-66-8 ]
  • N,N-dimethyl-2-((5-nitro-3-(trifluoromethyl)pyridin-2-yl)oxy)ethanamine [ No CAS ]
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; ;