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[ CAS No. 1196153-82-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1196153-82-8
Chemical Structure| 1196153-82-8
Chemical Structure| 1196153-82-8
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Product Details of [ 1196153-82-8 ]

CAS No. :1196153-82-8 MDL No. :MFCD13189822
Formula : C6H5F3N2O Boiling Point : -
Linear Structure Formula :- InChI Key :HGRBXDHMWGUDPV-UHFFFAOYSA-N
M.W : 178.11 Pubchem ID :57347020
Synonyms :

Calculated chemistry of [ 1196153-82-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.67
TPSA : 59.14 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) : -6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.87
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 0.31
Log Po/w (SILICOS-IT) : 1.21
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.71
Solubility : 3.44 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (Ali) : -1.56
Solubility : 4.89 mg/ml ; 0.0275 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.98
Solubility : 1.89 mg/ml ; 0.0106 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 1196153-82-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1196153-82-8 ]

* 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 [ 1196153-82-8 ]

[ 1196153-82-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 216394-05-7 ]
  • [ 1196153-82-8 ]
  • [ 1638200-93-7 ]
YieldReaction ConditionsOperation in experiment
12% With pyridine; dmap at 0 - 20℃; for 1h; 128 5-bromo-6-chloro-N-[4-hydroxy-6-(trifluoromethyl)pyridiii-3-yl]pyridine-3- sulfonamide To a stirred solution of 5-amino-2-(trifiuoromethyl)pyridin-4-ol (130 mg, 0.73 mmol) and N,N-dimethylpyridin-4-amine (4.4 mg, 0.036 mmol) in pyridine (1.5 mL) at 0°C was added 5-bromo-6-chloropyridine-3-sulfonyl chloride (220 mg, 0.759 mmol). The reaction mixture was stirred at room temperture for 1 hr. More 5-bromo-6-chloropyridine-3- sulfonyl chloride (26 mg, 0.091 mmol) was added and stirring continued for a further 1 hr. The pH was adjusted to 3 with 1 M HC1, the mixture extracted with EtOAc (3x 1 OmL) and the organics combined, dried (MgSC^), filtered and the filtrate concentrated to dryness. The crude material was purified by automated reverse phase HPLC (low pH method) to yield the title compound as an off white solid (36 mg, 12%).
  • 2
  • [ 438554-44-0 ]
  • [ 1196153-82-8 ]
YieldReaction ConditionsOperation in experiment
85% With water; iron; ammonium chloride In methanol at 80℃; 5-amino-2-(trifluoromethyl)pyridine-4-ol To a stirred solution of 5-nitro-2-(trifluoromethyl)pyridin-4-ol, made by a literature method (U.S. 7767687, 2010) (720 mg, 3.46 mmol) in MeOH (5 mL) at room temperature was added ammonium chloride (925 mg, 17.3 mmol) in water (25 mL). Iron powder (966 mg, 17.3 mmol) was then added to the stirred suspension and the reaction heated at 80°C overnight. The solvent was removed and the residual crude solid sonicated sequentially with dichloromethane (20 mL) then 1 : 1 CHCI3/ propan-2-ol (30 mL). The combined solutions were evaporated to give the title compound as a brown solid (528 mg, 85%); 'H NMR (500 MHz, DMSO-d6) δ 5.31 (s, 2H), 6.99 (s, 1H), 7.88 (s, 1H), 10.81 (s, 1H).
70% With platinum(IV) oxide; hydrogen In ethanol for 1.5h; 400 Preparation 400
5-amino-2-(trifluoromethyl)pyridin-4-ol
300 mg of 5-nitrol-2-(trifluoromethyl)pyridin-4-ol (1.44 mmol; 1.00 eq) were diluted in 3 mL of EtOH. 35 mg of platinum oxide hydrate (0.14 mmol; 0.10 eq) were added under nitrogen then the reaction medium was stirred at RT under hydrogen atmospheric pressure for 1 h 30. The suspension was filtered on celite and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography on silica using a DCM/0% to 5% EtOH eluent, to give 230 mg of the title compound in the form of a violet oil. Yld: 70%. 1H NMR (300 MHz, DMSO-d6) δppm 6.99 (s, 1H) 7.89 (s, 1H). LC-MS: m/z (M+)+: 178.
With iron; ammonium chloride at 90℃; for 1h; 5-Ami no-2-(tritl uoromethyl)pyridi n-4-ol To a solution of 5-nitro-2-(trifluoromethyl)pyridin-4-ol (2.2g, 10.5mmol) were added ammonium chloride (2.9g, 52.8mmol), Fe powder (2.9g, 52.8mmol) and water (3mL). The reaction mixture was stirred at 90 00 for lh. The TLC showed reaction to be complete. Reaction mixture was cooled to room temperature and filtered through a celite bed. The filtrate was concentrated, diluted with water (25mL) and extracted with EtOAc (3x5OmL). The organics were dried (Na2504), filtered and concentrated under reduced pressure to afford 5-am ino-2-(trifluoromethyl)pyridin-4- 01 as a brown liquid. Yield: 890mg (crude); MS (ESl+) for CHNOS m/z 179.01 [M+H].
  • 3
  • [ 478264-00-5 ]
  • 5-amino-2-(trifluoromethyl)pyridine-4-ol [ No CAS ]
  • N-[4-hydroxy-6-(trifluoromethyl)pyridin-3-yl]-6-methylpyridine-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With pyridine at 80℃; for 1h; 132 N-[4-hydroxy-6-(trifluoromethyl)pyridiii-3-yl]-6-methylpyridine-3-sulfonamide To a stirred solution of 5-amino-2-(trifiuoromethyl)pyridin-4-ol (150 mg at 50% purity, 0.421 mrnol ) in pyridine at 80°C was added 6-methylpyridine-3-sulfonyl chloride (prepared according to a method described in WO 2007/023186 Al), 55 mg, 0.29 mmol). The mixture was stirred for 1 hr at this temperature then the pyridine was evaporated. The residue was purified by low pH automated preparative HPLC to afford the title compound as a white solid (10 mg, 7%).
  • 4
  • [ 1196153-82-8 ]
  • [ 1638201-02-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; dmap / 1 h / 0 - 20 °C 2: tetrahydrofuran / 5 h / 60 °C
  • 5
  • [ 1196153-82-8 ]
  • [ 2126740-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 24 h / 65 °C 2: dmap; pyridine / 18 h / 0 - 20 °C / Inert atmosphere
  • 6
  • 5-amino-2-(trifluoromethyl)pyridine-4-ol [ No CAS ]
  • [ 104619-51-4 ]
  • 6-(trifluoromethyl)oxazolo[4,5-c]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In tetrahydrofuran; at 65℃; for 24h; 6-(trifluoromethyl)oxazolo[4,5-c]pyridin-2-amine 5-amino-2-(trifluoromethyl)pyridine-4-ol (220 mg, 1.24 mmol) was dissolved in anhydrous THF (7 mL). Di(1H-imidazol-1-yl)methanimine was then dissolved into the solution. The reaction was stirred at 65 C. for 24 hours. After cooling the solution to room temperature, the solution was taken up in ethyl acetate and washed with deionized water, saturated NH4Cl, and saturated NaCl. The organic layer was dried over MgSO4, filtered, and concentrated down to the crude material. Excess CH2Cl2 was added to the crude solid, which precipitated out. The pure solid was filtered and dried under vacuum. Yield: 91%. 1H NMR (400 MHz, DMSO): 8.58 (s, 1H), 8.17 (s, 2H), 8.02 (s, 1H). [M+1]+=204.1.
  • 7
  • [ 1196153-82-8 ]
  • [ 2191445-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 4 h / 110 °C 2: N,N-dimethyl-formamide; thionyl chloride / 4 h / 80 °C 3: caesium carbonate / N,N-dimethyl-formamide / 20 °C
  • 8
  • [ 1196153-82-8 ]
  • [ 2191446-20-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 4 h / 110 °C 2: N,N-dimethyl-formamide; thionyl chloride / 4 h / 80 °C
  • 9
  • [ 506-68-3 ]
  • [ 1196153-82-8 ]
  • [ 2126740-48-3 ]
YieldReaction ConditionsOperation in experiment
In water at 100℃; for 0.5h; 6-(Tritl uoromethyl)oxazolo[4,5-c]pyridi n-2-amine To a solution of 5-amino-2-(trifluoromethyl)pyridin-4-ol (500mg, 2.8Ommol) in H20 (5mL) was added cyanogen bromide (442mg, 4.2lmmol) at rt in portions. The resulting mixture was stirred at 100 °C for 30 mm. The TLC showed reaction to be complete. The mixture was allowed to cool to room temperature, basified with aq NaHCO3 solution and extracted with EtOAc (3X25mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to afford 6- (trifluoromethyl)oxazolo[4,5-c]pyridin-2-amine as a brown solid. Yield: 510 (89%); 1H NMR (400 MHz, DMSO-d6): 8.58 (5, 1H), 8.16 (bs, 2H), 8.02 (5, 1H); MS (ESl+) for CHNOS m/z 202.23 [M-H].
  • 10
  • [ 1196153-82-8 ]
  • [ CAS Unavailable ]
  • [ 2191446-19-0 ]
YieldReaction ConditionsOperation in experiment
1.1 g With pyridine at 110℃; for 4h; 6-(Tritluoromethyl)oxazolo[4,5-c]pyridine-2-thiol To a solution of 5-amino-2-(trifluoromethyl)pyridin-4-ol (2.Og, 11.2mmol) in pyridine (2OmL) was added potassium ethyl xanthate (2.2g, 13.4mmol) at rt. The reaction mixture was stirred at 110 00 for 4h. The TLC showed reaction to be complete. Reaction mixture was cooled to rt and acidified to pH 4-5 by slow addition of iON HCI. The reaction mixture was extracted with EtOAC (3X25mL). The organics were dried (Na2504), filtered and concentrated under reduced pressure. The residue was trituratedwith Et20 (25m L) to give 6-(trifluoromethyl)oxazolo[4, 5-c]pyridine-2-thiol as a brown solid. Yield: 1.lg (50%); 1H NMR (400 MHz, DMSO-d6): 8.63 (5, 1H), 8.20 (5, 1 H); MS (ESl+) for CHNOS m/z 220.93 [M+H].
  • 11
  • [ 170886-13-2 ]
  • 5-amino-2-(trifluoromethyl)pyridine-4-ol [ No CAS ]
  • 12
  • [ 1196153-82-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3 / acetonitrile / 1 h / 20 °C 2: sodium tetrahydridoborate / water monomer; ethanol / 1.5 h / 90 °C
  • 13
  • [ 1196153-82-8 ]
  • [ 2758260-49-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3 / acetonitrile / 1 h / 20 °C 2: tetrahydrofuran; diethyl ether / 0.75 h / -10 - 20 °C
  • 14
  • [ 1196153-82-8 ]
  • [ 2758257-88-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3 / acetonitrile / 1 h / 20 °C 2: tetrahydrofuran; diethyl ether / 0.75 h / -10 - 20 °C 3: sodium iodide; chloro-trimethyl-silane / acetonitrile / 1.5 h / 60 °C
  • 15
  • [ 1196153-82-8 ]
  • [ 2758260-72-7 ]
  • [ 2758260-37-4 ]
YieldReaction ConditionsOperation in experiment
70% With Cs2CO3 In acetonitrile at 20℃; for 1h; 275.a a) 3-(5,6-Dimethoxypyrazin-2-yl)-7-(trifluoromethyl)-3,4-dihydro-2H-pyrido[4,3- b][1,4]oxazine A (5,6-dimethoxypyrazin-2-yl)ethan-1-one (586 mg, 2.25 mmol) and cesium carbonate (732 mg, 2.25 mmol) in acetonitrile (10 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated onto silica and purified by flash column chromatography (0-100% ethyl acetate in dichloromethane) to yield the title compound as part of a mixture as a gummy yellow solid (536 mg, 70%). To a solution of 3-(5,6-dimethoxypyrazin-2-yl)-7-(trifluoromethyl)-2H-pyrido[4,3-b][1,4]oxazine (200 mg, 0.588 mmol) in ethanol (7 mL) and water (2.1 mL) at room temperature was added sodium borohydride (44 mg, 1.18 mmol) and stirred at 90 °C for 90 min. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, concentrated onto silica and purified by flash column chromatography (0-40% 3:1 ethyl acetate and ethanol in cyclohexane) to yield the title compound as a yellow solid (136 mg, 67%). H NMR (400 MHz, CDCl3): δ 8.09 (s, 1 H), 7.66 (s, 1 H), 7.12 (s, 1 H), 4.60-4.49 (m, 3 H), 4.35-4.30 (m, 1 H), 4.02 (s, 3 H), 4.00 (s, 3 H).
70% With Cs2CO3 In acetonitrile at 20℃; for 1h; 275.a a) 3-(5,6-Dimethoxypyrazin-2-yl)-7-(trifluoromethyl)-3,4-dihydro-2H-pyrido[4,3- b][1,4]oxazine A (5,6-dimethoxypyrazin-2-yl)ethan-1-one (586 mg, 2.25 mmol) and cesium carbonate (732 mg, 2.25 mmol) in acetonitrile (10 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated onto silica and purified by flash column chromatography (0-100% ethyl acetate in dichloromethane) to yield the title compound as part of a mixture as a gummy yellow solid (536 mg, 70%). To a solution of 3-(5,6-dimethoxypyrazin-2-yl)-7-(trifluoromethyl)-2H-pyrido[4,3-b][1,4]oxazine (200 mg, 0.588 mmol) in ethanol (7 mL) and water (2.1 mL) at room temperature was added sodium borohydride (44 mg, 1.18 mmol) and stirred at 90 °C for 90 min. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, concentrated onto silica and purified by flash column chromatography (0-40% 3:1 ethyl acetate and ethanol in cyclohexane) to yield the title compound as a yellow solid (136 mg, 67%). H NMR (400 MHz, CDCl3): δ 8.09 (s, 1 H), 7.66 (s, 1 H), 7.12 (s, 1 H), 4.60-4.49 (m, 3 H), 4.35-4.30 (m, 1 H), 4.02 (s, 3 H), 4.00 (s, 3 H).
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