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[ CAS No. 1805523-36-7 ] {[proInfo.proName]}

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Chemical Structure| 1805523-36-7
Chemical Structure| 1805523-36-7
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Product Details of [ 1805523-36-7 ]

CAS No. :1805523-36-7 MDL No. :MFCD22490610
Formula : C8H5BrF2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VZZHRHDBHLFPBY-UHFFFAOYSA-N
M.W : 251.02 Pubchem ID :75487922
Synonyms :

Calculated chemistry of [ 1805523-36-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.34
TPSA : 26.3 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 3.35
Log Po/w (MLOGP) : 3.5
Log Po/w (SILICOS-IT) : 3.23
Consensus Log Po/w : 2.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.29
Solubility : 0.129 mg/ml ; 0.000515 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.335 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.89
Solubility : 0.0323 mg/ml ; 0.000129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.77

Safety of [ 1805523-36-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1805523-36-7 ]

* 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 [ 1805523-36-7 ]

[ 1805523-36-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 67-56-1 ]
  • [ 170108-05-1 ]
  • C8H5BrF2O2 [ No CAS ]
  • 2
  • [ 1805523-36-7 ]
  • [ 2222438-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate / 1,2-dimethoxyethane / 12 h / 80 °C / Inert atmosphere; Schlenk technique 2: potassium hydroxide / methanol / Inert atmosphere; Schlenk technique
  • 3
  • [ 1805523-36-7 ]
  • [ 98-80-6 ]
  • [ 2227345-43-7 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate In 1,2-dimethoxyethane at 80℃; for 12h; Inert atmosphere; Schlenk technique;
  • 4
  • [ 1805523-36-7 ]
  • [ 2271185-91-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; cesium fluoride; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 2 h / 20 °C
  • 5
  • [ 1805523-36-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; cesium fluoride; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 2 h / 20 °C 3: triphenylphosphine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 70 °C
  • 6
  • [ 1805523-36-7 ]
  • [ 153435-63-3 ]
  • [ 2271185-90-9 ]
YieldReaction ConditionsOperation in experiment
16 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere; 1 Step 1: To a mixture of A-8.1 (32.0 g, 0.127 mol), A-8.2 (51.76 g, 0.140 mol), CsF (40.42 g,0.268 mol) and Cul (2.46 g, 0.013 mol) in DMF (400 mL) is added Pd(PPh3)4 (15.0 g, 0.013 mol)under a nitrogen atmosphere. The mixture is heated at 120 00 for 16 h. The reaction mixture is poured into NH4CI (aq. Solution, 2.0 L) and extracted with EA): The organic layer is dried and concentrated to give the crude product which is purified by flash column chromatography on silica gel (using petroleum ether/EA 10/1 - 1/1) to provide 16.0 g of A-8.3. TLC (Rf): 0.5 (silicagel; petroleum ether/EA 2/1)
  • 7
  • [ 1805523-36-7 ]
  • [ CAS Unavailable ]
  • [ 2711860-00-1 ]
YieldReaction ConditionsOperation in experiment
3.27 g With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; Synthesis of methyl 2-bromo-3-fluoro-4-((2S)-2-((tetrahydro-2H-pyran-2- yl)oxy)propoxy)benzoate (N-XXVIII) At 0°C NaH (0.704 g, 17.6 mmol, 60% in mineral oil) was added portionwise to a stirred solution of (2S)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol (N-XIII-b) (2.60 g, 16.25 mmol) in DMF (50 ml_). Then, methyl 2-bromo-3,4-difluorobenzoate (3.4 g, 13.5 mmol) was added and the reaction mixture was stirred for 2 h at 0°C. The reaction mixture was quenched with a sat solution of NH4CI and extracted with EtOAc. The organic phases were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash chromatography (silica, hexane/EtOAc 2:1) to afford the title compound (3.27 g) as a beige oil. UPLC-MS 1 : m/z 408.2 / 410.2 [M+NH4]+, tR = 1.24 min.
  • 8
  • [ 1805523-36-7 ]
  • [ 1805552-00-4 ]
YieldReaction ConditionsOperation in experiment
92% With acetylhydroxamic acid; potassium carbonate In dimethyl sulfoxide at 80℃; for 2h; Sealed tube; 60.1 Step 1: Methyl 2-bromo-3-fluoro-4-hydroxybenzoate To a screw-cap vial were added N-hydroxyacetamide (5.38 g, 71.7 mmol), K2CO3 (16.52 g, 120.0 mmol), methyl 2-bromo-3,4-difluorobenzoate (6.0 g, 23.90 mmol) and DMSO (20.0 mL). The vessel was sealed and heated at 80 °C for 2 h and monitored for conversion by TLC. The reaction mixture was cooled to rt and quenched with approximately 9 equiv. of 2M HCL to a final pH of approximately 3-6. The aqueous phase was extracted with ethyl acetate (2 x 100.0 mL). The combined organic layer was washed with water (20.0 mL), brine (20.0 mL), dried over sodium sulphate and evaporated under reduced pressure to get the crude product. The crude product was purified by flash chromatography with 40% ethyl acetate in n-hexane as the eluent to afford the titled compound (5.5 g, 92.0 % yield) as white solid. MS (ES+) m/z = 247.14 (M -2) (-ve mode)
  • 9
  • [ 1805523-36-7 ]
  • [ 2660189-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetylhydroxamic acid; potassium carbonate / dimethyl sulfoxide / 2 h / 80 °C / Sealed tube 2: nitroperoxous acid potassium salt; sulfuric acid / 1.67 h / 0 °C
  • 10
  • [ 1805523-36-7 ]
  • [ 2839672-14-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide; acetonitrile / 10 h / 70 °C 2: triethylsilane; palladium diacetate; tricyclohexylphosphine; sodium carbonate / N,N-dimethyl-formamide / 24 h / 100 °C
  • 11
  • [ 1805523-36-7 ]
  • [ 2839672-16-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dimethyl sulfoxide; acetonitrile / 10 h / 70 °C 2: triethylsilane; palladium diacetate; tricyclohexylphosphine; sodium carbonate / N,N-dimethyl-formamide / 24 h / 100 °C 3: acetic acid; 2-picoline borane complex / methanol / 16 h / 25 °C / Inert atmosphere
  • 12
  • [ 1805523-36-7 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
34.86 % With triethylamine In dimethyl sulfoxide; acetonitrile at 70℃; 1 Step 1 To a solution of methyl 2-bromo-3,4-difluoro-benzoate (1.2 g, 4.78 mmol, 1.52 eq) in MeCN (10 mL) and DMSO (3 mL) was added TEA (1.22 g, 12.02 mmol, 1.67 mL, 3.83 eq) and tert-butyl 4-[4-(4-piperidyloxy)cyclohexoxy]piperidine-1-carboxylate (1.2 g, 3.14 mmol, 1 eq) at 20°C, and the reaction mixture was stirred at 70°C for 10 hour. TLC showed there was a new spot. The residue was poured into water (10 mL). The aqueous phase was extracted with ethyl acetate (10 mL * 3). The combined organic phase was washed with brine (10 mL * 2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (0-15% of Ethyl acetate in Petroleum ether, 15% of Ethyl acetate in Petroleum ether) to give tert-butyl 4-[4-[[1-(3-bromo-2-fluoro-4-methoxycarbonyl-phenyl)-4- piperidyl]oxy]cyclohexoxy]piperidine-1-carboxylate (700 mg, 1.09 mmol, 34.86% yield, 95.84% purity) as a white solid.
34.86 % With triethylamine In dimethyl sulfoxide; acetonitrile at 70℃; 1 Step 1 To a solution of methyl 2-bromo-3,4-difluoro-benzoate (1.2 g, 4.78 mmol, 1.52 eq) in MeCN (10 mL) and DMSO (3 mL) was added TEA (1.22 g, 12.02 mmol, 1.67 mL, 3.83 eq) and tert-butyl 4-[4-(4-piperidyloxy)cyclohexoxy]piperidine-1-carboxylate (1.2 g, 3.14 mmol, 1 eq) at 20°C, and the reaction mixture was stirred at 70°C for 10 hour. TLC showed there was a new spot. The residue was poured into water (10 mL). The aqueous phase was extracted with ethyl acetate (10 mL * 3). The combined organic phase was washed with brine (10 mL * 2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (0-15% of Ethyl acetate in Petroleum ether, 15% of Ethyl acetate in Petroleum ether) to give tert-butyl 4-[4-[[1-(3-bromo-2-fluoro-4-methoxycarbonyl-phenyl)-4- piperidyl]oxy]cyclohexoxy]piperidine-1-carboxylate (700 mg, 1.09 mmol, 34.86% yield, 95.84% purity) as a white solid.
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