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[ CAS No. 865156-59-8 ] {[proInfo.proName]}

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Chemical Structure| 865156-59-8
Chemical Structure| 865156-59-8
Structure of 865156-59-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 865156-59-8 ]

CAS No. :865156-59-8 MDL No. :MFCD16610030
Formula : C6H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :RXVJMXCAYIZVKM-UHFFFAOYSA-N
M.W : 188.02 Pubchem ID :23149472
Synonyms :

Calculated chemistry of [ 865156-59-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.93
TPSA : 33.12 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) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.71
Solubility : 0.368 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 1.08 mg/ml ; 0.00577 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.69
Solubility : 0.383 mg/ml ; 0.00204 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 865156-59-8 ]

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

Application In Synthesis of [ 865156-59-8 ]

* 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.

  • Upstream synthesis route of [ 865156-59-8 ]
  • Downstream synthetic route of [ 865156-59-8 ]

[ 865156-59-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 3749-51-7 ]
  • [ 865156-59-8 ]
YieldReaction ConditionsOperation in experiment
90% With phosphorus(V) oxybromide In N,N-dimethyl-formamide at 110℃; for 1 h; 4-hydroxy-6-methylpyridin-2(1H)-one (500 mg, 4.00 mmol) was mixed with phosphoryl bromide (881 mg, 3.07 mmol) and DMF (1.8 mL) was added. The reaction mixture was heated at 110 oC. After 5 min, more DMF (1.8 mL) was added and the reaction was heated at 110 oC for 1 h. The reaction was cooled down and ice cold water was carefully added, followed by solid sodium bicarbonate until pH reached 7. The precipitate was filtered, rinced with cold water and let dry under air to give the title compound (520 mg, 2.77 mmol, 90percent).
90% With phosphorus(V) oxybromide In N,N-dimethyl-formamide at 110℃; for 1.08333 h; 4-hydroxy-6-methylpyridin-2(1H)-one (500 mg, 4.00 mmol) was mixed with phosphoryl bromide (881 mg, 3.07 mmol) and DMF (1.8 mL) was added. The reaction mixture was heated at 110 0 After 5 mm, more DMF (1.8 mL) was added and the reaction was heated at 110 00 for 1 h. The reaction was cooled down and ice cold water was carefully added, followed by solid sodium bicarbonate until pH reached 7. The precipitate was filtered, rinced with cold water and let dry under air to give the title compound (520 mg, 2.77 mmol, 90percent).
Reference: [1] Patent: WO2016/196644, 2016, A1, . Location in patent: Paragraph 574; 575
[2] Patent: WO2018/102452, 2018, A2, . Location in patent: Paragraph 558; 559
  • 2
  • [ 3749-51-7 ]
  • [ 865156-59-8 ]
Reference: [1] Patent: WO2007/131991, 2007, A1, . Location in patent: Page/Page column 86
  • 3
  • [ 67-56-1 ]
  • [ 865156-59-8 ]
  • [ 1083169-00-9 ]
YieldReaction ConditionsOperation in experiment
30% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 18 h; Diisopropyl diazocarboxylate (323 mg, 1.60 mmol) was added to a solution of 4- bromo-6-methylpyridin-2-ol (200 mg, 1.06 mmol), methanol (54 ^L, 1.3 mmol) and triphenylphosphine (419 mg, 1.60 mmol) in THF (4.6 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (5 to 10percent) to give the title compound (65 mg, 0.32 mmol, 30percent).
30% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 18 h; Diisopropyl diazocarboxylate (323 mg, 1.60 mmol) was added to a solution of 4- bromo-6-methylpyridin-2-ol (200 mg, 1.06 mmol), methanol (54 iL, 1.3 mmol) and triphenylphosphine (419 mg, 1.60 mmol) in THF (4.6 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1 N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (5 to 10percent) to give the title compound (65 mg, 0.32 mmol, 30percent).
Reference: [1] Patent: WO2016/196644, 2016, A1, . Location in patent: Paragraph 675; 676
[2] Patent: WO2018/102452, 2018, A2, . Location in patent: Paragraph 659; 660
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