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[ CAS No. 192642-85-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 192642-85-6
Chemical Structure| 192642-85-6
Chemical Structure| 192642-85-6
Structure of 192642-85-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 192642-85-6 ]

CAS No. :192642-85-6 MDL No. :MFCD09999983
Formula : C7H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ATKULCGQSLCGEK-UHFFFAOYSA-N
M.W : 216.03 Pubchem ID :46238459
Synonyms :

Calculated chemistry of [ 192642-85-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.48
TPSA : 50.19 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) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : 1.47
Log Po/w (MLOGP) : 0.82
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.69 mg/ml ; 0.00783 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 4.47 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.469 mg/ml ; 0.00217 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 192642-85-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 192642-85-6 ]

* 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 [ 192642-85-6 ]
  • Downstream synthetic route of [ 192642-85-6 ]

[ 192642-85-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1215098-80-8 ]
  • [ 192642-85-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With water; sodium hydroxide In methanol at 20℃; for 3 h;
Stage #2: With hydrogenchloride In water
Example 40 5-(Bromo-pyridin-2-yl)-acetic acidTo a solution of 2-(5-Bromo-pyridin-2-yl)-malonic acid diethyl ester (16.6 g, 52.5 mmol) in MeOH (200 mL) was added aq. NaOH (2N, 105 mL, 210 mmol). The solution was stirred at room temperature for 3 h, then concentrated in vacuo. The residue was dissolved in water and neutralized with 2N HCl to pH 3-4. Then the solid was filtered and washed with water, ether, dried to give a white solid product without further purification (9.0 g, 80percent). MS: calc'd 215 (MH+), exp 215 (MH+).
70% With sodium hydroxide In methanol; water at 20℃; for 3 h; To a solution of diethyl 2-(5-bromopyridin-2-yl)malonate 166 (2.1 g, 6.6 mmol) in MeOH (30 mL) was added 2 M NaOH aqueous solution (14 mL, 28 mmol). The resulting mixture was stirred at room temperature for 3 hours. The solution was concentrated under reduced pressure and the residue was dissolved in water (20 mL). The pH of the solution was adjusted to 3-4 by addition of 6 M HCI. The white precipitate formed was collected by filtration, washed with water and dried at 50 °C to give the title compound as a white solid (1 .0 g, 70percent). LCMS-C: RT 0.78 min; m/z 216.0 [M+H]+.
Reference: [1] Patent: US2010/69328, 2010, A1, . Location in patent: Page/Page column 36
[2] Patent: WO2016/34673, 2016, A1, . Location in patent: Page/Page column 100
[3] Patent: WO2014/53967, 2014, A1, . Location in patent: Page/Page column 160; 161
  • 2
  • [ 192642-83-4 ]
  • [ 192642-85-6 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 24, p. 8257 - 8268
[2] Patent: WO2011/45703, 2011, A2, . Location in patent: Page/Page column 34
  • 3
  • [ 2402-97-3 ]
  • [ 192642-85-6 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 24, p. 8257 - 8268
[2] Patent: WO2011/45703, 2011, A2,
  • 4
  • [ 223463-13-6 ]
  • [ 192642-85-6 ]
Reference: [1] Patent: WO2014/53967, 2014, A1,
[2] Patent: WO2016/34673, 2016, A1,
  • 5
  • [ 626-55-1 ]
  • [ 192642-85-6 ]
Reference: [1] Patent: WO2011/45703, 2011, A2,
  • 6
  • [ 67-56-1 ]
  • [ 192642-85-6 ]
  • [ 917023-06-4 ]
YieldReaction ConditionsOperation in experiment
90% at 0 - 20℃; for 3 h; Example 41 ; (5-Bromo-pyridin-2-yl)-acetic acid methyl esterTo a solution of 5-(Bromo-pyridin-2-yl)-acetic acid (9 g, 41.7 mmol) in MeOH (80 mL), SOCl2 (10 g, 83.4 mmol) was added at 0 degrees Celsius, then the mixture stirred at room temperature for 3 h. After cooling, the solution was evaporated to dryness under reduced pressure, then EtOAc was added and the mixture was washed with aq. NaHCO3, the organic layer was dried with MgSO4, and evaporated to give the compound as an oil (8.6 g, 90percent). MS: calc'd 229 (MH+), exp 229 (MH+).
Reference: [1] Patent: US2010/69328, 2010, A1, . Location in patent: Page/Page column 36
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