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[ CAS No. 496062-16-9 ] {[proInfo.proName]}

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Chemical Structure| 496062-16-9
Chemical Structure| 496062-16-9
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Product Details of [ 496062-16-9 ]

CAS No. :496062-16-9 MDL No. :MFCD09038181
Formula : C6H8BrNOS Boiling Point : -
Linear Structure Formula :- InChI Key :FHZBITCNTMZGLI-UHFFFAOYSA-N
M.W : 222.10 Pubchem ID :21942793
Synonyms :

Calculated chemistry of [ 496062-16-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.71
TPSA : 61.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 1.99
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 3.31
Consensus Log Po/w : 1.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.71
Solubility : 0.434 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.277 mg/ml ; 0.00125 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.372 mg/ml ; 0.00167 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 496062-16-9 ]

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 [ 496062-16-9 ]

* 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 [ 496062-16-9 ]
  • Downstream synthetic route of [ 496062-16-9 ]

[ 496062-16-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 496062-15-8 ]
  • [ 496062-16-9 ]
YieldReaction ConditionsOperation in experiment
74% With hydrogenchloride; diisobutylaluminium hydride In dichloromethane; toluene Example 173
Preparation of 2-(2-bromo-5-methyl-1,3-thiazol-4-yl)ethanol
To a solution of ester prepared in Example 172 (3.80 g, 15.2 mmol) in CH2Cl2 (100 mL) was added DIBAL-H (33.4 mL, 33.4 mmol of a 1.0 M solution in toluene) at -78° C.
After 15 minutes, the solution was warmed to 0° C. and stirred for an additional 90 minutes.
An aqueous solution of 2 N HCl (50 mL) was then added dropwise to quench the excess DIBAL-H.
The solvent layers were separated and the aqueous layer extracted with CH2Cl2 (2*200 mL).
The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure.
The residue was purified by silica gel flash chromatography (5:2 hexanes/EtOAc) to yield the product (2.5 g, 74percent) as a yellowish oil that solidifies upon standing. (C6H8BrNOS) LC-MS, RT 1.38 min., M+H 221.0; 1H NMR (CDCl3): δ 2.31 (s, 3H), 2.82 (t, 2H), 2.90-3.00 (broad s, 1H), 3.89 (t, 2H).
74% With diisobutylaluminium hydride In dichloromethane; toluene at -78 - 0℃; for 1.75 h; To a solution of ester prepared in Example 172 (3.80 g, 15.2 mmol) in CH2Cl2 (100 mL) was added DIBAL-H (33.4 mL, 33.4 mmol of a 1.0 M solution in toluene) at -78° C.
After 15 minutes, the solution was warmed to 0° C. and stirred for an additional 90 minutes.
An aqueous solution of 2 N HCl (50 mL) was then added dropwise to quench the excess DIBAL-H.
The solvent layers were separated and the aqueous layer extracted with CH2Cl2 (2*200 mL).
The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure.
The residue was purified by silica gel flash chromatography (5:2 hexanes/EtOAc) to yield the product (2.5 g, 74percent) as a yellowish oil that solidifies upon standing. (C6H8BrNOS) LC-MS, RT 1.38 min., M+H 221.0; 1H NMR (CDCl3): δ 2.31 (s, 3H), 2.82 (t, 2H), 2.90-3.00 (broad s, 1H), 3.89 (t, 2H).
74% With hydrogenchloride; diisobutylaluminium hydride In dichloromethane; toluene at -78 - 0℃; for 1.75 h; To a solution of ester prepared in Example 172 (3.80 g, 15.2 mmol) in CH2Cl2 (100 mL) was added DIBAL-H (33.4 mL, 33.4 mmol of a 1.0 M solution in toluene) at -78° C.
After 15 minutes, the solution was warmed to 0° C. and stirred for an additional 90 minutes.
An aqueous solution of 2 N HCl (50 mL) was then added dropwise to quench the excess DIBAL-H.
The solvent layers were separated and the aqueous layer extracted with CH2Cl2 (2*200 mL).
The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure.
The residue was purified by silica gel flash chromatography (5:2 hexanes/EtOAc) to yield the product (2.5 g, 74percent) as a yellowish oil that solidifies upon standing. (C6H8BrNOS) LC-MS, RT 1.38 min., M+H 221.0; 1H NMR (CDCl3): δ 2.31 (s, 3H), 2.82 (t, 2H), 2.90-3.00 (broad s, 1H), 3.89 (t, 2H).
Reference: [1] Patent: US2003/216391, 2003, A1,
[2] Patent: US2018/153859, 2018, A1, . Location in patent: Paragraph 0552; 0553
[3] Patent: US2018/153860, 2018, A1, . Location in patent: Paragraph 0554; 0555
  • 2
  • [ 30414-53-0 ]
  • [ 496062-16-9 ]
Reference: [1] Patent: US2018/153859, 2018, A1,
[2] Patent: US2018/153860, 2018, A1,
  • 3
  • [ 105983-77-5 ]
  • [ 496062-16-9 ]
Reference: [1] Patent: US2018/153859, 2018, A1,
[2] Patent: US2018/153860, 2018, A1,
  • 4
  • [ 259654-73-4 ]
  • [ 496062-16-9 ]
Reference: [1] Patent: US2018/153859, 2018, A1,
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