Alternatived Products of [ 566203-88-1 ]
Product Details of [ 566203-88-1 ]
CAS No. : 566203-88-1
MDL No. : MFCD31382158
Formula :
C11 H9 Cl2 N3 O3 S
Boiling Point :
-
Linear Structure Formula : -
InChI Key : FLSMVCMSUNISFK-UHFFFAOYSA-N
M.W :
334.18
Pubchem ID : 10308720
Synonyms :
Calculated chemistry of [ 566203-88-1 ]
Physicochemical Properties
Num. heavy atoms :
20
Num. arom. heavy atoms :
12
Fraction Csp3 :
0.09
Num. rotatable bonds :
4
Num. H-bond acceptors :
5.0
Num. H-bond donors :
1.0
Molar Refractivity :
75.66
TPSA :
89.56 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
No
P-gp substrate :
No
CYP1A2 inhibitor :
Yes
CYP2C19 inhibitor :
Yes
CYP2C9 inhibitor :
Yes
CYP2D6 inhibitor :
No
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-6.46 cm/s
Lipophilicity
Log Po/w (iLOGP) :
1.89
Log Po/w (XLOGP3) :
2.64
Log Po/w (WLOGP) :
3.48
Log Po/w (MLOGP) :
0.78
Log Po/w (SILICOS-IT) :
1.77
Consensus Log Po/w :
2.11
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-3.76
Solubility :
0.0587 mg/ml ; 0.000176 mol/l
Class :
Soluble
Log S (Ali) :
-4.17
Solubility :
0.0225 mg/ml ; 0.0000674 mol/l
Class :
Moderately soluble
Log S (SILICOS-IT) :
-5.48
Solubility :
0.00111 mg/ml ; 0.00000333 mol/l
Class :
Moderately soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
0.0
Synthetic accessibility :
3.06
Safety of [ 566203-88-1 ]
Application In Synthesis of [ 566203-88-1 ]
* 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 [ 566203-88-1 ]
1
[ 566203-88-1 ]
[ 942137-52-2 ]
Yield Reaction Conditions Operation in experiment
77%
With nitric acid In acetic acid at 20℃; for 1h; Heating; regioselective reaction;
With nitric acid In acetic acid at 20 - 75℃; for 1h;
2.a
Fuming nitric acid (1.26g) was added dropwise to a stirred suspension of 2,3-dichloro- N-(3-methoxypyrazin-2-yl)-benzenesulfonamide (WO2003059893, example 30) (4.5g) in acetic acid (45ml) at room temperature. The reaction was carefully heated to 750C. After Ih, the reaction mixture was allowed to cool and the white crytalline product collected by filtration. Yield 3.94g. IH NMR (D6-DMSO) δ 8.53 (IH, s), 8.16 (IH, d), 7.95 (IH5 d), 7.61 (IH, t) 4.02 (3H, s).
Reference:
[1]Kindon, Nicholas; Andrews, Glen; Baxter, Andrew; Cheshire, David; Hemsley, Paul; Johnson, Timothy; Liu, Yu-Zhen; McGinnity, Dermot; McHale, Mark; Mete, Antonio; Reuberson, James; Roberts, Bryan; Steele, John; Teobald, Barry; Unitt, John; Vaughan, Deborah; Walters, Iain; Stocks, Michael J.
[ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 981 - 986]
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2007/69978, 2007, A1
Location in patent: Page/Page column 28
2
[ 566203-88-1 ]
[ 942137-41-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: nitric acid / acetic acid / 1 h / 20 °C / Heating
2: hydrogen; 5%-palladium/activated carbon; acetic acid / 16 h / 60 °C / 750.08 Torr
3: sodium nitrite; tetrafluoroboric acid / water; acetonitrile / 1 h / 0 - 5 °C
Reference:
[1]Kindon, Nicholas; Andrews, Glen; Baxter, Andrew; Cheshire, David; Hemsley, Paul; Johnson, Timothy; Liu, Yu-Zhen; McGinnity, Dermot; McHale, Mark; Mete, Antonio; Reuberson, James; Roberts, Bryan; Steele, John; Teobald, Barry; Unitt, John; Vaughan, Deborah; Walters, Iain; Stocks, Michael J.
[ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 981 - 986]
3
[ 566203-88-1 ]
[ 942137-53-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: nitric acid / acetic acid / 1 h / 20 °C / Heating
2: hydrogen; 5%-palladium/activated carbon; acetic acid / 16 h / 60 °C / 750.08 Torr
Reference:
[1]Kindon, Nicholas; Andrews, Glen; Baxter, Andrew; Cheshire, David; Hemsley, Paul; Johnson, Timothy; Liu, Yu-Zhen; McGinnity, Dermot; McHale, Mark; Mete, Antonio; Reuberson, James; Roberts, Bryan; Steele, John; Teobald, Barry; Unitt, John; Vaughan, Deborah; Walters, Iain; Stocks, Michael J.
[ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 981 - 986]
4
[ 5900-13-0 ]
2,3-dichloro-N-(3-methoxypyrazin-2-yl)benzenesulfonamide
[ No CAS ]
5
[ 4774-10-1 ]
[ 82417-45-6 ]
2,3-dichloro-N-(3-methoxypyrazin-2-yl)benzenesulfonamide
[ No CAS ]
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