Structure of 929000-66-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 929000-66-8 |
Formula : | C6H3BrClNO2 |
M.W : | 236.45 |
SMILES Code : | O=C(C1=NC(Cl)=CC=C1Br)O |
MDL No. : | MFCD09258777 |
InChI Key : | RDZPMWLHALUNCD-UHFFFAOYSA-N |
Pubchem ID : | 26966732 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.12 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.39 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.35 |
Solubility | 1.06 mg/ml ; 0.00447 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.77 |
Solubility | 4.04 mg/ml ; 0.0171 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.87 |
Solubility | 0.316 mg/ml ; 0.00134 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.95 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.67 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridine; p-toluenesulfonyl chloride; at 0 - 12℃; for 12.0h; | Tosyl chloride (7.7 g, 40.4 mmol) was added to a solution of 2-chloro-5- bromo picolinic acid (4 g, 17 mmol) and pyridine (9.2 mL, 114 mmol) in 33 mL of t-BuOH at 00C. The reaction was then stirred at room temperature for 12 hours. NaHCO3Sat was then added and the mixture was extracted with ethyl acetate (3 times). The combined organic phases were washed with brine and dried over Na2SO4. Concentration afforded the desired compound 12 IA (quantitative). It was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) £7.85 (d, IH), 7.26 (d, IH), 1.63 (s, 9H). |
Tosyl chloride (7.7 g, 40.4 mmol) was added to a solution of 2-chloro-5- bromo picolinic acid (4 g, 17 mmol) and pyridine (9.2 mL, 114 mmol) in 33 mL of t-BuOH at 00C. The reaction was then stirred at room temperature for 12 hours. NaHCO3 (Sat.) was then added and the mixture was extracted with ethyl acetate (3 times). The combined organic phases were washed with brine and dried over Na2SO4. Evaporation of the organic solvent afforded the desired compound 94A, which is used in the next step without further purification: 1H NMR (300 MHz, DMSO-d6) delta ppm 8.27 (1 H, d), 7.63 (1 H, d), 1.57 (9 H, s). | ||
With pyridine; p-toluenesulfonyl chloride; In tert-butyl alcohol; at 0 - 20℃; for 12.0h; | Example 1D tert-butyl 3-bromo-6-chloropicolinate Tosyl chloride (7.7 g) was added to a solution of 2-chloro-5-bromo picolinic acid (4 g) and pyridine (9.2 mL) in t-butanol (33 mL) at 0 C. The reaction was then stirred at room temperature for 12 hours. NaHCO3 (aqueous, saturated) was then added and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with brine and dried over Na2SO4. Filtration and evaporation of the organic solvent provided the title compound which was used in the next step without further purification. |
With pyridine; p-toluenesulfonyl chloride; In tert-butyl alcohol; at 0 - 20℃; for 12.0h; | Example 1C tert-butyl 3-bromo-6-chloropicolinate Tosyl chloride (7.7 g) was added to a solution of 2-chloro-5-bromo picolinic acid (4 g) and pyridine (9.2 mL) in t-butanol (33 mL) at 0 C. The reaction was then stirred at room temperature for 12 hours. NaHCO3 (aqueous, saturated) was then added and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with brine and dried over Na2SO4. Filration and evaporation of the organic solvent provided the title compound which was used in the next step without further purification. | |
With pyridine; p-toluenesulfonyl chloride; at 0 - 20℃; for 12.0h; | To a solution of 2-chloro-5-bromo picolinic acid (4 g) and pyridine (9.2 mL) in i-butanol (33 mL) at 0 C was added >-toluenesulfonyl chloride (7.7 g). The resulting mixture was stirred at room temperature for 12 hours. Saturated aqueous NaHC03 solution was added, and the resulting mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to provide the title compound. |
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