Structure of 850142-72-2
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 850142-72-2 |
Formula : | C5H3BrFNO |
M.W : | 191.99 |
SMILES Code : | OC1=CC=C(Br)N=C1F |
MDL No. : | MFCD09999156 |
InChI Key : | UWFUYQNHOZTXSF-UHFFFAOYSA-N |
Pubchem ID : | 29919875 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 33.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
33.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.55 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.96 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.11 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.05 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.74 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.76 |
Solubility | 0.335 mg/ml ; 0.00174 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.28 |
Solubility | 1.01 mg/ml ; 0.00524 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.58 |
Solubility | 0.5 mg/ml ; 0.00261 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 |
-6.08 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 |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
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) |
1.93 |
* 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 |
---|---|---|
74% | With potassium carbonate; In acetone;Reflux; | To a stirring solution of 6-bromo-2-fluoropyridin-3-ol (8.80 g, 45.8 mmol) in acetone (150 mL), potassium carbonate (12.67 g, 91.67 mmol) and iodomethane (5.71 mL, 91.7 mmol) were added. The resulting mixture was stirred under reflux overnight. The contents were filtered and the solvent removed in vacuo to give a residue which was purified by automated normal-phase chromatography (0-30% EtOAc/heptane) to give 6-bromo-2-fluoro-3-methoxypyridine (7.00 g, 34.0 mmol, 74% yield) as a white solid. MS (ES+) m/z 206.0 [M+H]+. XH NMR (400 MHz, CDCI3) δ ppm 7.27 - 7.34 (m, 1H), 7.20 (dd, 1H), 3.88 - 3.95 (m, 3H). |
49% | With sodium methoxide; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h; | To a stirred solution of 6-bromo-2-fluoropyridin-3-ol (4.67 g, 24.3 mmol) and sodium methoxide (1.38 g, 25.5 mmol) in N,N-dimethylformamide (50 mL) was added methyl iodide (1.59 mL, 25.5 mmol) at 0 C, and the mixture was stirred at room temperature for 12 hours. The mixture was treated with H20 and extracted with ethyl acetate. The combined organic layer was dried and evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate/ hexane (1: 5 v/v), to afford the titled compound as a yellow oil (2. 43 g, 49 %). 1H) NMR (270MHz, CDC13) 8 = 7.32-7. 26 (m, 1H), 7.22-7. 15 (m, 1H), 3.90 (s, 3H) ppm. MS (EI) ; M+=205, 207 |
With potassium carbonate; In acetone; at 60℃; for 14h;Inert atmosphere; | To a mixture of compound SI23-1 (2.00 g, 10.4 mmol, 1.00 eq) in acetone (30 mL) was added K2CO3 (2.88 g, 20.8 mmol, 2.00 eq) and CH3I (2.96 g, 20.8 mmol, 2.00 eq). The mixture was stirred at 60 C for 14 hrs. under N2 atmosphere. LC-MS (EC1719-5-P1A1) showed one peak (RT = 0.527 min) with desired MS = 205.8. The reaction mixture filtered and concentrated under reduced pressure to give a residue.Compound SI23-2 (2.10 g, crude) was obtained as a yellow solid.LCMS, EC1719-5-P1A1, RT = 0.527 min, M/Z (ESI): 205.8 (M+H)+. |
With potassium carbonate; In acetone; at 60℃; for 14h;Inert atmosphere; | To a mixture of compound SI23-1 (2.00 g, 10.4 mmol, 1.00 eq) in acetone (30 mL) was added K2CO3 (2.88 g, 20.8 mmol, 2.00 eq) and CH3I (2.96 g, 20.8 mmol, 2.00 eq). The mixture was stirred at 60 C for 14 hrs. under N2 atmosphere. LC-MS (EC1719-5-P1A1) showed one peak (RT = 0.527 min) with desired MS = 205.8. The reaction mixture filtered and concentrated under reduced pressure to give a residue.Compound SI23-2 (2.10 g, crude) was obtained as a yellow solid.LCMS, EC1719-5-P1A1, RT = 0.527 min, M/Z (ESI): 205.8 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | In DMF (N,N-dimethyl-formamide); at 0 - 25℃; for 12h; | B. 6-bromo-2-fluoro-3-methoxypyridine; To a stirred solution of 6-bromo-2-fluoropyridin-3-ol (4.67 g, 24.3 mmol) and sodium methoxide (1.38 g, 25.5 mmol) in N, N dimethylformamide (50 mL) was added methyl iodide (1.59 mL, 25.5 mmol) at 0 C, and the mixture was stirred at room temperature for 12 hours. The mixture was treated with H20 and extracted with ethyl acetate. The combined organic layer was dried and evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate/hexane (1: 5 v/v), to afford the titled compound as a yellow oil (2.43 g, 49 %). 'H NMR (270MHz, CD13) 7.32-7. 26 (m, 1H), 7.22-7. 15 (m, 1H), 3.90 (s, 3H) ppm. MS (EI) ; M+=205, 207 |
A484454 [916737-77-4]
6-Bromo-3-methoxypyridin-2-amine
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