Structure of 1296950-96-3
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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. : | 1296950-96-3 |
Formula : | C10H7BrN2O |
M.W : | 251.08 |
SMILES Code : | O=C(C1=CC2=CC(Br)=CC=C2N=C1)N |
MDL No. : | MFCD18909572 |
InChI Key : | DKTGQKFNZHZSQH-UHFFFAOYSA-N |
Pubchem ID : | 71720990 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 57.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.98 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.75 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.1 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.86 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.96 |
Solubility | 0.274 mg/ml ; 0.00109 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.54 |
Solubility | 0.72 mg/ml ; 0.00287 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.15 |
Solubility | 0.0179 mg/ml ; 0.0000713 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-6.59 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 |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.32 |
* 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 |
---|---|---|
92% | Example 22 3-(4-Cyclobutyl-thiazol-2-yl)-quinoline-6-carboxylic acid Step 1 To a suspension of 6-bromoquinoline-3-carboxylic acid (0.50 g, 1.98 mmol) in dichloromethane (10 ml) was added oxalyl chloride (327 mg, 0.22 ml, 2.58 mmol) followed by DMF (3 drops). Gentle gas evolution was observed. The reaction mixture was stirred at room temperature for 2 h then concentrated to a white solid. The residue was suspended in diethyl ether (10 ml) and 28% ammonium hydroxide (2.0 ml, 16.0 mmol) was added. The mixture was stirred vigorously at room temperature for 2 h then filtered, rinsing with water and diethyl ether. Dried to by air then under high vacuum to afford 457 mg (92%) of 6-bromo-quinoline-3-carboxylic acid amide as a beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With Lawessons reagent; In tetrahydrofuran; at 60℃; | Step 2 To a solution of 6-bromo-quinoline-3-carboxylic acid amide (450 mg, 1.79 mmol) in THF (12 ml) was added Lawesson's reagent (1.09 g, 2.69 mmol). The reaction mixture was heated at 60C overnight then cooled to room temperature and concentrated. The residue was triturated with toluene/dichloromethane/MeOH. The resultant precipitate was collected via filtration, rinsing with toluene and dried under high vacuum to provide 340 mg (71%) of 6-bromo-quinoline-3- carbothioic acid amide as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta: 10.22 (br. s., 1H), 9.90 (br. s., 1H), 9.31 (d, J = 2.3 Hz, 1H), 8.70 (d, J = 2.3 Hz, 1H), 8.38 (d, J = 1.9 Hz, 1H), 7.91 - 8.03 (m, 2H). |
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