Structure of 221037-98-5
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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. : | 221037-98-5 |
Formula : | C6H6BIO2 |
M.W : | 247.83 |
SMILES Code : | IC1=CC=CC(=C1)B(O)O |
MDL No. : | MFCD01319015 |
InChI Key : | REEUXWXIMNEIIN-UHFFFAOYSA-N |
Pubchem ID : | 2734362 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 48.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.48 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.58 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.69 |
Solubility | 0.51 mg/ml ; 0.00206 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.94 |
Solubility | 2.87 mg/ml ; 0.0116 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.24 |
Solubility | 1.41 mg/ml ; 0.0057 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 |
No |
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 |
-6.76 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 |
2.0 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) |
2.68 |
* 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 |
---|---|---|
In toluene;Reflux; | Into iodobenzeneboronic acid (186 g, 0.75 mol) and 700 (2 mL) were added to 1 L of a three-necked flask equipped with a reflux water separatorMl of toluene, heated to reflux water, when the system separated about 17.5-14.0 grams of water, and the system no longer continue to separate water,Stop the reaction. After cooling, the heptane is distilled to a non-flowing liquid to give crude tri-iodobenzene triol, which contains about 5-8percentbenzene. Can be directly into the next step reaction.Synthesis of aldehyde aldehyde phenylboronic acid:Under nitrogen protection, the above-obtained iodobenzeneboronic acid trimer was added to 500 ml of anhydrous tetrahydrofuranAfter the addition, the mixture was transferred to a 2 L three-necked flask and dimethylformamide (65.7 g, 0.90 mol) was added. Then cool the system to -75 ° C to -80 ° C, 609 ml (0.98 mol) of 1.6 M n-butyllithium hexane solution was slowly added dropwise, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; copper diacetate; In dichloromethane;Molecular sieve; under an oxygen balloon; | To a solution of 3-iodo-phenylboronic acid (991 mg, 4 mmol) and 1-benzofuran-6-ol (269 mg, 2 mmol) in dichloromethane (8 mL) was added copper acetate (363 mg, 2 mmol), pyridine (0.8 mL, 10 mmol) and 4A molecular sieves (300 mg). The reaction mixture was degassed and stirred under an oxygen balloon overnight. It was then filtered and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (0-10percent) in hexanes, to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; for 0.25h;Heating / reflux; Molecular sieves; | A mixture of <strong>[221037-98-5]3-iodophenylboronic acid</strong> (15 g) and 1, 3-diphenyl-1, 3-propanediol (15 g) in tetrahydrofuran (150 ML) was heated to reflux for 15 min in the presence of molecular sieves. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was crystallised from heptane-ethyl acetate (5: 1) to give the title compound (25.3 g) LCMS RT = 3.03 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; copper diacetate; In dichloromethane; at 20℃;4A molecular sieves; | To a stirred solution of Intemediate 1 (1.9 g, 8.5 mmol) in dichloromethane (20 mL) was added 3- iodophenylboronic acid (3.0 g, 12.1 mmol), copper(II) acetate (2.0 g, 11 mmol), pyridine (3.2 mL, 40 mmol), and 4A molecular sieves (~2.5 g). The resulting mixture was stirred under an oxygen balloon at room temperature overnight. The reaction mixuture was filtered, washed with dichloromethane, and concentrated. The greenish crude product was purified on a silica gel column, eluting with ethyl acetate (20-50percent) in hexanes to afford the desired product. LCMS for C 19Hl 9103: calc. 422, observed 423 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Example 1.52; Preparation of the intermediate (4-bromo-2-methyl-2H-pyrazoI-3-yI)-(3-iodo-phenyl)- amine.A 500-mL round bottom flask was charged with toluene (50 mL), copper(IT) acetate (0.62 g, 3.41 mmol), myristic acid (1.17 g, 5.11 mmol), and roe-iodophenylboronic acid (5.00 g, 20.18 mmol) then stirred at room temperature for five minutes. While mixing, 2,6-lutidine (1.99 mL, 17.04 mmol) was added and allowed to stir for an additional 10 minutes. 3-amino-4-bromo- 2-methyl pyrazole (3.00 g, 17.04 mmol) was added then reaction mixture stirred at room temperature overnight. Ethyl acetate was added, washed with ammonium hydroxide, water and brine. The ammonium salt formed, suspended in the organic layer, was removed by filtration. The filtrate was washed with water twice, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to yield a crude yellow oil, that was purified by column EPO <DP n="87"/>chromatography on silica gel (Biotage, hexanes/ethyl acetate, gradient elution) to afford (4- bromo-2-methyl-2H-pyrazol-3-yl)-(3-iodo-phenyl)-amine as a yellow solid. Yield: 3.25 g (51 percent). LCMS m/z (percent) = 378 (M+Eta 79Br, 100), 380 (M+Eta 81Br, 88). 1H NMR (400MHz, DMSO- d6): delta 8.15 (s, IH), 7.61 (s, IH), 7.09 (d, J=8.0 Hz, IH), 6.96 (dd, J=8.0, 8.0 Hz, IH), 6.90 (dd, J=I.8, 1.8 Hz, IH), 6.52 (dd, J=8.0, 1.6 Hz, IH), 3.63 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | General procedure: NaN3 (1.2 equiv), CuSO4 (0.1 equiv), and boronic acids (1.2 equiv) in methanol (10 mL) were allowed to react for 1?4 h, followed by addition of water (10 mL), sodium ascorbate (0.5 equiv), and propargylated alpha-desmotroposantonin (1.0 equiv) [34]. The contents were stirred vigorously at room temperature for 2?8 h (as monitored by TLC analysis). After completion of the reaction, the contents diluted with water and extracted with ethyl acetate (3 times). The combined ethyl acetate extract was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure on a rota vapour. The crude product obtained thus subjected was put to column chromatography (silica gel) with EtOAc:Hexane (15:85) mixture as eluent to afford the desired pure products in >97percent yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With [bis(acetoxy)iodo]benzene; triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; at 20℃; for 3h; | General procedure: To a mixture of benzoic acid (1 mmol), carbonyldiimidazole (1mmol), triethylamine, (5 mmol) and boronic acid (1 mmol) in dichlorormethane (5mL) were charged to PhI(OAc)2 (0.38g, 1.2 mmol). The reaction mixture was stirred at room temperature for 3h. After complete conversion, as indicated by TLC (9:1 Hexane:EtOAc), the reaction mixture was evaporated under reduced pressure and theresidue was purified by flash column chromatography on silica gel (2percent ethylacetate inpetroleum ether) to give the product. |
A129133 [374790-98-4]
2-Fluoro-4-iodophenylboronic acid
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A129133 [374790-98-4]
2-Fluoro-4-iodophenylboronic acid
Similarity: 0.72