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Structure of 57863-69-1
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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. : | 57863-69-1 |
Formula : | C8H3BrCl2O2 |
M.W : | 281.92 |
SMILES Code : | O=C(Cl)C1=CC(Br)=CC(C(Cl)=O)=C1 |
MDL No. : | MFCD28009845 |
InChI Key : | MMGMYZMTUVIVSU-UHFFFAOYSA-N |
Pubchem ID : | 15320483 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 54.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
34.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.13 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.63 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.21 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.62 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.08 |
Solubility | 0.0232 mg/ml ; 0.0000824 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.03 |
Solubility | 0.026 mg/ml ; 0.0000923 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.38 |
Solubility | 0.0119 mg/ml ; 0.0000422 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) |
Yes |
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 |
-5.44 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 |
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) |
1.72 |
* 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 |
---|---|---|
With oxalyl dichloride;N,N-dimethyl-formamide; In tetrahydrofuran; for 1h; | 5-Bromo-N,N'-dimethoxy-N,N'-dimethylisophthalamide. Oxalyl chloride (3.19 mL, 36.6 mmol) and DMF (one drop, catalyst) were added dropwise to a solution of <strong>[23351-91-9]5-bromoisophthalic acid</strong> (4.48 g, 18.3 mmol) in anhydrous THF (150 mL). After stirring for 1 hour the solvent was removed in vacuo. The crude yellow oil was dissolved in CHCl3(150 mL), N,O-dimethylhydroxylamine hydrochloride (1.96 g, 20.1 mmol) was added, and the reaction was chilled (0 C.) as the triethylamine (5.07 mL, 36.6 mmol) was added dropwise. The ice bath was removed and the reaction was allowed to stir at room temperature for 2 hours. The solvent was removed in vacuo and the residue was partitioned between saturated NH4Cl solution and CHCl3. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated to give a brown oil. This material was chromatographed on silica gel eluting with 60% EtOAc in hexanes to give 5-bromo-N,N'-dimethoxy-N,N'-dimethylisophthalamide as a white solid. 1H NMR (400 MHz, CDCl3) delta7.94(s, 1H), 7.93(s, 2H), 3.57(s, 6H), 3.38 (s, 6H). | |
With thionyl chloride; for 7h;Heating / reflux; | Placing Intermediate B in an amount of 25.0 g (102mmol) and thionyl chloride in an amount of 250 g into a flask, the resultant solution was reacted for 7 hours under refluxing. Dissolving a resultant solid into 250 milliliter of toluene, a solution prepared by dissolving t-butylamine in an amount of 37.7 g (515 mmol) into toluene was dripped into the former solution at a temperature of 5 to 18 C. The temperature of the resultant solution was elevated little by little up to the room temperature, and adding 200 milliliter of water, the solution was stirred. A deposit was separated by filtration and as a result, 35.0 g of Compound C was obtained (yield: 96 %). | |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h; | 5-Bromobenzene-l,3-dicarboxylic acid (l.OOg, 4.08mmol) was dissolved in DCM (20mL) and oxalyl chloride (876uL, 10.2mmol) and DMF (200uL) were added. The reaction mixture was stirred for 2h and concentrated in vacuo. The residue was dissolved in MeOH (20mL), stirred for 18h and partitioned between DCM (lOOmL) and sat aq Na2CC>3 (50mL). The aqueous fraction was extracted with DCM (50mL) and the combined organic fractions were dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (1.04g, 93%) as a white solid. LCMS: ES+ 272.9, 274.9 [MH]+. |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h; | 5-Bromobenzene-1,3-dicarboxylic acid (1.OOg, 4.O8mmol) was dissolved in DCM(2OmL) and oxalyl chloride (876uL, 10.2mmol) and DIVIF (200uL) were added. The reaction mixture was stirred for 2h and concentrated in vacuo. The residue was dissolved in MeOH (2OmL), stirred for 18h and partitioned between DCM (lOOmL) and sat aq Na2CO3 (5OmL). The aqueous fraction was extracted with DCM (5OmL) and the combined organic fractions were dried (Mg504) and concentrated in vacuo. The residuewas purified by column chromatography to give the title compound (1.04g, 93%) as a white solid. LCMS: ES 272.9, 274.9 [IVIHf. | |
With thionyl chloride; N,N-dimethyl-formamide;Reflux; Inert atmosphere; | A mixture of <strong>[23351-91-9]5-bromoisophthalic acid</strong> (15.0 g, 61.2 mmol) in thionyl chloride (60 mL) with 0.2 mL dimethylformamide (DMF) was heated to reflux overnight under argon. After removing the excess thionyl chloride under reduced pressure, the remaining liquid was dissolved in anhydrous CH2Cl2 (200 mL). To the solution was added N-phenyl-o-phenyldiamine (22.5 g, 122 mmol), followed by slow addition of triethylamine (22.2 mL, 159 mmol) with ice-bath cooling. The mixture was allowed to warm to RT overnight. The resulting suspension was then diluted with CH2Cl2 (200 mL), filtered and the filtrant washed with CH2Cl2 to provide Compound 6 (30.3 g, 86%) as an off-white solid: confirmed by LCMS (APCI): calculated for C32H25BrN4O2 (M+): 577; Found: 577. | |
With thionyl chloride; In N,N-dimethyl-formamide;Reflux; Inert atmosphere; | Example 1.2.6 5-Bromo-N1,N3-bis(2-(phenylamino)phenyl)isophthalamide (Compound 6) A mixture of <strong>[23351-91-9]5-bromoisophthalic acid</strong> (15 g, 61.2 mmol) in thionyl chloride (60 mL) with 0.2 mL DMF was heated to reflux for overnight under argon. After removal of the excess thionyl chloride under reduced pressure, the remaining liquid was dissolved in anhydrous dichloromethane (200 mL). To the solution, N-phenyl-o-phenyldiamine (22.5 g, 122 mmol) was added, then triethylamine (22.2 mL, 160 mL) was added slowly with ice-bath cooling. The mixture was stirred overnight with slowly warming up the ice-bath to room temperature. The resulting suspension was diluted with dichloromethane (200 mL), filtered and washed with dichloromethane to give an off-white solid (30.3 g, yield: 86%). Confirmed by LCMS (APCI): calcd for C32H26BrN4O2 (M+H): 577. Found: 577. |
Tags: 57863-69-1 synthesis path| 57863-69-1 SDS| 57863-69-1 COA| 57863-69-1 purity| 57863-69-1 application| 57863-69-1 NMR| 57863-69-1 COA| 57863-69-1 structure
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
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Code | Phrase |
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H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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