Structure of 2243-47-2
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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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CAS No. : | 2243-47-2 |
Formula : | C12H11N |
M.W : | 169.22 |
SMILES Code : | NC1=CC(C2=CC=CC=C2)=CC=C1 |
MDL No. : | MFCD00047846 |
InChI Key : | MUNOBADFTHUUFG-UHFFFAOYSA-N |
Pubchem ID : | 16717 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 56.28 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.87 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.9 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.94 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.07 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.85 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.73 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.33 |
Solubility | 0.0786 mg/ml ; 0.000464 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.11 |
Solubility | 0.132 mg/ml ; 0.000782 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.55 |
Solubility | 0.00479 mg/ml ; 0.0000283 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) |
Yes |
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 |
-5.27 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 |
2.0 |
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) |
1.24 |
* 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 hydrogen;palladium 10% on activated carbon; In ethanol; for 3h; | Palladium on carbon (10%, 0.70 g, 0.658 mmol) was added to a Parr hydrogenator bottle. The bottle was purged with nitrogen. Next, 3- nitro-l,l'-biphenyl (10 g, 50.2 mmol) and 190 mL ethanol were added to the bottle. The material was hydrogenated on a Parr hydrogenator. After 3 h, the reaction mixture was filtered through Celite and the Celite washed with dichloromethane. The filtrate was evaporated, obtained a brown oil, 8.69 g, assume quantitative yield (8.49 g). |
99.7% | Another batch of reaction was effected on the same scale except that 254 g (1.28 mol) of <strong>[2113-58-8]m-nitrobiphenyl</strong> was used, obtaining 215 g of m-aminobiphenyl (yield 99.7%). | |
94% | palladium; In ethyl acetate; | a) 3-phenylaniline To a stirring solution of <strong>[2113-58-8]3-nitrobiphenyl</strong> (1.2 g, 6.0 mmol) in ethyl acetate (25 mL) was added 10% Palladium on carbon (500 mg, 40% w/w). After stirring under a balloon of hydrogen for 24 h, the mixture was filtered through Celite and concentrated to yield the title compound as a white solid (0.956 g, 94%). MS (ESI): 170.0 (M+H)+. |
16 g (95%) | palladium-carbon; In methanol; chloroform; | Example 1 Synthesis of 3-aminobiphenyl (1): The following compound is prepared: STR26 A mixture of <strong>[2113-58-8]3-nitrobiphenyl</strong> (20 g, 100 mmol) and 10% Pd/C (2 g) in MeOH/CHCl3 (300 mL, 1:1) is hydrogenated at 40 psi for 4 hours. The mixture is suction filtered through a layer of diatomaceous earth and washed with MeOH. The filtrate is evaporated to dryness and the solid is further dried under vacuum to give 16 g (95%) of 3-aminobiphenyl. |
(a) In a manner similar to that of Example 7(b), <strong>[2113-58-8]3-nitrobiphenyl</strong> (2.48 g) gives 1.77 g of 3-aminobiphenyl, mp 27.5-28.5 C. | ||
With hydrogen;palladium 10% on activated carbon; In methanol; | Example 11; 3-aminobiphenyl: <strong>[2113-58-8]3-nitrobiphenyl</strong> (500 mg, 2.5 mmol) and 10% palladium on carbon (267 mg, 2.5 mmol) were dissolved in methanol (1 mL) and purged with nitrogen and placed under an atmosphere of hydrogen overnight. The reaction mixture was filtered and evaporated to yield 326 mg of the desired amine, which was used directly in Example 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.9% | In ethanol; | Example 1 A 2-l atmospheric hydrogenation reactor was charged with 250 g (1.26 mol) of <strong>[2113-58-8]m-nitrobiphenyl</strong>, 12.5 g of 5% Pd-Cl, and 1250 ml of ethanol. A theoretical amount of hydrogen gas was absorbed at room temperature. The catalyst was removed by filtration and the filtrate was distilled of the solvent, obtaining 212 g of m-aminobiphenyl (yield 99.9%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35%; 25% | With triethylsilane; palladium dichloride; In tetrahydrofuran; for 96h;Inert atmosphere; Reflux; | General procedure: To a solution of aryl alkyl sulfide (0.23 mmol, 1.0 equiv) and PdCl2 (0.007 mmol, 3 mol %, 1.2 mg) in 2 mL of THF was added triethylsilane (amount indicated in Table 3) under argon atmosphere (color of the reaction mixture turned to black). The resulting mixture was stirred at room temperature (or at the indicated temperature in Table 3). After completion of the reaction, to the reaction mixture was added 4 mL of H2O (gas evolves). The aqueous layer was extracted with CH2Cl2 (4 mL × 2), and the combined organic layer was dried over Na2SO4 and evaporated. The residue was purified by silica gel column chromatography using hexane/ethyl acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1 : tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (69 mg, 0.287 mol) was added to a cooled solution of the <strong>[3177-24-0]2,4-dichloropyrimidine-5-carbonitrile</strong> (50 mg, 0.287 mmol) and Hunig's base (50 uL, 0.287 mmol) in CH2CI2 (1.5 mL) and the reaction mixture was stirred for 3 hours at 0 °C. The solvent was removed under reduced pressure, then the mixture was diluted with CH3CN (2 mL) and the biphenyl-3 -amine (97 mg, 0.575 mol) was added. The mixture was then heated to 80 °C overnight. Upon cooling, the reaction mixture was diluted with ethyl acetate, washed with 0 and then brine and the organic extracts were dried ( a2S04), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) provided a mixture of the two possible isomers which was separated by the reverse phase chromatography to afford tert-butyl 8-[2-(biphenyl-3- ylamino)-5-cyanopyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-2-carboxylate. MS ESI calcd. for C3oH35 602 [M + H]+ 511 , found 51 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23.2% | To a 2-5 mL Biotage microwave vial with a stir bar were added 3-aminobiphenyl (370.5 mg, 2.189 mmol), 2-chloro-4- iodonicotinonitrile (578 mg, 2.186 mmol), Pd(OAc)2(9.6 mg, 0.043 mmol), DPEPhos (36.1 mg, 0.0671 mmol), and CS2CO3(988 mg, 3.03 mmol). The vial was sealed and treated with dioxane (4.35 mL), evacuated/flushed with argon 4X, and stirred at 150 C under argon for 30. The reaction was then cooled to room temperature, treated with tert-butyl (3R)-3-[(2- sulfanylacetyl)amino]piperidine-l -carboxylate (Intermediate 22) in dioxane (4.05 mL, 0.65 M, 2.63 mmol) via syringe, evacuated/flushed with argon 4X, and stirred at 150 C for 15 min. The reaction was then cooled to room temperature, treated with solid CDI (1.409 g, 8.689 mmol) in one portion under air, resealed and evacuated/flushed with argon 4X, and stirred at 150 C for 15 min. The reaction was diluted with EtOAc (10 mL), and washed with 0.5 M citric acid/brine (2 x 8 mL) and 2 M K2CO3(1 x 5 mL), dried over anhydrous Na2SC>4, filtered, and concentrated to dryness. The reaction mixture was purified by flash column chromatography to give the title compound as a beige foam (289 mg, 23.2% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23.2% | To a 2-5 mL Biotage microwave vial with a stir bar were added 3-aminobiphenyl (370.5 mg, 2.189 mmol) , <strong>[1171919-75-7]2-chloro-4-iodonicotinonitrile</strong> (578 mg, 2.186 mmol) , Pd (OAc)2(9.6 mg, 0.043 mmol) , DPEPhos (36.1 mg, 0.0671 mmol) , and Cs2CO3(988 mg, 3.03 mmol) . The vial was sealed and treated with dioxane (4.35 mL) , evacuated/flushed with argon 4X, and stirred at 150 under argon for 30. The reaction was then cooled to room temperature, treated with tert-butyl (3R) -3- [ (2-sulfanylacetyl) amino] piperidine-1-carboxylate (Intermediate 22) in dioxane (4.05 mL, 0.65 M, 2.63 mmol) via syringe, evacuated/flushed with argon 4X, and stirred at 150 for 15 min. The reaction was then cooled to room temperature, treated with solid CDI (1.409 g, 8.689 mmol) in one portion under air, resealed and evacuated/flushed with argon 4X, and stirred at 150 for 15 min. The reaction was diluted with EtOAc (10 mL) , and washed with 0.5 M citric acid/brine (2 x 8 mL) and 2 M K2CO3(1 x 5 mL) , dried over anhydrous Na2SO4, filtered, and concentrated to dryness. The reaction mixture was purified by flash column chromatography to give the title compound as a beige foam (289 mg, 23.2yield) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.6% | In ethanol; for 24h;Reflux; Sealed tube; | General procedure: To a Radley reaction carousel tube, add 1 equivalent 1, 1.1 equivalents of the amine, a stir bar, and 5 mL 95% ethanol. Reflux while stirring for 24 hours. After cooling to room temperature the resulting precipitate was collected by vacuum filtration, washing with 10 mL deionized water and 5 mL chloroform. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Under nitrogen protection, 5-((3r, 5r, 7r) -adamantane-1-yl)-[1,1'-biphenyl] -2-yltrifluoromethanesulfonate 82.287mmol 82.287mmol of 3-aminobiphenyl, 720mL of toluene, 246.86mmol of sodium tert-butoxide, stir and heat to 70 C, slowly add Pd2dba3 0.82287mmol, 1.6457mmol of s-PHOS, after the addition, continue to warm to 105 C and reflux After 6 hours of reaction, the temperature was lowered to 70 C., <strong>[26608-06-0]3-bromodibenzofuran</strong> was added to 80.641 mmol, and the temperature was further increased to 105 C. and refluxed for 4 h. After the reaction was completed, the temperature was lowered, and the organic phase was extracted with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%. Compound 18 was dried. Yield: 53%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Under nitrogen protection, 4-bromo-4'-adamantyl biphenyl 82.797mmol, 3-aminobiphenyl 82.797mmol, toluene 608mL, sodium tert-butoxide 248.391mmol were added to the reaction flask, stirred, and heated to 70 C Slowly add Pd2dba30.82797mmol and s-PHOS 1.6560mmol. After the addition, continue to warm to 105 C and reflux for 2h, then lower the temperature to 70 C, add <strong>[26608-06-0]3-bromodibenzofuran</strong> 81.141mmol, continue to raise to 105 C and reflux After 8 hours of reaction, the reaction was completed, the temperature was lowered, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%. Dried compound 17. Yield: 65%. |
Tags: 2243-47-2 synthesis path| 2243-47-2 SDS| 2243-47-2 COA| 2243-47-2 purity| 2243-47-2 application| 2243-47-2 NMR| 2243-47-2 COA| 2243-47-2 structure
A121876 [2113-55-5]
[1,1'-Biphenyl]-3-amine hydrochloride
Similarity: 0.97
A151591 [118727-34-7]
1,3,5-Tris(4-aminophenyl)benzene
Similarity: 0.96
A121876 [2113-55-5]
[1,1'-Biphenyl]-3-amine hydrochloride
Similarity: 0.97
A151591 [118727-34-7]
1,3,5-Tris(4-aminophenyl)benzene
Similarity: 0.96
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H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
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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