Structure of 501-65-5
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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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Deem, Madeleine C. ; Hein, Jason E. ;
Abstract: Online HPLC reaction progress monitoring provides detailed data-rich profiles; however, extracting kinetic information requires UV-visible response factors to determine concentrations from peak areas. If the reaction's overall mass balance is known and some anal. trend for all relevant species can be recorded, it is possible to estimate the absolute response factors of all species using a system of linear equations. We delineate a method using the Microsoft Solver plug-in to convert time course profiles to reagent concentrations without anal. standards
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Purchased from AmBeed: 207739-72-8 ; 128055-74-3 ; 101-70-2 ; 28320-32-3 ; 501-65-5 ; 103-30-0 ; 1754-62-7 ; 17619-97-5
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CAS No. : | 501-65-5 |
Formula : | C14H10 |
M.W : | 178.23 |
SMILES Code : | C1(C#CC2=CC=CC=C2)=CC=CC=C1 |
MDL No. : | MFCD00004786 |
InChI Key : | JRXXLCKWQFKACW-UHFFFAOYSA-N |
Pubchem ID : | 10390 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 58.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.85 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.78 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.17 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.24 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.95 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.59 |
Solubility | 0.00457 mg/ml ; 0.0000257 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.51 |
Solubility | 0.00549 mg/ml ; 0.0000308 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.99 |
Solubility | 0.00181 mg/ml ; 0.0000101 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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 |
-3.99 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.25 |
* 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 |
---|---|---|
Preparation of Cyclopalladated Complex I' Into a mixture of 1d (1.25g, 9.28 mmol) and Pd(OAc) (1.0g, 4.46 mmol) was added toluene (15 mL), and the solution was refluxed under a slow stream of nitrogen for 0.5 h. The precipitate from the solution was quickly filtered and washed with fresh solvent to give greenish yellow I'. Then the filtrate was again refluxed for 1.5 h, and the deposited I' was collected. The total yield of I' was 1.21g, 91 percent based on palladium. The decomposed point is 205-208 oC. Spectral data was consistent with the literature that was reported previously.1; To a suspension of I'(0.08 mmol, 49.6 mg) in DMF (2.0 mL) was added 2a (0.15 mmol, 26.1 mg), 2,2'-bipyridine (0.16 mmol, 25.0 mg) and the mixture was stirred at room temperature for a few min. Then the reaction was heated at 120 oC for 3.5 h. On cooling, the mixture was diluted with H2O, and extracted with ethyl ether. The extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with petroleum ether/ethyl acetate as eluent to afford the products 3da and 3da' in 49percent and 22percent yields, respectively. The data for 3da: m.p. 132-133 oC (literature2); 1H NMR (300 MHz, CDCl3): 8.46 (d, J = 8.1 Hz, 1H), 7.56 (d, J = 7.2 Hz, 1H), 7.44-7.20 (m, 12H), 2.0 (s, 3H); 13C NMR (75 MHz, CDCl3): 171.6, 136.7, 135.0, 133.0, 132.9, 131.6, 130.7, 130.0, 129.2, 128.6, 128.2, 126.9, 125.5, 123.8, 123.3, 119.5, 116.2, 27.9; IR (neat): 3054, 2962, 2919, 1695, 1611, 1488, 1444, 1368, 1348, 1303, 1221, 1183, 1155, 1128, 1104, 1075, 1022, 977, 930, 810, 777cm-1; MS (70 eV, EI) m/z (percent): 311, 269 (100), 254, 239, 213, 190, 165, 139, 89, 77, 63; HRMS Calcd for C22H17NO: 311.1310, found: 311.1315. The date for 3da': m.p. 114-116 oC (literature3); 1H NMR (300 MHz, CDCl3): 8.24 (brs, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.46-7.13 (m, 13H); 13C NMR (100 MHz, CDCl3): 135.9, 135.0, 134.1, 132.7, 130.1, 128.7, 128.6, 128.5, 128.1, 127.7, 126.2, 122.7, 120.4, 119.7, 115.0, 110.9; IR (neat): , 3057, 2963, 2923, 2851, 1601, 1553, 1505, 1485, 1456, 1440, 1424, 1371, 1305, 1329, 1262, 1179, 1155, 1095, 1071, 966, 800 cm-1; MS (70 eV, EI) m/z (percent): 269 (100), 254, 239, 226, 213, 190, 165, 133, 120, 106, 89, 77, 63; HRMS Calcd for C20H15N: 269.1204, found: 269.1201. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium iodide dihydrate; rhodium contaminated with carbon; sodium carbonate; In N,N-dimethyl-formamide; at 135℃; for 36h;Schlenk technique; | 1) In a pre-dried 50mL Schlenk reaction tube with a magneton, 0.3 mmol of aniline, 0.9 mmol of alkyne, 0.03 mmol of rhodium on carbon, 0.3 mmol of sodium carbonate,0.15mmol sodium iodide dihydrate were added and mixed evenly, 2) After adding 1.0 mL of dimethylformamide, the reaction tube was placed in a preheated 135 °C oil bath and the reaction was blocked for 36 hours; 3) Water and ethyl acetate were added to separate the organic phase, the solvent was removed on a rotary evaporator and passed through a column of silica gel to give the target product as a white solid. |
84% | With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride; In pentan-1-ol; at 100℃; for 24h; | The aniline 1a (55. 0muL, 0 . 6mmol), 1, 2-diphenyl 2a (71.3 mg, 0 . 4mmol), Cp*Rh (H2O)3(OTf)2(11.8 mg, 5mol percent), acetic anhydride (59. 0muL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100oC reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography get the pure product 2,3-diphenyl indole 3aa. The product is white solid, yield 70percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With lithium hydroxide monohydrate; C24H23N3O3PdS; In N,N-dimethyl-formamide; at 130℃; for 20h; | General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 molpercent of 5 in 2 mL N,N-dimethylformamide). The reaction mixture was stirred at 130 °C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 molpercent of catalyst 5 was applied. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; zinc trifluoromethanesulfonate; Trimethylacetic acid; In 1,2-dichloro-ethane; at 80℃; for 15h;Sealed tube; Inert atmosphere; | General procedure: Nitrones (0.2 mmol), diarylacetylenes (0.3 mmol), [Cp*RhCl2]2 (4 molpercent), AgSbF6 (16 molpercent), PivOH (2.0 equiv)and ethyl acetate (2 mL) were charged into the sealed tube. The reaction mixture was stirred at 80 °C for 15 h. After cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using triethylamine/PE or PE/EA to afford compounds 3. |