Structure of 13382-61-1
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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. : | 13382-61-1 |
Formula : | C9H6N2O3 |
M.W : | 190.16 |
SMILES Code : | O=[N+](C1=CC=C(C2=COC=N2)C=C1)[O-] |
MDL No. : | MFCD09032979 |
InChI Key : | STSISQMFQWBGLZ-UHFFFAOYSA-N |
Pubchem ID : | 14567797 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 50.76 |
TPSA ? Topological Polar Surface Area: Calculated from |
71.85 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.49 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.31 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.62 |
Solubility | 0.455 mg/ml ; 0.00239 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.96 |
Solubility | 0.209 mg/ml ; 0.0011 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.14 |
Solubility | 0.138 mg/ml ; 0.000726 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 |
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 |
-6.16 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 |
1.0 |
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) |
2.11 |
* 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 |
---|---|---|
42% | With sulfuric acid; nitric acid; at 0 - 20℃; for 1.16667h; | Reference Example 13: 4-(4-Nitrophenyl) oxazole. 4-Phenyloxazole (1 g, 6.89 mmol) was dissolved in concentrated sulfuric acid (5 mL) at 0 0C. A cold solution of nitrating-mixture (prepared by adding 3 mL cone, nitric acid to 5 mL of ice-cold cone, sulfuric acid) was added over 10 minutes. The mixture was allowed to warm to r.t. and stirred for Ih. The resulting solution was poured into ice-cold water giving a white precipitate, which was filtered and washed thoroughly with water. The solid was dissolved in DCM and washed with water then brine. The organic phase was dried over sodium sulfate and concentrated to yield 4-(4- nitro-phenyl)-oxazole (550 mg, 42%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; under 1520.1 Torr; for 16.0h;Inert atmosphere; | [00207] A solution of <strong>[13382-61-1]4-(4-nitrophenyl)oxazole</strong> (500 mg, 2.60 mmol) in MeOH:THF (6 mL; 1 : 1 mixture) was added 10% Pd/C (50 mg, 10% wt) under 2 atmosphere at room temperature. The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16h. Then, the reaction mixture was filtered over a pad of celite and the filtrate was concentrated under vacuum to afford crude compound. The crude compound was purified by FCC (eluent, 30% ethyl acetate in hexane) to afford 4-(oxazol-4-yl)aniline as a light brown viscous oil (260 mg, 62%). XH NMR (400 MHz, DMSO-i) delta 8.27-8.34 (m, 2H), 7.40-7.46 (m, 2H), 6.56-6.62 (m, 2H), 5.23 (s, 2H). ES-MS m/z 160.95 (M+H)+. |
62% | With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 16.0h;Inert atmosphere; | To a solution of <strong>[13382-61-1]4-(4-nitrophenyl)oxazole</strong> (500 mg, 2.60 mmol) in MeOH:THF (3:3 mL) was added 10% Pd/C (50 mg, 10% wt) under nitrogen atmosphere at room temperature. The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16h. Then, the reaction mixture was filtered over a pad of celite and the filtrate was concentrated under vacuum to afford crude compound. The crude compound was purified by FCC (eluent, 30% ethyl acetate in hexane) to afford 4-(oxazol-4-yl)aniline as a light brown viscous oil (260 mg, 62%).1H NMR (400 MHz, DMSO-d6) delta 8.27-8.34 (m, 2H), 7.40-7.46 (m, 2H), 6.56-6.62 (m, 2H), 5.23 (s, 2H). ES-MS m/z 160.95 (M+H)+. |
62% | With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 16.0h; | To a solution of <strong>[13382-61-1]4-(4-nitrophenyl)oxazole</strong> (500 mg, 2.60 mmol) in MeOH:THF (3:3 mL) was added 10% Pd/C (50 mg, 10% wt) under nitrogen atmosphere at room temperature. The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16h. Then, the reaction mixture was filtered over a pad of celite, and the filtrate was concentrated under vacuum to afford crude compound. The crude compound was purified by FCC (eluent, 30% ethyl acetate in hexane) to afford the title compound 4 as light brown thick liquid (260 mg, 62%).XH NMR (400 MHz, DMSO-i) delta 8.27-8.34 (m, 2H), 7.40-7.46 (m, 2H), 6.56-6.62 (m, 2H), 5.23 (s, 2H). ES-MS m/z 160.95 (M+H)+. |
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; ethanol; at 20℃; under 760.051 Torr; for 12.0h; | 5% Palladium-carbon powder was added to a suspension of <strong>[13382-61-1]<strong>[13382-61-1]4-(4-nitrophenyl)-1,3-oxazol</strong>e</strong> in mixture of ethanol and tetrahydrofuran, and the reaction mixture was stirred under 1 atm of hydrogen at ambient temperature for 12 hours. The reaction mixture was filtered through Celite, and the resulting filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography, to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS (M)+: 160. | |
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; ethanol; at 20℃; for 12.0h; | Reference Example 1: 5% Palladium-carbon powder was added to an ethanoltetrahydrofuran mixed suspension of <strong>[13382-61-1]4-(4-nitrophenyl)-1,3-oxazol</strong> and stirred for 12 hours at room temperature in a hydrogen atmosphere. The reaction solution was filtered through Celite and the filtrate was evaporated under reduced pressure. The resulting crude product is purified with a silica gel column chromatography to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS(M)+: 160. | |
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; ethanol; at 20℃; for 12.0h; | 5% Palladium-carbon powder was added to an ethanol-tetrahydrofuran mixed suspension of <strong>[13382-61-1]4-(4-nitrophenyl)-1,3-oxazol</strong> and stirred for 12 hours at room temperature in a hydrogen atmosphere. The reaction solution was filtered through Celite and the filtrate was evaporated under reduced pressure. The resulting crude product is purified with a silica gel column chromatography to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS(M)+. 160. | |
With iron; acetic acid; at 20℃; for 3.0h; | [0003431 To a stirred solution of compound 4 (0.7 g, 1 eq) in acetic acid (10 mL), Iron powder (2.063 g) was added in one portion and the reaction mixture was stirred at room temperature for 3 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated to dryness. The residue was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 25 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 30% EtOAc-hexane to afford the title compound 5. LCMS (mlz): 161.00 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 1.5h; | [000342j A stirred solution of compound 2 (1 g, 1 eq) in formamide 3 (2.55 g, 14.74 eq) was added at 130 C for 1.5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (2 X 50 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 4. ?H NMR (400 MHz, CDC13) oe: 8.29 (d, J= 8.8 Hz, 2H), 8.10 (s, 1H), 7.99 (s, 1H), 7.92 (d, J= 8.8 Hz, 2H). |
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