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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 126726-62-3
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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.
4.5
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CAS No. : | 126726-62-3 |
Formula : | C9H17BO2 |
M.W : | 168.04 |
SMILES Code : | C=C(B1OC(C)(C)C(C)(C)O1)C |
MDL No. : | MFCD08276843 |
InChI Key : | SVSUYEJKNSMKKW-UHFFFAOYSA-N |
Pubchem ID : | 10997426 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H315-H319 |
Precautionary Statements: | P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.78 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.85 |
TPSA ? Topological Polar Surface Area: Calculated from |
18.46 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 |
2.68 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.07 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.12 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.41 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.5 |
Solubility | 0.526 mg/ml ; 0.00313 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.72 |
Solubility | 0.32 mg/ml ; 0.00191 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.31 |
Solubility | 0.831 mg/ml ; 0.00494 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) |
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 |
-5.42 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 |
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) |
3.18 |
* 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 |
---|---|---|
470 mg | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; at 80℃; for 4h;Inert atmosphere; | Synthesis of 4-fluoro-l-nitro-2-(prop-l-en-2-yl) benzene [0471] To a stirred solution of 2-chloro-4-fluoro-l -nitrobenzene (500 mg, 2.84 mmol) in 1, 4-dioxane (12 mL) under argon atmosphere were added 4, 4, 5, 5-tetramethyl-2-(prop-l- en-2-yl)-l, 3, 2-dioxaborolane (569 mg, 3.39 mmol), sodium carbonate (359 mg, 3.39 mmol), water (2.8 mL) at RT and purged under argon for 10 min. Pd(PPh3)2Cl2 (157 mg, 0.22 mmol) was then added to the reaction mixture and heated at 80 C for 4 h. After consumption of the starting materials (monitored by TLC), the reaction was filtered and the filtrate was concentrated in vacuo. The residue was diluted with water (50 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford 4-fluoro-l-nitro-2-(prop-l-en-2-yl) benzene (470 mg) as an off-white solid. LCMS: 182 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.81 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 5% EtOAc/hexanes (R/. 0.6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere; | To a 500 mL round-bottomed flask were added <strong>[53312-82-6]4-amino-2-bromobenzonitrile</strong> (7.00 g, 35.5 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (6.87 g, 40.9 mmol), potassium carbonate (9.82 g, 71.1 mmol), followed by 1,4-dioxane (90 mL), water (45 mL) and PdCl2(dppf)-CH2Cl2 (0.087 g, 0.107 mmol). Argon was bubbled through the suspension and the flask was sealed and heated at 80 C overnight. The reaction mixture was diluted with EtOAc, washed with brine and the organic layer was separated, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient from 0 to 50% of a 10% solution of 2 N ammonia in methanol in ethyl acetate in DCM to afford 4-amino-2-(prop- l-en-2-yl)benzonitrile (5.23 g, 33.1 mmol, 93% yield). ES [MS] m/z: 159.12 [M+H]+. NMR (400 MHz, CDCh) delta 7.47-7.42 (m, 1H), 6.58 (dq, J=4.5, 2.4 Hz, 2H), 5.33 (quin, J=1A Hz, 1H), 5.26-5.22 (m, 1H), 4.22-4.09 (m, 2H), 2.17 (dd, J=1.5, 1.0 Hz, 3H), 1.31-1.29 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 3.0h;Inert atmosphere; | A mixture of <strong>[438554-45-1]4-chloro-5-nitro-2-(trifluoromethyl)pyridine</strong> (500 mg, 2.21 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (0.41 g, 2.43 mmol), Pd(dppf)Cl2 (0.16 g, 0.22 mmol) and K2C03 (0.76 g, 5.52 mmol) in l,4-dioxane (8 mL) and H20 (2 mL) were stirred at 80C for 3 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated. The crude residue was purified by silica gel column (0- 10% EtOAc in petroleum ether) to give 5-nitro-4-(prop-l-en-2-yl)-2-(trifluoromethyl)pyridine (420 mg, yield: 82%) as a light yellow solid. 1H NMR (400 MHz, CDCl3) 5 = 9.12 (s, 1H), 7.69 (s, 1H), 5.40 (s, 1H), 5.15 (s, 1H), 2.14 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Preparation 34A methyl 5-fluoro-2-(prop-1-en-2-yl)isonicotinate A mixture of <strong>[885588-14-7]methyl 2-bromo-5-fluoroisonicotinate</strong> (900 mg, 3.85 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (712 mg, 4.24 mmol), Pd(Amphos)Cl2 (272 mg, 0.0385 mmol) and K2CO3 (1.6 g, 11.6 mmol) in toluene (15 mL) and MeOH (10 mL) was stirred at 65 C. for 2 hours under nitrogen atmosphere. After cooled to rt, the resulting mixture was filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EA=20/1) to afford methyl 5-fluoro-2-(prop-1-en-2-yl)isonicotinate (510 mg, 68%) as a yellow oil. MS ESI calculated for C10H10FNO2 [M+H]+, 196.07, found 196.00. |
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