Structure of 365564-07-4
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 365564-07-4 |
Formula : | C14H21BO4 |
M.W : | 264.13 |
SMILES Code : | COC1=CC(=CC(OC)=C1)B1OC(C)(C)C(C)(C)O1 |
MDL No. : | MFCD05865191 |
InChI Key : | CZYHRTIJLUONKY-UHFFFAOYSA-N |
Pubchem ID : | 16217660 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.57 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 75.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
36.92 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 |
2.85 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.0 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.9 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.57 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.31 |
Solubility | 0.13 mg/ml ; 0.000491 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.28 |
Solubility | 0.137 mg/ml ; 0.00052 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.25 |
Solubility | 0.0147 mg/ml ; 0.0000557 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) |
Yes |
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 |
-5.89 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.13 |
* 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 |
---|---|---|
99% | With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole; at 100℃; for 16h;Inert atmosphere; | The Examples milligrams Preparation of 3,5-dimethoxybenzene boronic acid pinacol ester, specifically including the steps of: nitrogenEnvironment, the reaction flask was added 1,3-dimethoxybenzene (69.1mg, 0.5mmol),CoupletBoronic acid pinacol ester(126.9mg, 0.5mmol, of formula (5)),Methoxy-1,5-cyclooctadiene iridium dimer(3.4mg, 0.005mmol, 1%, formula (6)),Borane pyridine ligands ago(4.0mg, 0.01mmol, 2%, of Formula (1))And cyclopentyl methyl ether(1mL, 1,3-dimethoxybenzene reaction concentration is 0.5mol / L),The reaction at 100 16h; the reaction was completed by rotary evaporation (20 ~ 40 ) removing the solvent (cyclopentyl methyl ether), was purified by columnChromatography (using 200-300 mesh size silica gel, substance to be purified by silica gel ratio of 50 to 100: 1, eluent stoneOleyl ether and ethyl acetate, the volume ratio 20 ~ 50: 1) to afford the product to give a colorless 3,5-dimethoxybenzene boronic acid pinacol ester solid(125mg, 99%), |
90% | With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole; at 100℃; for 3h;Schlenk technique; Inert atmosphere; Sealed tube; | General procedure: B2pin2, [IrCl(COD)]2 (1.0 mol%), preligand 1 (2.0 mol%), and (hetero)arene (0.2 mmol, ifsolid) were placed in a dried Schlenk flask (15 mL in volume) equipped with a stirring bar. Afterevacuating and refilling the flask with dry nitrogen three times, (hetero)arene (0.2 mmol, if liquid)and methoxycyclopentane (CAPE, 0.5 mL) were added with syringes under a stream of nitrogen.The resulting mixture was stirred at the corresponding temperature for the assigned time. After cooling to room temperature, the reaction mixture was concentrated and then purified by columnchromatography on silica gel to give the target product (The spectra data for the borylated compoundscan be seen in the Supplementary Material). |
68.4% | With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In cyclohexane; at 20℃;Inert atmosphere; | 1523.6 mg (6 mmol) of pinacol diboronate (B2pin2), 132.6 mg of [Ir (0 Torr) (COD)] and 107.4 mg (0.30 mmol) of 4,4-di-tert-butyl linkage Into 15 mL of cyclohexane, add dtbpy, protect with N2, stir at room temperature, and add 1.22 mL of 1,3-dimethoxybenzene while stirring. Stir the reaction for 10 h. Evaporate the solvent and purify by column chromatography. Petroleum ether: Elution with ethyl acetate (V:V=5:1), dried to give 1083.4 mg of compound 3 with a yield of 68.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 160℃; for 0.166667h;Microwave irradiation; | to a solution of LG2-101 (32 mg, 0.119 mmol), 2-(3,5- dimethoxyphenyl)-(4,4,5,5-tetramethyl-l,3,2-dioxaborolane (47 mg, 0.178 mmol, 1.5 equiv.) and Tetrakis(triphenylphosphine)-palladium(0) (16 mg, 0.013 mmol) in THF (1.0 ml) was added 0.5 ml of aqueous 1 N K2CO3 solution. The resultant mixture was heated at 160 0C under microwave irradiation for 10 min. The mixture was diluted with EtOAc, and the organic phase was separated out. After removal of solvent, the residue was subjected to flash column chromatography on silica gel (elution with hexane-EtOAc) to yield LG2-102 as a white gel (16 mg, 41%). ESI-MS: m/z 325 (M+l); IH NMR (600 MHz, CDC13): delta 7.60 (IH, d, J= 4.8 Hz), 7.55 (IH, s), 7.36 (IH, d, J= 4.8 Hz), 6.673 (IH, s), 6.670 (IH, s), 6.53 (IH, s), 6.14 (IH, t, J= 5.4 Hz, NH), 3.85 (6H, s), 3.46 (2H, dd, J= 5.4, 12.0 Hz), 1.18 (IH, m), 0.59 (2H, m), 0.32 (2H, m); 13C NMR (150.9 MHz, CDC13): delta 161.41, 149.54, 133.76, 130.59, 130.47, 129.07, 128.25, 107.78, 106.16, 100.37, 55.54, 45.84, 10.71, 3.62. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.9% | EXAMPLE 21 4-amino-8-(3,5-dimethoxyphenyl)-N-propyl-cinnoline-3-carboxamide Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (100 mg, 0.33 mmol) and 2-(3,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-(1,3,2)-dioxaborolane (256 mg, 0.97 mmol) were reacted to afford the title compound (110 mg, 93.9% yield) as an off-white solid. 1H NMR (300 MHz, CDCl3) delta 8.57 (br, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.79 (dd, J=7.2 Hz, J'=1.3 Hz, 1H), 7.71 (t, J=7.7 Hz, 1H), 6.79 (d, 3H), 3.83 (s, 6H), 3.47 (q, J=6.7 Hz, 2H), 1.67 (m, J=7.3 Hz, 2H), 1.01 (t, J=7.4 Hz, 3H) MS APCI, m/z=367 (M+H) HPLC 1.98 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; at 125℃; for 1h; | A mixture of ethyl 4-chloro-5-(4-fluorophenyl)-6-methyl-3-pyridinecarboxylate (i.e. the product of Step C) (1.5 g, 5.7 mmol), 2-(3,5-dimethoxyphenyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (2.42 g 9.17 mmol), potassium phosphate (2.43 g, 11.5 mmol), palladium acetate (0.047 g, 0.21 mmol) and 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl was heated at 125 0C for 1 h. The reaction mixture was cooled, dichloromethane was added and the layers were separated. The organic layer was washed with water and concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (10 to 40% ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a white solid (1.0 g).1H NMR (CDCl3): delta 8.91 (s, IH), 6.96 (m, 4H), 6.26 (t, IH), 6.07 (d, 2H), 4.10 (q, 2H), 3.63 (s, 6H), 2.40, (s, 3H), 1.02 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With potassium phosphate; tris-(o-tolyl)phosphine;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 20℃; for 16h;Sealed; Inert atmosphere; | A sealed degassed mixture of 3,5-dimefhoxyphenylboronic acid pinacol ester (50 mg, 0.177 mmol), teri-butyl-bromoacetate (22 mu, 0.148 mmol), P(o-tol)3 (4.1 mg, 0.0133 mmol),Pd2(dba)3 (4.1 mg, 0.0044 mmol), K3PO4 (157 mg, 0.739 mmol) in THF (3 mL) under argon was stirred at room temperature for 16 h. The reaction mixture was diluted with 20 mL of Et20 and then washed with brine. The reaction mixture was dried with MgSC , dried under reduced pressure and purified by flash chromatography to give tert-butyl 2-(3,5-dimethoxyphenyl)acetate as a yellow liquid (18 mg, 48%). NMR (400 MHz, CDCh) delta 6.43 (d, J = 2.0 Hz, 2 H), 6.36 (t, J = 2.3 Hz, 1 H), 3.78 (s, 6 H), 3.45 (s, 2 H), 1.44 (s, 9 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; N,N-dimethyl-formamide; at 110℃; for 0.5h;microwave irradiation; | A mixture of 1 ,1 -dimethylethyl 4-(3-bromo-4-[(3-chlorophenyl)sulfonyl]amino}-6- methylthieno[2,3-6]pyridin-2-yl)-1 /-/-pyrazole-1 -carboxylate (Description 75) (100 mg, 0.171 mmol), <strong>[365564-07-4]3,5-dimethoxyphenylboronic acid pinacol ester</strong> (90 mg, 0.343 mmol), potassium carbonate (95 mg, 0.685 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.96 mg, 3.43 muetaetaomicronIota) were weighed into a microwave vial. 1 ,4-Dioxane (1.5 mL), DMF (0.75 mL) and water (0.38 mL) were added and the mixture heated in a microwave at 1 10C for 30 min. At this point, both reaction mixtures were combined and concentrated. The residue was passed through an SCX cartridge, eluting with MeOH (75 mL) and then with 2M NH3 in MeOH (100 mL). The basic methanolic solution was concentrated and purified by MDAP (acidic conditions), to give the title compound (45 mg). LCMS (A) m/z: 541 [M+1]+, Rt 1 .26 min (acidic). |
A254430 [325142-84-5]
2-(3-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.98
A112414 [171364-79-7]
2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.97
A176799 [864772-18-9]
4,4,5,5-Tetramethyl-2-(3-phenoxyphenyl)-1,3,2-dioxaborolane
Similarity: 0.96
A193794 [365564-10-9]
2-(3,4-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.94
A117971 [269410-26-6]
4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane
Similarity: 0.94
A254430 [325142-84-5]
2-(3-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.98
A112414 [171364-79-7]
2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.97
A176799 [864772-18-9]
4,4,5,5-Tetramethyl-2-(3-phenoxyphenyl)-1,3,2-dioxaborolane
Similarity: 0.96
A193794 [365564-10-9]
2-(3,4-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.94
A117971 [269410-26-6]
4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane
Similarity: 0.94
A254430 [325142-84-5]
2-(3-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.98
A112414 [171364-79-7]
2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.97
A176799 [864772-18-9]
4,4,5,5-Tetramethyl-2-(3-phenoxyphenyl)-1,3,2-dioxaborolane
Similarity: 0.96
A193794 [365564-10-9]
2-(3,4-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.94
A117971 [269410-26-6]
4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane
Similarity: 0.94