Structure of 1093307-35-7
*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. : | 1093307-35-7 |
Formula : | C11H16BN3O2 |
M.W : | 233.08 |
SMILES Code : | N#CCN1N=CC(B2OC(C)(C)C(C)(C)O2)=C1 |
MDL No. : | MFCD18383259 |
InChI Key : | LBHVFQPLKQHEQF-UHFFFAOYSA-N |
Pubchem ID : | 67468095 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 20℃; for 6h; | A vial was charged with Example 271A (0.682 g, 2.93 mmol), Example 271B (1.25 g, 2.44 mmol), cesium carbonate (1.99 g, 6.10 mmol), 1,4-dioxane (12.5 mL) and water (2.50 mL). After a vacuum/nitrogen purge through a septa, tris(dibenzylideneacetone)dipalladium(0) (0.112 g, 0.122 mmol) and tri-^-butylphosphonium tetrafluoroborate (0.085 g, 0.29 mmol) were added and a cap was put on the vial after flushing with nitrogen. After about 6 hours at ambient temperature, the reaction was <n="164"/>partitioned between saturated aqueous sodium bicarbonate and dichloromethane (50 mL each). The layers were separated and the aqueous layer was extracted with additional dichloromethane (2 x 50 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude oil was dissolved in a minimal amount of dichloromethane and purified via silica gel chromatography eluting with a gradient of 20-60% ethyl acetate in heptane to afford the title compound. 1H NMR (400 MHz, DMSOd6) delta ppm 8.43 (s, IH), 8.19 (s, IH), 8.08 (d, J = 9.22 Hz, IH), 7.93 (m, 2H), 5.53 (s, 2H), 1.67 (s, 9H), 1.39 (s, 18H). MS (ESI+) m/z 539.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium carbonate; sodium iodide; In acetonitrile; at 70℃; | A mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)- lH- pyrazole (0.50 g, 2.58 mmol), sodium iodide (39 mg, 0.26 mmol) bromoacetonitrile (1 .3 g, 10.8 mmol) and potassium carbonate (1.0 g, 7.8 mmol) in acetonitrile (10 mL) was heated at 70 C overnight. Water was added and the solution was extracted with EtOAc (3x). The organic was dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography ( 10% to 100% EtOAc/hexane) to obtain 2-(4-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)-lH-pyrazol-l-yl)acetonitrile (0.38g, 63% yield). MS (ESI) m/z: 234.1 (M+H+). |
39% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 24h; | A solution of 4-(4,4, 5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H- pyrazole (5.11 g, 26.3 mmol) in DMF (50 mL) was treated with bromoacetonitrile (2.20 mL, 31.6 mmol) and K2CO3() (5.46 g, 39.5 mmol). The resulting suspension was stirred for 24 h at 100 C. The reaction mixture was cooled to ambient temperature, diluted with water (100 mL) then extracted with EtOAc (3 x 250 mL). The combined organic extracts were washed with water (3 x 50 mL) and brine (50 mL) then dried over anhydrous Na2SO4(). Following filtration, the organic extracts were concentrated under vacuum then purified by silica chromatography (10-60% Hexanes/EtOAc as the gradient eluent) to afford the title compound (2.42 g, 39% yield). ?H NIVIR (400 MHz, DMSO-d6) 8.04 (s, 1H), 7.71 (s, 1H), 5.49 (s, 2H), 1.25 (s, 12H). |
With potassium carbonate; sodium iodide; In acetonitrile; at 70℃; for 24h; | [00769] Compound 48 was prepared in 2 steps according to the following procedures: 4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazole (2.61 mmol, 1.0 equiv), bromoacetonitrile (4.2 equiv), sodium iodide (0.1 equiv) and potassium carbonate (3.0 equiv) were suspended in acetonitrile (10 mL) and heated to 70 C for 24h after which the reaction was cooled, partioned between water and brine and extracted with ethyl acetate. The combined organics were concentrated onto silica gel (4g) and purified using flash silica gel chromatography (Silicycle Si-40g, gradient 10-100% ethyl acetate/hexanes) to provide pinacol ester 47.47 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | N-(4-(3-Bromopyridin-4-yloxy)-2,5-difluorophenyl)-l-(4-fluorophenyl)-2-oxo-l ,2- dihydropyridine-3-carboxamide (0.1 19 g, 0.231 mmol) was combined with 2-(4-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)- l H-pyrazol- l-yl)acetonitrile (0.054 g, 0.23 1 mmol) and potassium carbonate (0.096 g, 0.692 mmol) in dioxane (4 mL) and water (0.667 mL), sparged with argon for several minutes, treated with tetrakis(triphenylphosphine)palladium(0) (0.013 g, 0.012 mmol) and heated to 85 C overnight. The mixture was cooled to room temperature, treated with saturated NaHC03 and extracted with EtOAc (2x). The combined organics were washed with brine, dried over MgS04 and concentrated to dryness. The crude material was purified over silica gel (40-100% EtOAc/Hex) to afford N-(4-(3-(l -(cyanomethyl)-l H-pyrazol-4- yl)pyridin-4-yloxy)-2,5-difluorophenyl)- l -(4-fluorophenyl)-2-oxo- l ,2-dihydropyridine-3- carboxamide (30 mg, 24% yield) as an off-white solid. NMR (400 MHz, DMSO-c¾: delta 12.45 (s, 1 H); 8.91 (s, 1 H); 8.61 (dd, J = 7.4, 2.1 Hz, 1 H); 8.55 (m, 1 H); 8.44 (s, 1 H); 8.29 (d, J = 5.7 Hz, 1 H); 8.24 (s, 1 H); 8.16 (dd, J = 6.6, 2.2 Hz, 1 H); 7.67 (dd, J = 1 1.0, 7.3 Hz, 1 H); 7.60 (dd, J = 8.7, 4.9 Hz, 2 H); 7.42 (t, J = 8.7 Hz, 2 H); 6.75 (m, 2 H); 5.54 (s, 2 H); MS (ESI) m/z: 543.1 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[00770] Compound 4 (0.11 mmol, 1.0 equiv) was dissolved in 2 mL dioxane/water (4:1 v/v) and charged with pinacol ester 47 (2.0 equiv) and sodium carbonate (5 equiv). The mixture was bubbled with Argon for 10 mm after which PdC12(dppf)-CH2C12 adduct (10 mol%) was added and the reaction was sealed and heated to 85 C for 20h. The mixture was then partioned between methylene chloride and water. The aqueous phase was extracted with methylene chloride (2x), dried over Na2SO4 and concentrated. The crude residue was purified using flash silica gel chromatography (Interchim Si-25g-30p, gradient of 0-50% acetone/methylene chloride) to provide compound 48. ESI-MS mlz: 530.3 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium hexamethyldisilazane; In tetrahydrofuran; at 0℃; for 1h; | A cold (0 C) solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetonitrile (2.42 g, 10.4 mmol) in THF (26 mL) was treated with iodomethane (1.94 mL, 31.1 mmol) then drop-wise with sodium bis(trimethylsilyl)amide (22.8 mL, 22.8 mmol). The resulting mixture was stirred 1 h at 0 C before quenching with the addition of saturated NH4C1(aq) (25 mL). At ambient temperature the reaction mixture was then partitioned between EtOAc (250 mL) and water (100 mL). The organic extracts were washed again with water (50 mL) and brine (50 mL), then dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The crude residue was purified by silica chromatography (5-50%, Hexanes/EtOAc as the gradient eluent) to afford the title compound (1.35 g, 50% yield). ?H NIVIR (400 MHz, DMSO-d6) 8.20 (s, 1H), 7.75 (s, 1H), 1.97 (s, 6H), 1.26 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In tetrahydrofuran; water; for 1h;Reflux; Inert atmosphere; | A flask is charged with Int 42 (50 mg, 0.11 mmol, 1 eq.), CS2CO3 (107 mg, 0.33 mmol, 3 eq.) 2- (1386) (4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazol-l-yl)acetonitrile (CAS 1093307-35-7; 33 mg, 0.14 mmol, 1.3 eq.) and THF/water solvent mixture: 9/1 (3 mL). The mixture is heated to reflux, degassed with N2 for 5 min, before Pd(dppf)Cl2-DCM (9 mg, 0.01 mmol, 0.1 eq.) is added. The mixture is stirred to reflux for 1 h. The mixture is partitioned in DCM and water and the aqueous layer is extracted with DCM. The combined organic layers are dried by filtration over hydrophobic column, concentrated in vacuo and purified by flash chromatography on silica gel (eluting with DCM/MeOH 95/5). A trituration in isopropylic ether and few drops of ACN then filtration affords the expected compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In 1,4-dioxane; water; at 90 - 100℃;Inert atmosphere; Sealed tube; | General procedure: A flask is charged with appropriate intermediate (1 eq.) and dioxane/water solvent mixture 4/1. The mixture is degassed with N2 then boronic ester (1.2 to 1.5 eq.), CS2CO3 (2 eq.), and Pd catalyst (Pd(dppf)Cl2-DCM 0.1 eq., or PdiPPIvp 0.15 eq.) are added. The flask is sealed and the mixture is heated to 90 C-l00 C for 1 h-l.5 h. The reaction mixture is quenched with water or a saturated NaHC03 solution, extracted with EtOAc or DCM. The combined organic layers are dried over anhydrous Na2S04, filtered or washed with brine and dried by filtration over hydrophobic column then concentrated in vacuo, purified by flash chromatography on silica gel and optionally dissolved in DCM and submitted to SPM32 3-mercaptopropyl ethyl sulfide silica treatment to afford the expected compound. |