Structure of 859833-22-0
*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. : | 859833-22-0 |
Formula : | C18H28BNO2 |
M.W : | 301.23 |
SMILES Code : | CC1(C)C(C)(C)OB(C2=CC=C(C=C2)CN3CCCCC3)O1 |
MDL No. : | MFCD08271932 |
InChI Key : | HJKVRMHVLINDRH-UHFFFAOYSA-N |
Pubchem ID : | 18525779 |
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 potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 0.75h; | 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolane (250 mg; 0.84 mmol), piperidine (94 mg; 1.1 mmol) and K2CO3 (140 mg; 1.01 mmol) in DMF (4 ml) are heated to <n="59"/>800C for 45 minutes. The reaction mixture is cooled to room temperature, diluted with TBME, filtered and evaporated to dryness to deliver the title compound as orange crystals. N 1 H-NMR (400MHz; DMSO-d6): 7.63 (d, 2H); 7.33 (d, 2H); 3.44 s, 2H); 2.31 (bs, 4H); 1.50 (m, 4H); 1.39 (m, 2H); 1.30 (s, 12H). MS (m/z) ES+: 302 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 2.5h;Inert atmosphere; | General procedure: To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; for 0.75h;Inert atmosphere; Darkness; Reflux; | To a suspension of 18 (1.700g, 4.7mmol) in 3.5:1 DME/ H2O (18mL) under nitrogen, 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperidine (95%, 1.67g, 5.2mmol), NaHCO3 (1.18g, 14mmol), PdCl2(dppf)CH2Cl2 (0.139g, 0.19mmol) were added and the resulting mixture was refluxed for 45min. in the dark. After evaporation of the solvent the residue was added with water/ethyl acetate. The phases were separated. The organic layer was dried, filtered and evaporated to obtain 3.00g of crude. Purification by flash chromatography (CH2Cl2: MeOH 98:2) gave 1.9g (89%) of the title compound; mp 93C; 1H NMR (CDCl3) δ 10.26 (1H, t, J=4.4Hz); 8.01 (1H, d, J=4.0Hz); 7.97 (1H, d, J=8.2Hz); 7.70-7.60 (3H, m); 7.42 (2H, d, J=8.5Hz); 7.30 (2H, d; J=8.2Hz); 6.94 (2H, d, J=8.5Hz); 6.54 (1H, d, J=3.96Hz); 4.67 (2H, d, J=4.4Hz); 3.86 (3H, s); 3.52 (2H, s); 2.53-2.31 (4H, m); 1.72-151 (6H, m). Anal. Calcd for C28H30N4O2: C, 73.98; H, 6.65; N, 12.33. Found: C, 73.77; H, 6.61; N, 12.52. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 1.5h;Inert atmosphere; Microwave irradiation; | 4-(Piperidinomethyl)phenylboronic acid pinacol ester (131 .29mg, 0.44mmol) was added to a degassed solution of 3-iodo-1 -(3-piperidyl)pyrazolo[3,4-c ]pyrimidin-4-amine (l OO.Omg, 0.29mmol), potassium carbonate (80.32mg, 0.58mmol), and 1 ,1 '-bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (1 1 .87mg, O.OI OOmmol) in water (1 ml_) and 1 ,4-dioxane (6ml_). The reaction mixture was heated under microwave irradiation at 300W for 90 min at 120C. Upon completion, the solvent was removed under vacuum. The crude 1 -(3-piperidyl)-3-[4-(1 - piperidylmethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine (1 13.77mg, 0.29mmol) was added to a solution of acrylic acid (0.04ml_, 0.58mmol), /V-(3-dimethylaminopropyl)-/V-ethylcarbodiimide hydrochloride (EDCI) (1 1 1 .42mg, 0.58mmol), and triethylamine (0.12mL, 0.87mmol) in DCM (3ml_). The reaction mixture was left under constant stirring overnight at room temperature. The product was isolated and purified by prep LCMS (dissolved in 8:1 :1 DMSO:CH3CN:H20 in the presence of a strong acid modifier, which was TFA). LCMS (ES+, short acidic) 0.99 min, m/z 446.3 [M+H]+ NMR: 8.32 (bs, 1 H), 8.25 (s, 1 H), 7.75 (d, J 8.1 Hz, 2H), 7.19 (d, J, 8.1 Hz, 2H), 6.60 ( m, 1 H), 6.31 (m, 1 H), 5.51 (m, 1 H), 4.90 (m, 1 H), 4.51 (m, 1 H), 4.21 (s, 2H), 4.01 (m, 1 H), 3.78 (m, 2H), 3.43 (m, 1 H), 3.15 (m, 5H), 2.31 (m, 2H), 1 .48 (m, 5H), 1 .17 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water;Inert atmosphere; Heating; | General procedure: To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 150℃; for 0.25h;Inert atmosphere; Microwave irradiation; Sealed tube; | General procedure: To a mixture of derivative of type IV (50 mg, 0.147 mmol) intoluene (1.5 mL) and EtOH (0.75 mL) were successively added thedesired boronic ester or acid of type V (0.176 mmol, 1.2 eq.), K2CO3(0.294 mmol, 2.0 eq.) and Pd(PPh3)4 (0.0147 mmol, 10 mol %). Thereaction mixture was degassed with Ar and irradiated under microwavefor 20 min at 150 C. Alternatively PdCl2(dppf) 10 mol %,could be used as catalyst. In this case the base was switched toNa2CO3 (2.0 eq.) and the irradiation performed for 40 min at 100 C.In both cases, after cooling, the volatiles were removed underreduced pressure and the crude material purified by flash chromatography(CH2Cl2/MeOH 80/20 NH4OH 0.1 mL). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 150℃; for 0.25h;Inert atmosphere; Microwave irradiation; Sealed tube; | General procedure: To a mixture of derivative of type IV (50 mg, 0.147 mmol) intoluene (1.5 mL) and EtOH (0.75 mL) were successively added thedesired boronic ester or acid of type V (0.176 mmol, 1.2 eq.), K2CO3(0.294 mmol, 2.0 eq.) and Pd(PPh3)4 (0.0147 mmol, 10 mol %). Thereaction mixture was degassed with Ar and irradiated under microwavefor 20 min at 150 C. Alternatively PdCl2(dppf) 10 mol %,could be used as catalyst. In this case the base was switched toNa2CO3 (2.0 eq.) and the irradiation performed for 40 min at 100 C.In both cases, after cooling, the volatiles were removed underreduced pressure and the crude material purified by flash chromatography(CH2Cl2/MeOH 80/20 NH4OH 0.1 mL). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16.0h; | A stirred mixture of 4-bromo-2,7-bis(3- morpholinopropyl)-9-((2-(pyrrolidin-1 - yl)ethyl)amino)benzo[lmn][3,8]phenanthroline- 1 ,3,6,8(2H,7H)-tetraone (155 mg, 0.218 mmol) and 1 -(4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)benzyl)piperidine (197 mg, 0.653 mmol) in dioxane (4 mL) was treated with potassium carbonate (436 mL ef a 2 M aq selutien, 0.871 mmol) and de-gassed. S-Phos (0122) Pd G3 (5.10 mg, 6.53 mmol) was charged, the mixture again de-gassed and the whole heated to 80 C. After 16 hr, the mixture was allowed to cool then diluted with water (10 mL) and sat aq NaHCO3 (10 mL) and extracted with DCM (2 x 20 mL). The combined organics were dried ever Na2SO4 and evaperated. Column chromatography (12 g RediSep Gold, 30-60% (9:1 DCM: 0.7 M NH3 in MeOH) in DCM, leading in DCM) gave product in moderate purity. The residue was purified by reverse phase cclumn chrcmatcgraphy (12 g Reveleris C-18, 75- 100% (70 mM NH3 in MeOH) in water, leading in DMSO) tc afferd the product as a bright red glassy sclid (61 mg, 35%). (0123) LCMS: Found m/z 806.3: (C46H6oN706 (MH+) requires 805.5) 7.38 min. 1 H NMR (500 MHz, Methylene Chlcride-d2) d 10.25 (t, J = 5.1 Hz, 1 H), 8.47 (s, 1 H), 8.34 (s, 1 H), 7.43 (d, J = 8.1 Hz, 2H), 7.33 (d, J = 8.1 Hz, 2H), 4.29 (t, J = 7.4 Hz, 2H), 4.14 (t, J = 7.3 Hz, 2H), 3.75 (q, J = 5.9 Hz, 2H), 3.64 - 3.50 (m, (0124) 10H), 2.95 (t, J = 6.2 Hz, 2H), 2.69 - 2.66 (m, 4H), 2.56 - 2.29 (m, 16H), 1.93 (p, J = 7.0 Hz, 2H), 1.89 - 1.82 (m, 6H), 1.68 - 1.62 (m, 4H), 1.53 - 1.49 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; | General procedure: To a solution of compound 1b-2 (1 g, 3.92 mmol) in DMF (20 mL) was added compound Pd(dppf)Cl2 (144 mg, 0.19 mmol), compound 1b.2 (1.2 g, 3.33 mmol) and potassium acetate (570 mg, 5.8 mmol), the mixture was stirred under argon atmosphere at 80 C. overnight. The reaction solution was concentrated and purified by combiflash to give compound 1b (400 mg, 31%). MS m/z (ESI): 304 [M+H]+. |
A190256 [859833-21-9]
1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine
Similarity: 0.98
A201743 [1073372-05-0]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine hydrochloride
Similarity: 0.98
A573417 [1315278-37-5]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)azepane
Similarity: 0.98
A640803 [1021186-08-2]
1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine hydrochloride
Similarity: 0.97
A922449 [884507-39-5]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)pyrrolidine
Similarity: 0.95
A190256 [859833-21-9]
1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine
Similarity: 0.98
A201743 [1073372-05-0]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine hydrochloride
Similarity: 0.98
A573417 [1315278-37-5]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)azepane
Similarity: 0.98
A640803 [1021186-08-2]
1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine hydrochloride
Similarity: 0.97
A922449 [884507-39-5]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)pyrrolidine
Similarity: 0.95
A190256 [859833-21-9]
1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine
Similarity: 0.98
A201743 [1073372-05-0]
1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine hydrochloride
Similarity: 0.98
A640803 [1021186-08-2]
1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine hydrochloride
Similarity: 0.97