Structure of 819849-22-4
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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. : | 819849-22-4 |
Formula : | C9H14BNO2 |
M.W : | 179.02 |
SMILES Code : | OB(C1=CC=CC(CN(C)C)=C1)O |
MDL No. : | MFCD03425961 |
InChI Key : | OFYQEYPITRRCBP-UHFFFAOYSA-N |
Pubchem ID : | 20672259 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
* 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 dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; at 100.0℃; for 16.0h;Inert atmosphere; | Example 9:3?-((Dimethylami no)methyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)ami no)-4-tI uoro-N-((1 -methyl-3-oxo-2,3,5,6,7,8-hexahydroisoqui fbI n-4-yl)methyl)-[1 , 1?- bi phenyl]-3-carboxamideThe compound of example 7 (80 mg, 0.154 mmol), (3- ((dimethylamino)methyl)phenyl)boronic acid (33.0 mg, 0.184 mmol), Na2003 (48.9mg, 0.461 mmol) was dissolved and stirred in dioxane with argon purging for 20 mm, followed by addition of PdCI2(dppf)CH2CI2 adduct (12.55 mg, 0.015 mmol) and continued purging of argon for 10 mm. The reaction mixture was heated at 100 00 for 16 h. After completion of the reaction, the crude material was absorbed on silica (100-200 mesh) and purified using column chromatography (silica gel, 10-15% methanol in chloroform) to yield the title compound.Yield: 41 mg (46.5 %); 1H NMR (DMSO-d6, 300 MHz): 6 0.907-0.953 (t, 3H), 1.640 (m, 7H), 2.108 (5, 3H), 2.379 (5, 6H), 2.741 (m, 2H), 3.188 (m, 2H),3.211(m, 2H), 3.848 (m, 3H),4.331 (m, 2H), 7.382-7.651 (m, 5H), 8.319 (5, 1H),8.330 (bs, 1 H), 11 .540 (bs, 1 H); MS (ES 1+): m/z 575.4 [M+H] HPLC Purity: 89.280/0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.3% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 80.0℃; for 10.0h; | 6-methoxy-2-chloro-3-iodoquinoline (400 mg, 1.25 mmol)Was dissolved in 3 mL of toluene, Pd(PPh3)4 (37 mg, 0.033 mmol) was added successively, Of sodium carbonate (212 mg, 2.00_31) in 0.3 ml of water, <strong>[819849-22-4]3-dimethylaminomethylbenzeneboronic acid</strong> (269 mg, 1.50 mmol), 80 C stirring reaction for 10 hours,(20mL * 3), and the organic phase was separated and purified by column chromatography (dichloromethane / methanol 15: 1).To obtain 312 mg of a light yellow solid, yield: 76.30% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.52% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 80.0℃; for 8.0h; | 2-Chloro-3-iodoquinoline (100 mg, 0.346 mmol) was dissolved in 3 mL of toluene, Followed by Pd (PPh3) 4 (12 mg, 0.01 mmol)Aqueous solution of sodium carbonate (73 mg, 0.692 mmol) in 0.3 mL of water,<strong>[819849-22-4]3-dimethylaminomethylbenzeneboronic acid</strong> (124 mg, 0.692 mmol),The reaction mixture was stirred at 80 C for 8 hours. To the residue was added 5 mL of water and extracted with dichloromethane (10 mL * 3). The organic phases were combined and purified by column chromatography (dichloromethane / methanol 20: 1)To give 91 mg of a pale yellow oil, yield 88.52% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.78% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 80.0℃; for 10.0h; | 2-chloro-6-bromo-3-iodoquinoline (600 mg, 1.64 mmol) was dissolved in 3 mL of toluene, Pd(PPh3)4 (37 mg, 0.033 mmol) was added successively,Sodium carbonate (260 mg, 2.45 mmol) in 0.3 mL of water,<strong>[819849-22-4]3-dimethylaminomethylbenzeneboronic acid</strong> (440 mg, 2.45 mmol),The reaction mixture was stirred at 80 C for 10 hours. To the residue was added 20 mL of water and extracted with dichloromethane (20 mL * 3). The organic phase was combined and purified by column chromatography (dichloromethane / methanol 15: 1)To obtain 520 mg of a light yellow solid, yield 84.78% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With pyridine; copper diacetate; In methanol; at 25.0℃; for 80.0h; | Add 2-chloro-7H-pyrrolo [2,3-d] pyrimidine (200 mg, 1.33 mmol) and3-((dimethylamino) methyl) phenylboronic acid (561mg, 2.60mmol) was dissolved in methanol (10mL),Copper acetate (787.92 mg, 3.91 mmol) and pyridine (420.47 mg, 5.21 mmol) were added, and the reaction was left open at 25 C for 80 hours.The reaction solution was poured into water and extracted with ethyl acetate. The organic phases were combined,It was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered.The filtrate was concentrated, and the residue was purified by preparative thin layer chromatography (eluent: petroleum ether / ethyl acetate = 1/2),The title compound (50 mg, yield: 6.0%) was obtained in this step. |