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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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Search for reports by entering the product batch number.
    							Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
    							Batch number can be found on the product's label following the word 'Batch'.
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| CAS No. : | 57002-01-4 | 
| Formula : | C8H15BO2 | 
| M.W : | 154.01 | 
| SMILES Code : | OB(/C=C/C1CCCCC1)O | 
| MDL No. : | MFCD01074615 | 
| 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.

 [ 57002-01-4 ]
                                                    
                                                    [ 57002-01-4 ]


 [ 929078-65-9 ]
                                                    
                                                    [ 929078-65-9 ]
 [ 57002-01-4 ]
                                                    
                                                    [ 57002-01-4 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 90℃; for 6.5h; | Preparation of 1-[3-((E)-2-cyclohexylvinyl)pyrido[2,3-b]pyrazin-6-yl]-3-ethylurea (Reaction According to Scheme 6) 99.6 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.40 mmol), 73.6 mg of cyclohexylvinylboronic acid (0.48 mmol), 84.4 mg of sodium carbonate (0.80 mmol) and 33.4 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.04 mmol) were initially charged in 6 ml of dimethylformamide/water (1:1) under nitrogen. The mixture was then heated to 90 C. for 6.5 h. Distilled water was then added to the reaction mixture and the resulting precipitate was filtered off with suction. The further purification was effected by column chromatography on silica gel (ethyl acetate/heptane eluent mixture). A light brown solid was obtained. m.p.: 202-204 C. (decomp.) ESI-MS: found m/z=326.0 (M+H+); calc. 325 amu 1H NMR (d6-DMSO): delta=1.10-1.40 (m, 8H), 1.65-1.90 (m, 5H), 2.28-2.38 (m, 1H), 3.25-3.35 (m, 2H), 6.69 (d, 1H), 7.15 (dd, 1H), 7.58 (d, 1H), 8.28 (d, 1H), 8.98 (s, 1H), 9.15 (s, 1H), 10.05 (s, 1H) ppm. | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 68% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 6h;Inert atmosphere; | In a dried and purged vessel were added N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5- yl)-1-phenylmethanimine (0.2 g, 0.536 mmol, 1 eq.), <strong>[57002-01-4][(E)-2-cyclohexylvinyl]boronic acid</strong> (0.090 g, 0.58 mmol, 1.1 eq.), Na2CO3 (0.119 g, 1.12 mmol, 2.1 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.027 mmol, 0.05 eq.). A mixture of solvent was added toluene/ethanol/water (4/1/1 ) was added and the vessel purged with argon and sealed. The reaction was heated to 9OºC for 6 hrs. After cooling, 10 ml of EtOAc were added and the solids were filtered through a "Celite" plug and washed with EtOAc. The organics were separated, dried over MgSO4 and concentrated. The residue was <n="88"/>purified by chromatography on silica gel to give N-({6-[(E)-2-cyclohexylvinyl]pyridin-2-yl}methoxy)-1-(1- methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.155 g, 68 % yield) as a colorless gum. HPLC/MS : m/z = 403 (M+H) ; logP(HCooH) = 5.05 | 
 [ 1338718-68-5 ]
                                                    
                                                    [ 1338718-68-5 ]
 [ 57002-01-4 ]
                                                    
                                                    [ 57002-01-4 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 68% | With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 130℃; for 0.75h;Inert atmosphere; | Example 281 5-amino-N-(5-(4-(aminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-cyclohexylethyl)thiazole-4-carboxamide 281 A mixture of tert-butyl 4-(5-(4-(butyloxycarbonylaminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-bromothiazol-5-ylcarbamate (0.203 g, 0.33 mmol), Na2CO3 (70 mg, 0.66 mmol) and <strong>[57002-01-4]trans-(2-cyclohexylvinyl)boronic acid</strong> (0.102 g, 0.66 mmol) in DME (1.5 mL) and water (0.5 mL) was degassed by gently bubbling nitrogen through the mixture for 15 min. [1,1'-Bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (27 mg, 0.033 mmol) was then added and the mixture degassed for a further 10 min before being heated in a microwave at 130 C. for 45 min. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were passed through a phase separator cartridge and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (0-100% EtOAc/isohexane) to afford (E)-tert-butyl 4-(5-(4-(butyloxycarbonylaminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2-cyclohexylvinyl)thiazol-5-ylcarbamate as a brown gum (0.144 g, 68%). | 
 [ 17084-13-8 ]
                                                    
                                                    [ 17084-13-8 ]
 [ 1192147-21-9 ]
                                                    
                                                    [ 1192147-21-9 ]
 [ 57002-01-4 ]
                                                    
                                                    [ 57002-01-4 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 90% | With palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere; | Step 1 : To an argon saturated mixture of <strong>[57002-01-4](E)-(2-cyclohexylvinyl)boronic acid</strong> (8) (2.74 g, 16.0 mmol), 6-bromopicolinaldehyde (9) (3.0 g, 16 mmol), Pd(OAc)2 (0.04 g, 0.18 mmol), K2C03 (2M in z-PrOH, 30 mmol) was added PPh3 (0.20 g, 0.76 mmol). The reaction mixture was stirred at 70 C for 20 hours under N2, concentrated under reduced pressure and partitioned between H20 (80 ml) and ethyl acetate (80 ml). Organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash chromatography (30% - 50% EtOAc - hexanes gradient) gave alkene (10) as a pale yellow oil. Yield (3.1 g, 90%); 1H NMR (400 MHz, DMSO-d6) delta 9.34 (s, 1H), 7.93 (t, J= 7.6 Hz, 1H), 7.71 (d, J= 8.4 Hz, 1H), 7.69 (d, J= 8.4 Hz, 1H), 7.86 (dd, J= 6.8, 16.0 Hz, 1H), 6.54 (d, J= 16 Hz, 1H), 2.26-2.16 (m, 1H), 1.84-1.58 (m, 5H), 1.36-1.10 (m, 5H). | 
| 90% | With palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere; | £6L ?(RI ?5) tE6 2 (9p-oswu ?ZRN oot) WIN RT (%o6? FE) PJaA MOJJa( ajUd U SU (01) auajj AU QuatpU1SauUxaJ-oyQ3 %oc-%oE) £qdU1OwwO1qo JSU £q uot-Uogun alnSSald paonpai iapun pawauaouoo UU tOStUNSflO1p(quU laAo paup SUM IaJ(UJ otUU1Q Qw os) arnaop(a UU (jw os) OtR uaaaq pauotpnUd puU alnSSaldpaonpai iapun papmuaouoo tN iapun Srnoq o IOJ D00L U 1fl3S SUM ainjxnu uOl3oUal aj Qowm 9L0 ? oo) Eq SUM (jounu OE ?R01d1 U? w) EQy ?Qoanu810 ? too) t(vo)Pd ?Qoww 91 ? oE) (6) ap(qapJUutJ-OotdOwOlq-9 ?Qoanu 091 ? tLi (5) ptcrn otuOlOqQi(utAp(-xajopi(o-j-() jo ainpctw PW1flJUS UO1U UU oi :1 dais(Rd ?m) 0IU9EI ?(Rd ?w) SdI-tSI ?(RI ?w) 9I9 ?(RI ?ZR 91=1 ?P) td9 ?(RI ?ZR 091 ?89=f ?PP) 98L ?(RI ?ZR T8=1 ?P) 69L ?(RI ?ZR T8=1 ?P) ILL ?(RI ?ZR 9L=f ?1) | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 2.58 g | With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium tert-butylate; In isopropyl alcohol; at 20℃; for 15h;Inert atmosphere; | (1) Isopropanol (60 mL) was added to PEPPSI-IPr catalyst (161 mg, 0.24 mmol) and tert-butoxy potassium (2.65 g, 23.6 mmol) under an argon atmosphere, and the mixture was stirred at room temperature for 15 min. To the reaction mixture were added <strong>[57002-01-4]trans-(2-cyclohexylvinyl)boronic acid</strong> (2.00 g, 13.0 mmol) and 4-bromo-2-fluoroaniline (2.24 g, 11.8 mmol) successively and the mixture was stirred at room temperature for 15 hr. Water was added thereto, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to afford 4-[(E)-2-cyclohexylethenyl]-2-fluoroaniline as a reddish brown oil (2.58 g). | 

 [ 57002-01-4 ]
                                                    
                                                    [ 57002-01-4 ]