There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 5763-61-1
*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. : | 5763-61-1 |
Formula : | C9H13NO2 |
M.W : | 167.21 |
SMILES Code : | NCC1=CC=C(OC)C(OC)=C1 |
MDL No. : | MFCD00008116 |
InChI Key : | DIVNUTGTTIRPQA-UHFFFAOYSA-N |
Pubchem ID : | 79832 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501 |
Class: | 8 |
UN#: | 2735 |
Packing Group: | Ⅲ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.1 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.48 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.88 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.92 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.12 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.27 |
Solubility | 9.0 mg/ml ; 0.0538 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.85 |
Solubility | 23.7 mg/ml ; 0.142 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.69 |
Solubility | 0.341 mg/ml ; 0.00204 mol/l |
Class? Solubility class: Log S scale |
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) |
No |
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 |
-7.07 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 |
1.0 |
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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.22 |
* 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 |
---|---|---|
PREPARATION 151 4-Chloro-2,5-difluoro-N-(3,4-dimethoxybenzyl)benzamide (1.66 g) was obtained from <strong>[132794-07-1]4-chloro-2,5-difluorobenzoic acid</strong> (1.05 g) and veratrylamine (0.91 mL) in a in a manner similar to preparation 1. NMR (DMSO-d6, delta): 3.73 (3H, s), 3.74 (3H, s), 4.39 (2H, d, J=6 Hz), 6.81-6.97 (3H, m), 7.67 (1H, dd, J=6, 9 Hz), 7.79 (1H, dd, J=6, 9 Hz), 8.96 (1H, t, J=6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 23 Following the procedure of Example 1, the reaction of 3,4-dimethoxybenzylamine with 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)-thieno-[2,3-d]-pyrimidine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With acetic acid; at 80℃; for 3h; | General procedure: 3-Bromomaleic anhydride (1.0 equiv, 5.65 mmol, 1.0 g) wasdissolved in AcOH (20 mL). Methylamine hydrochloride(1.0 equiv, 5.65 mmol, 0.37 g) was then added, and thereaction was heated at 80 °C for 3 h. Solvent was removed invacuo, and the crude mixture was purified by columnchromatography over silica gel (EtOAc?hexane 0?30percent)using an ISCOTM purification system to afford 0.97 g of awhite solid (90percent yield). |
67% | Example XI Preparation of l-Aryl-3-aza-bicyclo[3.1.0]hexane hydrochlorides Using Reaction Scheme 17 A. Synthesis of 3-Bromo-l-(3.4-dimethoxybenzyl)maleimide A solution of <strong>[5926-51-2]bromomaleic anhydride</strong> (Aldrich, 20.0 g, 0.113 mole) in anhydrous tetrahydrofuran (100 mL) under nitrogen was treated dropwise with a solution of 3,4-dimethoxybenzylamine (20.0 g, 0.1196 mole) in anhydrous THF (40 mL) over 30 min, and the stirred mixture was then refluxed for 3 h and maintained at room temperature for 20 h. The mixture was concentrated in vacuo, suspended in acetic anhydride (135 mL), treated with anhydrous sodium acetate (6.15 g, 75 mmol), and heated to 5O0C with stirring under nitrogen for 4 h (solids dissolved after a few minutes). The mixture was concentrated in vacuo and dissolved in methylene chloride (300 mL). The solution was washed with saturated aqueous sodium bicarbonate (150 mL), then with water (150 mL), dried (Na2SO4), and concentrated in vacuo to a brown residue. This was dissolved in methylene chloride and passed through a column of silica gel (~400 mL EPO <DP n="124"/>volume) and eluted with methylene chloride to afford a tan solid, which was recrystallized from ethyl acetate/heptane (2 crops) to afford 3-bromo-l-(3,4- dimethoxybenzyl)maleimide (24.75 g, 67percent) as a pale tan solid. NO MS (M+l) peak. 1H NMR (CDCl3) delta 6.89-6.94 (m, 2H), 6.84 (s, IH), 6.78 (d, IH, J=8Hz), 4.63 (s, 2H), 3.86 (s, 3H), 3.84 (s, 3H). | |
67% | Example XII Preparation of l-(4-Trifluoromethoxyphenyl)-3-azabicvclo[3.1 ,0]hexane, hydrochlorideUsinfi Reaction Scheme 17A. Synthesis of 3-Bromo-l-(3,4-dimethoxybenzyl)maIeimide EPO <DP n="104"/>A solution of <strong>[5926-51-2]bromomaleic anhydride</strong> (Aldrich, 20.0 g, 0.113 mole) in anhydrous tetrahydrofuran (100 mL) under nitrogen was treated dropwise with a solution of 3,4-dimethoxybenzylamine (20.0 g, 0.1196 mole) in anhydrous THF (40 mL) over 30 min, then the stirred mixture was refluxed for 3 h and maintained at room temperature for 20 h. The mixture was concentrated in vacuo, suspended in acetic anhydride (135 mL), treated with anhydrous sodium acetate (6.15 g, 75 mmol), and heated to 5O0C with stirring under nitrogen for 4 h (solids dissolved after a few minutes). The mixture was concentrated in vacuo and dissolved in methylene chloride (300 mL). The solution was washed with saturated aqueous sodium bicarbonate (150 mL), then with water (150 mL), dried (Na2SO4), and concentrated in vacuo to a brown residue. This was dissolved in methylene chloride and passed through a column of silica gel (-400 mL volume) and eluted with methylene chloride to afford a tan solid, which was recrystallized from ethyl acetate/heptane (2 crops) to afford 3-bromo-l-(3,4-dimethoxybenzyl)maleimide (24.75 g, 67percent) as a pale tan solid. NO MS (M+l) peak. 1H NMR (CDCl3) delta 6.89-6.94 (m, 2H), 6.84 (s, IH), 6.78 (d, IH, J=8Hz), 4.63 (s, 2H), 3.86 (s, 3H), 3.84 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In 1-methyl-pyrrolidin-2-one; at 100℃; for 16h; | (3,4-Dimethyloxy-benzyl)-(3-pyridin-4-yl-[2,6]naphthyridin-1-yl)-amine; <n="42"/>To a solution of 1-chloro-3-pyridin-4-yl-[2,6]naphthyridine (446.6 mg, 1.84 mmol) in 1-Methyl- pyrrolidin-2-one (8 ml_) is added 3,4-Dimethoxy-benzylamine (0.835 ml_, 5.54 mmol). The reaction mixture is heated to 1000C for 16 h, cooled to rt, the insoluble impurities are filtered and the filtrate concentrated under vacuum. Methanol is added and the formed precipitated filtered and dried under vacuum to yield to the title compound as a yellow solid (597 mg, 1.6 mmol, 87%), which is used without further purification for the next step. MS: 373.1 [M+1]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 31 To a solution of <strong>[154012-15-4]ethyl 4,6-dichloro-5-nitronicotinate</strong> (500 mg) in NMP (1 mL) were added DIPEA (0.328 mL) and a racemic mixture of (3R,4R)-1-benzyl-4-methylpiperidine-3-amine and (3S,4S)-1-benzyl-4-methylpiperidine-3-amine (385 mg). The reaction mixture was stirred at ambient temperature for 1 hour. To the reaction mixture were added DIPEA (0.328 mL) and 1-(3,4-dimethoxyphenyl)methaneamine (315 mg). The reaction mixture was stirred at 110C for 2 hours. The mixture was extracted with EtOAc and washed with water. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (EtOAc:n-hexane = 1:2) to afford a mixture (670 mg) of ethyl 4-[(3R,4R)-1-benzyl-4-methylpiperidine-3-yl]-amino}-6-[(3,4-dimethoxybenzyl)amino]-5-nitronicotinate and ethyl 4-[(3S,4S)-1-benzyl-4-methylpiperidine-3-yl]amino}-6-[(3,4-dimethoxybenzyl)amino]-5-nitroniootinate as a yellow amorphous solid. | ||
Preparation Example 16 To a mixed liquid of <strong>[154012-15-4]4,6-dichloro-5-nitronicotinic acid ethyl ester</strong> (5.7 g) in DMF (40 mL) were added rac-(3R,4R)-1-benzyl-4-methylpiperidin-3-amine (4.39 g) and N,N-diisopropylethylamine (3.7 mL), followed by stirring at room temperature for 1 hour. To the reaction mixture were added 1-(3,4-dimethoxyphenyl)methaneamine (4.8 mL) and N,N-diisopropylethylamine (9.4 mL), followed by stirring at 110 C. for 2 hours. The reaction mixture was quenched with water, and then the mixture was extracted with EtOAc and washed with water. The organic layer was dried over MgSO4 and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/Hx=1/4 to 1/2) to obtain ethyl rac-4-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]amino}-6-[(3,4-dimethoxybenzyl)amino]-5-nitronicotinate (9.9 g) as a yellow amorphous substance. | ||
Preparation Example 16; To a mixed liquid of <strong>[154012-15-4]4,6-dichloro-5-nitronicotinic acid ethyl ester</strong> (5.7 g) in DMF (40 mL) were added rac-(3R,4R)-1-benzyl-4-methylpiperidin-3-amine (4.39 g) and N,N-diisopropylethylamine (3.7 mL), followed by stirring at room temperature for 1 hour. To the reaction mixture were added 1-(3,4-dimethoxyphenyl)methaneamine (4.8 mL) and N,N-diisopropylethylamine (9.4 mL), followed by stirring at 110C for 2 hours. The reaction mixture was quenched with water, and then the mixture was extracted with EtOAc and washed with water. The organic layer was dried over MgSO4 and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/Hx = 1/4 to 1/2) to obtain ethyl rac-4-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]amino}-6-[(3,4-dimethoxybenzyl)amino]-5-nitronicotinate (9.9 g) as a yellow amorphous substance. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | General procedure: The round-bottom flask was charged with trans-Indole-3-acrylic acid (1.0 equiv.) or 3-Indolepropionic acid (1.0 equiv.) and the resulting mixture of DMF in CH2Cl2 (v:v, 1:3). DIPEA (1.5 equiv.) followed by HBTU (1.5 equiv.) were added to the solution. After stirring at room temperature for 30 min, amine (1.0 equiv.) was added and stirred overnight at RT. The excess solvent was evaporated and then diluted with water and EtOAc, and the two layers were separated. The aqueous solution was extracted with EtOAc. The combined organic solution was washed with water and brine, dried over magnesium sulfate, and filtered. The residue was purified by column chromatography on silica gel using 0-60% EtOAc in Hexanes as eluant to give the desired products 2a-2f. | |
68% | General procedure: To a solution of the acid derivative (1mmol) in CH2Cl2 were added triethylamine (2mmol) and ethyl chloroformate (1mmol), followed by stirring at 0C for 30min. After addition of the appropriate amine derivative (1.2mmol), the mixture was stirred for an additional 1h at 0C. Then, the reaction mixture was warmed to room temperature and stirred overnight. After the solvent was evaporated under reduced pressure, acetone was added, filtered, and evaporated. The residue was dissolved in CH2Cl2, and the organic phase was washed with a 1% NaHCO3 solution and brine, dried over Na2SO4, and evaporated under vacuum. The final residue was purified by flash column chromatography (Combiflash Rf) using CH2Cl2-MeOH (0-5%) as eluents. 4.3.11 (E)-N-(3,4-Dimethoxybenzyl)-3-(1H-indol-3-yl)acrylamide 3k 47 Yield 68%, mp 176-178 C; IR (FTIR/FTNIR-ATR): 1657 cm-1 (C=O), 3292 cm-1 (N-H). 1H NMR (DMSO-d6) delta: 11.52 (1H, s), 8.24 (1H, t, J = 5.6 Hz), 7.86 (1H, d, J = 7.6 Hz), 7.72 (1H, s), 7.61 (1H, d, J = 16 Hz), 7.42 (1H, d, J = 7.6 Hz), 7.13 (2H, m), 6.89 (2H, m), 6.80 (1H, m), 6.64 (1H, d, J = 16 Hz), 4.30 (2H, d, J = 5.2 Hz), 3.71 (3H, s), 3.69 (3H, s). 13C NMR (DMSO-d6) delta: 166.8, 149.2, 148.4, 138.0, 133.9, 132.7, 131.0, 125.5, 122.8, 120.9, 120.6, 120.2, 116.8, 112.9, 112.7, 112.3, 112.1, 56.2, 56.0, 42.8; HRMS C20H21N2O3 [M+H]+ Calcd 337.1552, Found m/z 337.1544. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 90℃; for 1.5h; | To a solution of (3 ,4-dimethoxyphenyl)methanamine (212 g, 1.27 mol) in anhydrous ethanol (1.1 L) was added dropwise the solution of crude 11 (300 g, assay 55% 1.15 mol) in anhydrous ethanol (1.1 L) over 30 mm using an addition funnel at 90 C (note: slow addition is crucial to good yield). The reaction was subsequently aged at 90 C for 1 h. After the reaction was complete shown by LCMS, the reaction was cooled to ambient temperature and concentrated. The crude residual was purified by trituation with methanol (5 V) to give methyl5 4-((3 ,4-dimethoxybenzyl)amino)-2,5-dihydrofuran-3 -carboxylate (14) as a solid. ?H NMR (CDC13, 400 MHz) : 7.08 (m, 1H), 6.46 (m, 2H), 4.76 (m, 4H), 4.19 (m, 2H), 3.81 (s, 3H), 3.81 (s, 3H), 3.69 (s, 3H), 2.69 (t, 1H). LC/MS (m/z): 294 (M+H). | |
In ethanol; at 90℃; for 1.5h; | Step B. Methyl 4- ( (3, 4-dimethoxybenzyl) amino) -2, 5-dihydrofuran-3-carboxylate (12)[0227][0228]To a solutio n of (3, 4-dimethoxyphenyl) methanamine (212 g, 1.27 mol) in anhydrous ethanol (1.1 L) was added dropwise the solution of crude 11 (300 g, assay 55 1.15 mol) in anhydrous ethanol (1.1 L) over 30 min using an addition funnel at 90 (note: slow addition is crucial to good yield) . The reaction was subsequently aged at 90 for 1 h. After the reaction was complete shown by LCMS, the reaction was cooled to ambient temperature and concentrated. The crude residual was purified by trituation with methanol (5 V) to give methyl 4- ( (3, 4-dimethoxybenzyl) amino) -2, 5-dihydrofuran-3-carboxylate (12) as a solid.1H NMR (CDCl3, 400 MHz) delta: 7.08 (m, 1H) , 6.46 (m, 2H) , 4.76 (m, 4H) , 4.19 (m, 2H) , 3.81 (s, 3H) , 3.81 (s, 3H) , 3.69 (s, 3H) , 2.69 (t, 1H) . LC/MS (m/z) : 294 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With triethylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 0.333333h;Inert atmosphere; Microwave irradiation; | To a solution of <strong>[205444-22-0]2-chloro-4-iodo-6-(trifluoromethyl)pyridine</strong> (1.0 g, 3.26 mmol) in NMP (5 mL) was added (3,4-dimethoxyphenyl)methanamine (2.45 mL, 16.29 mmol) and Et3N (2.26 mL, 16.29 mmol). The mixture was heated in a microwave at 100oC for 20 min. The reaction mixture was diluted with EA, washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (eluted with PE:EA = 15:1 to 10:1) to give the N-(3,4-dimethoxybenzyl) -4- iodo-6-(trifluoromethyl)pyridin-2-amine(400 mg, 28% yield) as a white solid. Retention time (LC-MS): 1.923 min. MH+ 439. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | The solution of 3,4-dimethoxybenzylamine (248 mu, 0.276 g, 1.65 mmol) in ethanol (4 mL) was added 37percent formaldehyde (62 mu, 0.049 g, 1.65 mmol). The mixture was stirred for 1 hour. Then the solution of <strong>[1198-14-7]5-bromoquinolin-8-ol</strong> (0.336 g, 1.5 mmol) in ethanol (5 mL) was added to the reaction mixture. After that the mixture was refluxed at 50°C for 72 hours. The reaction mixture was allowed to cool down and the obtained precipitate was filtered off, washed with ethanol and crystallized from ethanol to give the titled compound (0.130 g, 21 percent) as green crystals. Mp. 133-136 °C. 1 H NMR (300 MHz, CDCIs): delta 3.87 (d, 8H), 4.1 1 (s, 2H), 6.80-6.91 (m, 3H), 7.50-7.52 (m, 1 H), 7.65 (s, 1 H), 8.41 (d, 1 H), 8.82 (s, 1 H). 13C NMR (75 MHz, CDCI3): delta 52.0, 55.8, 55.9, 109.2, 1 10.9, 11 1.7, 119.5, 120.9, 121.0, 122.4, 127.1 , 129.6, 131.5, 135.4, 139.3, 148.4, 148.9, 152.0, 152.1. LCMS RT= 3.91 min. ESI+ m/z: 403.5 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With tert.-butylhydroperoxide; caesium carbonate; In water; acetonitrile; for 4h;Reflux; | General procedure: To a solution of 4-methoxybenzyl amine (1.0 mmol) and cesium carbonate (1.0 mmol) in 3 mL of CH3CN was added a solution of 70% aqueous TBHP (3.0 mmol) and the mixture was refluxed for 4 h. The mixture was then dried to vacuum and extracted three times with ethyl acetate followed by washing with brine,and dried over anhydrous Na2SO4. Evaporation of the solvent under vacuum afforded the crude product, which was furthur purified by column chromatography using hexane/ethyl acetate mixture and then analyzed by spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |