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CAS No. : | 14496-33-4 | MDL No. : | MFCD00069030 |
Formula : | C7H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CBVNYJPAGHUWKC-UHFFFAOYSA-N |
M.W : | 125.17 | Pubchem ID : | 57507 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
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With chloroform at 55℃; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium hydroxide; diethyl ether; ethylamine |
Yield | Reaction Conditions | Operation in experiment |
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With diethyl ether Erwaermen des Reaktionsprodukts mit Aluminiumisopropylat in Isopropylalkohol; |
Yield | Reaction Conditions | Operation in experiment |
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With 2-bromomethylfuran; potassium hydroxide; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
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With lithium aluminium tetrahydride |
Yield | Reaction Conditions | Operation in experiment |
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With ethanol; nickel Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
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With ethanol; platinum Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
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1: 50% 2: 32% | With hydrogen at 230℃; |
Yield | Reaction Conditions | Operation in experiment |
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With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
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With ethanol; sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 50% 2: 32% | With hydrogen at 230℃; other catalysts; other temperature; other pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 2: 85 percent / sodium acetate / aq. ethanol / 1.) 15 min, 2.) heating, 15 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50 percent / triethylamine / CH2Cl2 2: 75 percent / sodium acetate / aq. ethanol / 1.) 15 min, 2.) heating, 15 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 50 percent / triethylamine / CH2Cl2 2: 75 percent / sodium acetate / aq. ethanol / 1.) 15 min, 2.) heating, 15 min 3: 40 percent / lead tetraacetate / acetonitrile / -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 2: 85 percent / sodium acetate / aq. ethanol / 1.) 15 min, 2.) heating, 15 min 3: 40 percent / lead tetraacetate / acetonitrile / -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane | 5 Preparation of N-Ethyl-N-furfuryl-2-[2-nitro-5-(4-fluorophenoxy)phenoxy]propionamide EXAMPLE 5 Preparation of N-Ethyl-N-furfuryl-2-[2-nitro-5-(4-fluorophenoxy)phenoxy]propionamide N-Ethyl-N-furfurylamine (0.015 mole) triethylamine (5 ml) and methylene chloride (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The reaction mixture is cooled to about -15° C. and a solution of 2-[2-nitro-5-(4-fluorophenoxy)phenoxy]propionyl chloride (0.01 mole) in methylene chloride (50 ml) is added dropwise with stirring. After the addition is completed the reaction mixture is allowed to warm to room temperature with continued stirring. After this time the mixture is transferred to a separatory funnel and is washed with water and dilute aqueous sodium bicarbonate. The washed solution is then dried, filtered and stripped of solvent leaving a residue. This residue is then purified by subjecting it to elution chromatography using mixtures of ethyl acetate and hexane with increasing concentrations of ethyl acetate as the eluant. The desired fractions determined by IR spectroscopy are then stripped of solvent to yield the desired product N-ethyl-N-furfuryl-2-[2-nitro-5-(4-fluorophenoxy)phenoxy]propionamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 75℃; for 4h; Sealed tube; Combinatorial reaction / High throughput screening (HTS); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In ethanol at 180℃; for 3h; Microwave irradiation; | 62 Example 62: 7-(benzencsulfonyl)-4-N-ethyl-4-N-(furan-2-ylmethyl)- 5H-pyrrolo[3,2-djpyrinhidinc-4,6-diamine Example 5a: 7-(henzenesnhfonyl)-4-(2-methyhnorpholin-4-yl)-5H- pyrrolo[, 2-d]pyrimidin-6-amine To a stirred solution of 7-(benzenesulfonyl)-4-chloro-5H-pyrrolo[3,2-djpynmidin-6- amine (Intermediate 3; 200 mg, 648 pmol), 2-methylmorpholine (CM 27550-90-9; 262 mg, 2.59 mmol) and triethylamine (i8i iL, 1.30 mmol) in anhydrous DMF (8 mL) and the reaction mixture was heated under microwave irradiation at 130 °C for 2 b. The reaction mixture poured into water and extracted with EtOAc. The combined organic fractions were washed with brine and concentrated in vacuo. The crude product was purified by column chromatography (preparative HPLC, 5-40% acetonitrile / water (with o.i% ammonia)) to afford the title compound.ifl Example 62: 7-(benzencsulfonyl)-4-N-ethyl-4-N-(furan-2-ylmethyl)- 5H-pyrrolo[3,2-djpyrinhidinc-4,6-diamine Prepared as described for 7-(benzenesulfonyl)-4-(2-methylmorpholin-4-yI)-5H- pyrrolo[3,2-dlpyrimidin-6-amine (Example a) from 4-chloro-7-(phenylsulfonyl)-5H- pyrrolo[3,2-d]pyrimidin-6-amine (Intermediate 3; 200 mg, 648 pmol) and ethyl(furan2-ylmethyl)amine (CAS 14496-33-4; 324 mg, 2.59 mmofl in EtOH (8 mL) and the reaction mixture was heated under microwave irradiation at i8o °C for 3 h. The crude product was purified by column chromatography (C-i8 silica, -o% acetonitrfle / water (with o.i% ammonia)) to afford the tHe compound.‘H NMR (400 MHz, DMSO-d6) 6 ppm i.o6 (t, J=7 Hz, 3 H) 3.47 - 3.65 (m, 2 H) 4.79 (s, 2 H) 6.29 - 6.42 (m, 2 H) 6.42 - 6.54 (m, 2 H) 7.46 - 7.67 (m, 4 H) 8.04 (a, J=7 Hz, 2 II)8.13 (s, I H) 10.35 (in’. s., i H)MSES: 398 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 6 h / 60 °C 2: ammonium cerium (IV) nitrate / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 2 steps 1: methanol / 6 h / 60 °C / Inert atmosphere 2: copper dichloride; oxygen / 1,2-dichloro-ethane / 40 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 60℃; for 6h; | ||
In methanol at 60℃; for 6h; Inert atmosphere; | Pyrroles 2; General Procedure General procedure: A mixture of furfurylamine 7 (0.3 mmol), ynone 8 (0.3 mmol), and MeOH (15 mL) was stirred at 60 °C under an N2 atm, until the starting materials had disappeared (~6 h) (monitored by TLC). After the reaction mixture had been cooled to r.t., the MeOH was evaporated under reduced pressure, and CuCl2 (0.045 mmol, 15 mol%) and dry DCE (2 mL) were added to the residue under O2 (1 atm). The resulting mixture was stirred at 40 °C until the disappearance of 1 (~4 h), as indicated by TLC. H2O was then added, and the mixture was extractedwith CH2Cl2 (3 × 10 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (PE/EtOAc, 15:1) to give product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 60℃; for 6h; Inert atmosphere; | Pyrroles 2; General Procedure General procedure: A mixture of furfurylamine 7 (0.3 mmol), ynone 8 (0.3 mmol), and MeOH (15 mL) was stirred at 60 °C under an N2 atm, until the starting materials had disappeared (~6 h) (monitored by TLC). After the reaction mixture had been cooled to r.t., the MeOH was evaporated under reduced pressure, and CuCl2 (0.045 mmol, 15 mol%) and dry DCE (2 mL) were added to the residue under O2 (1 atm). The resulting mixture was stirred at 40 °C until the disappearance of 1 (~4 h), as indicated by TLC. H2O was then added, and the mixture was extractedwith CH2Cl2 (3 × 10 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (PE/EtOAc, 15:1) to give product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 6 h / 60 °C / Inert atmosphere 2: copper dichloride; oxygen / 1,2-dichloro-ethane / 40 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 60℃; for 6h; Inert atmosphere; | Pyrroles 2; General Procedure General procedure: A mixture of furfurylamine 7 (0.3 mmol), ynone 8 (0.3 mmol), and MeOH (15 mL) was stirred at 60 °C under an N2 atm, until the starting materials had disappeared (~6 h) (monitored by TLC). After the reaction mixture had been cooled to r.t., the MeOH was evaporated under reduced pressure, and CuCl2 (0.045 mmol, 15 mol%) and dry DCE (2 mL) were added to the residue under O2 (1 atm). The resulting mixture was stirred at 40 °C until the disappearance of 1 (~4 h), as indicated by TLC. H2O was then added, and the mixture was extractedwith CH2Cl2 (3 × 10 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (PE/EtOAc, 15:1) to give product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11 %Spectr. | With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In neat (no solvent) at 140℃; for 24h; Inert atmosphere; Sealed tube; | General procedure for hydroboration of secondary and tertiary amides General procedure: N,N-dimethylbenzamide (0.0746 g,0.5 mmol), or N-methylbenzamide (0.0676 g, 0.5 mmol) was taken in culture tube (11 ml) at 25 °C, sealed with septum, the air in culture tube was replaced with argon gas. After adding pinacolborane (0.36 ml, 2.5 mmol 5 equiv), the screw cap was closed, stirred at 120 °C for 24 h. Afterthis time, it was cooled to room temperature, excess HBpin was quenched by adding water (0.1 ml). After adding 2 ml of 5 N NaOH (aq), reaction mixture was extracted with ether (20 ml). The organic part was dried over MgSO4, filtered and dried under high vacuum to remove volatile organic impurities. The yield was analyzed by 1HNMR (using acetonitrile [8μl, 0.33 eq] as an internal standard). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 25 °C 2: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / neat (no solvent) / 24 h / 140 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.2% | Stage #1: ethyl(furan-2-ylmethyl)amine; carbon disulfide In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: With carbon tetrabromide In N,N-dimethyl-formamide at 20℃; for 0.5h; | 3.1. Chemical Synthesis of Compounds General procedure: CS2 (152 mg, 2.0 mmol) was added to a solution of 4 mmol of amine (3) in 4 mL ofDMF at 0 C. The mixture was stirred for 5 min, after which CBr4 (663 mg, 2 mmol) wasadded. The mixture was further stirred at room temperature (RT) for 30 min. The reactionwas poured into ice water (40 mL) and extracted with 2 40 mL CH2Cl2. The organiclayer was then dried over CaCl2 and concentrated under vacuum. Purification by columnchromatography on silica gel provided the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
432 mg | With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; 4-dimethylaminopyridine / dichloromethane / 3 h / 0 - 20 °C / Sealed tube 2: palladium (II) chloride; lithium chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 12 h / 20 °C / Schlenk technique; Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: furan-2-carbaldehyde; ethylamine With methanol at 20℃; for 12h; Sealed tube; Stage #2: With sodium tetrahydridoborate at 0 - 20℃; for 2h; Sealed tube; |
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