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CAS No. : | 1100598-32-0 | MDL No. : | MFCD18452823 |
Formula : | C29H28N6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AHYMHWXQRWRBKT-UHFFFAOYSA-N |
M.W : | 492.57 | Pubchem ID : | 25171648 |
Synonyms : |
EMD 1214063;MSC2156119
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With formic acid; In water; at 110℃; for 2.0h; | Alternatively, 3-(1-{3-[5-(1-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6- oxo-1 ,6-dihydro-pyridazin-3-yl)-benzonitrile (free base) can be synthesized as de- scribed in PCT/EP2008/003473, example 43, as follows: To a suspension of 4.15 g (20 mmol) of 3-(6-oxo-1 ,6-dihydro-pyridazin-3-yl)- benzonitrile in 40 ml of 1-methyl-2-pyrrolidon 6.00 g (21 mmol) of 5-bromo-2-(3- chloromethyl-pheny.)-pyrimidine and 2.76 g (341 rnmol) of potassiumcarbonate are given. The reaction mixture is stirred at 80 C for 18 hours. Subsequently, the reaction mixture is given onto 200 ml water. The resulting precipitate of 3-{1-[3-(5- bromopyrimidin-2-yl)-benzyl]-6-oxo-1 ,6-dihydro-pyridazin-3-yl}-benzonitrile is sucked off, washed with water and dried in vacuo.To a solution of solution of 18.0 g (41.0 mmol) of 3-{1-[3-(5-bromopyrimidin-2-yl)- benzyl]-6-oxo-1 ,6-dihydro-pyridazin-3-yl}-benzonitrile in 85 ml DMF 11.8 g (47 mmol) of bis(pinacolato)diboron and 11.9 g (122 mmol) of potassium acetate are given. The reaction mixture is heated up to 80 C under nitrogen. After 15 minutes of stirring at this temperature 273 mg (1.22 mmol) of palladium(ll)-acetate are added and the reaction mixture is stirred for 2 hours at 800C under nitrogen. Subsequently, the reaction mix- ture is allowed to cool down to room temperature before the addition of water and di- chloromethane, filtration over diatomite/kieselguhr and separation of the organic phase. The organic phase is dried over sodium sulphate and concentrated yielding 3-(6-oxo-1- {3-[5-(4l4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]-benzyl}-1 ,6-dihydro- pyridazin-3-yl)-benzonitrile as grey solid, which can be used for subsequent reactions without purification.To a suspension of 5.33 g (10.9 mmol) of 3-(6-oxo-1-{3-[5-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]-benzyl}-1,6-dihydro-pyridazin-3-yl)-benzonitrile in 35 ml THF and 35 ml water 4.93 g (49.4 mmol) of sodiumperborate are given in portions under ice cooling before it is stirred at room temperature for 2 hours. The reaction mixture is mixed with 300 ml of dichloromethan and 100 ml of saturated ammonium- chloride solution. The organic phase is separated, dried over sodium sulphate and concentrated. The residue of 3-{1-[3-(5-hydroxy-pyrimidin-2-yl)-benzyl]-6-oxo-1 ,6- dihydro-pyridazin-3-yl}-benzonitrile is re-crystallized from methanol.To a suspension of 25 g (65.6 mmol) of 3-{1-[3-(5-hydroxy-pyrimidin-2-yl)-benzyl]- 6-OXO-1 ,6-dihydro-pyridazin-3-yl}-benzonitrile in 250 ml THF 15.6 g (68.8 mmol) of N- Boc-4-piperidine-methanol and 19.1 g (72.1 mmol) of triphenylphosphine are subsequently added. Then, 14.9 ml (72.1 mmol) of diisopropylazodicarboxylate are added dropwise under ice cooling. The resulting solution is stirred at room temperature for 2 hours. The reaction mixture is further mixed with 750 ml of 2-propanol and 13.1 ml of a 0.5 M solution of potassiumhydroxid in ethanol. The resulting precipitate of 4-(2-{3-[3- (3-cyano-phenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-phenyl}-pyrimidin-5-yloxymethyl)- piperidine-1 -carbonic acid tert.-butylester is sucked off, washed with diethylether and dried in vacuo.To a solution of 16.0 g (28.0 mmol) of 4-(2-{3-[3-(3-cyano-phenyl)-6-oxo-6H- pyridazin-1-ylmethyl]-phenyl}-pyrimidin-5-yloxymethyl)-piperidine-1 -carbonic acid tert.- butylester in 80 ml formic acid 6.60 ml of 35% aqueous formaldehyde solution are given. The reaction mixture is stirred at a temperature of 110 C for 2 hours before 300 ml water are added. The reaction mixture is concentrated in vacuo to a volume of 150 ml and is then extracted with 200 ml of dichloromethane. The organic phase is washed with sodiumbicarbonate solution, dried over sodium sulphate and concentrated. The residue of 3-(1-{3-[5-(1-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6-oxo-1 ,6- dihydro-pyridazin-3-yl)-benzonitrile is re-crystallized from 2-propanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Cooling with ice; | 3-(1-{3-[5-(1-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6-oxo-1 ,6- dihydro-pyridazin-3-yl)-benzonitrile (free base) can be synthesized as described in PCT/EP2008/003473, example 40, and PCT/EP2008/005508, example 3, as follows: To a suspension of 13.0 g (56.5 mmol) of 3-(5-hydroxy-pyrimidin-2-yl)-benzoic acid methylester and 13.4 g (62.1 mmol) of N-Boc-piperidinemethanol in 115 ml THF 17.7 g (67.8 mmol) of triphenyl-phosphine are given. The suspension is cooled down to 5 C. To the suspension kept at this temperature 13.3 ml (67.8 mmol) of diisopropylazodicar- boxylate are given dropwise under stirring within 45 minutes. The reaction mixture is stirred at roomtemperature for one hour. Subsequently, further 22.2 g (84.7 mmol) of triphenylphosphine and 16.6 ml (84.7 mmol) of diisopropylazodicarboxylate are added. The reaction mixture is stirred at room temperature for 18 hours and concentrated in vacuo. The resulting solid of 4-[2-(3-methoxycarbonyl-phenyl)-pyrimidin-5-yloxymethyl]- piperidine-1 -carbonic acid tert.-butylester is sucked off, washed with diethylether and subjected to chromatography (silica gel column and dichloromethan/methanol as elu- ent/mobile phase). To a suspension of 1.71 g (3.99 mmol) of 4-[2-(3-methoxycarbonyl-phenyl)- pyrimidin-5-yloxymethyl]-piperidine-1 -carbonic acid tert.-butylester in 20 ml THF 25 ml (25 mmol) of a 1 M solution of diisobutylaluminiumhydride in THF are given dropwise under nitrogen. The reaction mixture is stirred for one hour at room temperature and mixed with a saturated solution of sodium sulfate. The resulting precipitate is sucked off and washed with THF and hot 2-propanol. The filtrate is concentrated and re- crystallized from tert.-butylmethylether, resulting in {3-[5-(1-methyl-piperidin-4- ylmethoxy)-pyrimidin-2-yl]-phenyl}-methanol as beige crystals. To a solution of 313 mg (1.00 mmol) of {3-[5-(1-methyl-piperidin-4-ylmethoxy)- pyrimidin-2-yl]-phenyl}-methanol in 2 ml THF 264 mg (1.30 mmol) of 3-(6-oxo-1 ,6- dihydro-pyridazin-3-yl)-benzonitrile and 397 mg (1.5 mmol) triphenylphosphine are added subsequently. The reaction mixture is cooled in an ice bath and 294 mul (1.5 mmol) of diisopropylazodicarboxylate are added dropwise. The reaction mixture is stirred at room temperature for 18 hours and then concentrated. The residue is subjected to chromatography (silica gel column and dichloromethan/methanol as elu- ent/mobile phase). The product containing fractions are pooled, concentrated and the residue of 3-(1-{3-[5-(1-Methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6-oxo-1 ,6- dihydro-pyridazin-3-yl)-benzonitrile is decocted with tert.-butylmethylether, sucked off and dried in vacuo. | |
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;Cooling with ice; | 264 mg (1.30 mmol) of 3-(6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile and 397 mg (1.5 mmol) of triphenylphosphine are added successively to a solution of 313 mg (1.00 mmol) of {3-[5-(1-methylpiperidin-4-ylmethoxy)pyrimidin-2-yl]-phenyl}methanol in 2 ml of THF. The reaction mixture is cooled in an ice bath, and 294 mul (1.5 mmol) of diisopropyl azodicarboxylate are added dropwise with stirring. The reaction mixture is stirred at room temperature for 18 hours and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol. The product-containing fractions are combined, evaporated, the residue is digested with tert-butyl methyl ether, filtered off with suction and dried in vacuo: 3-(1-{3-[5-(1-methylpiperidin-4-ylmethoxy)-pyrimidin-2-yl]benzyl}-6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile as colourless crystals; m.p. 177 C.; ESI 493;1H-NMR (d6-DMSO): delta [ppm]=1.33 (m, 2H), 1.75 (m, 3H), 1.89 (m, 2H), 2.17 (s, 3H), 2.80 (m, 2H), 4.05 (d, J=6.1 Hz, 2H), 5.45 (s, 2H), 7.16 (d, J=10 Hz, 1H), 7.49 (m, 2H), 7.73 (t, J=7.8 Hz, 1H), 7.93 (d, J=7.8 Hz, 1H), 8.17 (d, J=10 Hz, 1H), 8.24 (m, 2H), 8.38 (m, 2H), 8.64 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In diethyl ether; isopropyl alcohol; at 50℃; | Example 1 :Production of 3-(1-{3-[5-(1-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6-oxo- 1 ,6-dihydro-pyridazin-3-yl)-benzonitrile hydrochloride anhydrate in its crystalline modification A1Method 1Approx. 200 mg of 3-(1-{3-[5-(1-Methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6- oxo-1 ,6-dihydro-pyridazin-3-yl)-benzonitrile (free base) were dispersed in 5 ml. warm 2- propanole. After addition of approx. 0,1 ml. etheric HCI solution (10%), a clear solution was formed, which was further agitated at 50 0C until crystallisation set in. Agitation was continued at room temperature until completion of the crystallisation process. The obtained crystals were filtered and washed with ether. 1H-NMR (de-DMSO): delta [ppm] = 1.60 (m, 2H), 2.00 (m, 2H)1 2.07 (m, 1 H), 2.75 (d, 3H), 2.97 (m, 2H), 3.45 (m, 2H), 4.10 (d, 2H), 5.45 (s, 2H), 7.16 (d, 1 H), 7.50 (bm, 2H), 7.73 (t, 1 H), 7.93 (m, 1H), 8.18 (d, 1 H), 8.25 (bm, 2H), 8.38 (m, 2H), 8.67 (s, 2H), 9.90 (bs, 1 H).Ion Chromatography: 6.4 wt% Cl (equivalent to molar acid:base ratio of 0.96) | |
With hydrogenchloride; In water; acetone; at 20℃; | ?A7? 2.233 ml of 1N hydrochloric acid are added to 1 g of ?A257? in 150 ml of acetone, giving a clear solution. The solution is filtered, stirred at room temperature for 16 h, and the precipitated product 3-(1-{3-[5-(1-methyl- piperidin-4-ylmethoxy)pyrimidin-2-yl]benzyl}-6-oxo-1,6- dihydropyridazin-3-yl)benzonitrile, hydrochloride mono- hydrate (?A7?) is separated off. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of 3-(1-{3-[5-(1-methylpiperidin-4-ylmethoxy)pyrimidin-2-yl]-benzyl}-6-oxo-1,6-dihydropyridazin-3-yl)benzoic acid ("C29?) 2 ml of conc. HCl are added to 1 mmol of 3-(1-{3-[5-(1-methylpiperidin-4-ylmethoxy)pyrimidin-2-yl]benzyl}-6-oxo-1,6-dihydropyridazin-3-yl)benzo-nitrile, and the mixture is heated to 100 C., during which a clear solution forms, and the mixture is stirred at 100 C. for 4 hours. The reaction mixture is cooled and adjusted to a pH of about 7 using 2 N NaOH and approximately 1 N HCl. THF and saturated NaCl solution are added to the suspension. The organic phase is separated off. A crystalline precipitate forms in the aqueous phase. This is filtered off with suction and washed with water and dried in vacuo. HPLC: 2.48 min (method A), ESI: 512 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 2: formic acid / water / 2 h / 110 °C | ||
Multi-step reaction with 2 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 2: formic acid / water / 2 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 19.75 h / 5 - 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C / Cooling with ice | ||
Multi-step reaction with 3 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 19.75 h / 5 - 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 19.75 h / 5 - 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C / Cooling with ice | ||
Multi-step reaction with 3 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 19.75 h / 5 - 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In water; acetone | 1 Approx. 511 mg of 3-(1-{3-[5-(1-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]- benzyl}-6-oxo-1,6-dihydro-pyridazin-3-yl)-benzonitrile were dispersed in 75 mL acetone, and approx. 1.12 mL of 1 N aqueous HCl solution were added. No clear solution was obtained. However, the remaining solid-state residue was removed by filtration to yield a clear solution afterwards. The resulting clear solution was then incubated overnight, whereupon crystals were obtained. The crystals were separated by filtration and dried for 1 h in a vacuum drying cabinet at 65 °C (purification option 1) or the crystals were separated by filtration, washed with acetone, and dried in a vacuum drying cabinet (purification option 2). | |
With hydrogenchloride In water; acetone | 1 [00108] Approx. 511 mg of 3-(l-{3-[5-(l-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6-oxo-l,6-dihydro-pyridazin-3-yl)-benzonitrile were dispersed in 75 mL acetone, and approx. 1.12 mL of 1 N aqueous HC1 solution were added. No clear solution was obtained. However, the remaining solid-state residue was removed by filtration to yield a clear solution afterwards. The resulting clear solution was then incubated overnight, whereupon crystals were obtained. The crystals were separated by filtration and dried for 1 h in a vacuum drying cabinet at 65 °C (purification option 1) or the crystals were separated by filtration, washed with acetone, and dried in a vacuum drying cabinet (purification option 2). | |
With hydrogenchloride In water; acetone | 1 [00108] Approx. 511 mg of 3-(l-{3-[5-(l-methyl-piperidin-4-ylmethoxy)-pyrimidin-2-yl]-benzyl}-6-oxo-l,6-dihydro-pyridazin-3-yl)-benzonitrile were dispersed in 75 mL acetone, and approx. 1.12 mL of 1 N aqueous HC1 solution were added. No clear solution was obtained. However, the remaining solid-state residue was removed by filtration to yield a clear solution afterwards. The resulting clear solution was then incubated overnight, whereupon crystals were obtained. The crystals were separated by filtration and dried for 1 h in a vacuum drying cabinet at 65 °C (purification option 1) or the crystals were separated by filtration, washed with acetone, and dried in a vacuum drying cabinet (purification option 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 2: anhydrous potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: sodium perborate; water monomer / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 5: formic acid / water monomer / 2 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: sodium perborate; water / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 5: formic acid / water / 2 h / 110 °C | ||
Multi-step reaction with 5 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 2: potassium acetate / N,N-dimethyl-formamide / 2.25 h / 80 °C / Inert atmosphere 3: sodium perborate / tetrahydrofuran; water / 2 h / 20 °C / Cooling with ice 4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 5: formic acid / water / 2 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 2: sodium perborate; water / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 4: formic acid / water / 2 h / 110 °C | ||
Multi-step reaction with 4 steps 1: potassium acetate / N,N-dimethyl-formamide / 2.25 h / 80 °C / Inert atmosphere 2: sodium perborate / tetrahydrofuran; water / 2 h / 20 °C / Cooling with ice 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 4: formic acid / water / 2 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium perborate; water / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 3: formic acid / water / 2 h / 110 °C | ||
Multi-step reaction with 3 steps 1: sodium perborate / tetrahydrofuran; water / 2 h / 20 °C / Cooling with ice 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 3: formic acid / water / 2 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.2% | With tetrabutylammonium bromide; potassium carbonate In acetonitrile for 12h; Reflux; | 17-19 Example 17 Preparation of compound represented by formula 1 Acetonitrile (700 ml) was added to the reaction vessel, and the compound represented by formula 7a (37.63 g, 0.1 mol), the compound represented by formula 8 (23.66 g, 0.12 mol), and potassium carbonate (34.55 g, 0.25 mol) were added under stirring.and tetrabutylammonium bromide (1.93g, 0.006mol), the reaction system was stirred and heated to reflux, and the reaction was stirred at reflux for 12h. After the reaction was completed, the temperature was cooled to room temperature, the reaction solution was concentrated under reduced pressure to dryness, and ethanol (360ml) was added. ), stir to dissolve, slowly add 1.5 mol/l hydrochloric acid aqueous solution dropwise, adjust the pH value to 1-2, cool down to 5-7 °C, stir and crystallize for 6 h, filter, and vacuum dry the solid at 45 °C for 6 h to obtain formula 1. The compound (44.42 g) was shown in a yield of 81.2% and a purity of 99.7% by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.4% | With tetrabutylammonium bromide; potassium carbonate In toluene for 12h; Reflux; | 20-21 Example 21 Preparation of compound represented by formula 1 Toluene (660ml) was added to the reaction vessel, and the compound represented by formula 7b (33.18g, 0.1mol), the compound represented by formula 8 (25.64g, 0.13mol), potassium carbonate (55.28g, 0.4mol), and potassium carbonate (55.28g, 0.4mol) were added under stirring.Tetrabutylammonium bromide (1.61g, 0.005mol), the reaction system was stirred and heated to reflux, and the reaction was stirred at reflux for 12h. After the reaction was completed, the temperature was cooled to room temperature, the reaction solution was concentrated under reduced pressure to dryness, and ethanol (360ml) was added. , stir to dissolve, slowly add 1.5mol/l hydrochloric acid aqueous solution dropwise, adjust the pH value to 12, cool down to 28°C and stir for crystallization for 8h, filter, and dry the solid in vacuum at 45°C for 5h to obtain the formula shown in formula 1 Compound (43.98 g), yield 80.4%, HPLC purity 99.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1.5 h / 70 °C / Inert atmosphere 1.2: 6 h / 100 °C / Inert atmosphere 2.1: azobisisobutyronitrile; NBS / ethyl acetate / 6 h / 40 - 70 °C 3.1: tetrabutylammonium bromide; potassium carbonate / acetonitrile / 12 h / Reflux | ||
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1.5 h / 70 °C / Inert atmosphere 1.2: 6 h / 100 °C / Inert atmosphere 2.1: N-chloro-succinimide; azobisisobutyronitrile / ethyl acetate / 8 h / 40 - 65 °C 3.1: tetrabutylammonium bromide; potassium carbonate / toluene / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1.5 h / 70 °C / Inert atmosphere 1.2: 6 h / 100 °C / Inert atmosphere 2.1: azobisisobutyronitrile; NBS / ethyl acetate / 6 h / 40 - 70 °C 3.1: tetrabutylammonium bromide; potassium carbonate / acetonitrile / 12 h / Reflux | ||
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1.5 h / 70 °C / Inert atmosphere 1.2: 6 h / 100 °C / Inert atmosphere 2.1: N-chloro-succinimide; azobisisobutyronitrile / ethyl acetate / 8 h / 40 - 65 °C 3.1: tetrabutylammonium bromide; potassium carbonate / toluene / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: azobisisobutyronitrile; NBS / ethyl acetate / 6 h / 40 - 70 °C 2: tetrabutylammonium bromide; potassium carbonate / acetonitrile / 12 h / Reflux |
Tags: 1100598-32-0 synthesis path| 1100598-32-0 SDS| 1100598-32-0 COA| 1100598-32-0 purity| 1100598-32-0 application| 1100598-32-0 NMR| 1100598-32-0 COA| 1100598-32-0 structure
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P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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