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CAS No. : | 6829-40-9 | MDL No. : | MFCD00130009 |
Formula : | C7H13NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 175.18 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P301+P310-P311 | UN#: | 2811 |
Hazard Statements: | H301+H311+H331 | Packing Group: | Ⅲ |
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 |
---|---|---|
87% | for 2 h; Reflux | In a 250 mL round bottom flask, to 4 g (18.90 mmol) of diethylaminomalonate hydrochloride 5 were added 9.43 mL (0.885 g mL−1) of triethylorthoacetate, and the reaction mixture was refluxed for 2 h (oil bath). In the meantime, the colourless solution became yellow-brown. At the end, the solution was concentrated in a rotary evaporator giving a light yellow oily product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With ammonia In methanol at 80℃; | Diethylaminomalonate Aminomalondiamide 2-Carbamido-3-hydroxypynazine To an aqueous solution of diethylaminomalonate (hydrochloride form) was added sodium hydrogenocarbonate (pH> 7). After extraction, the organic phase was evaporated under reduced pressure and treated with an ammoniacal solution of methanol at 80°C overnight to give aminomalondiamide quantitatively. This compound was used for next step without purification and dissolved in water. To that solution was added glyoxal sodium bisulfite hemihydrate, this reaction mixture was stirred at 90°C for 3h, and then made basic with 58percent NH4OH. Then, 30percent H2O2 was added dropwise with rapid stirring to the cold solution (0°C) [J. Med. Chem. 1983, 26, 283-86, J. Heterocyclic Chem. 1979, 16, 193]. The reaction mixture was <n="131"/>allowed to warm at room temperature and the desired 2-hydroxy-3- carboxamidopyrazine precipitated. The solid was collected (63percent yield) and part of it recrystallized. |
87% | With ammonium chloride In water at 100℃; for 2 h; | 17.5 g of 2-aminomalonate ethyl ester and 22 g of a 50percent ammonium chloride aqueous solution were weighed and heated under reflux at 100 °C for 2 hours. After the reaction was completed, the mixture was filtered, and dried by hot air at 60 degrees for 8 hours.Get white 10.2g2-aminomalonamide in a yield of 87percent. |
49% | With ammonia In methanol at 60℃; for 19 h; Inert atmosphere | To diethyl 2-aminomalonate [3] (8.16 g; 46.6 mmol) prepared above, 2 M ammonia in methanol (233 ml; 466 mmol) was added and heated at 60°C for 19 hours under an argon atmosphere. The reaction solvent was removed under reduced pressure to give crude 2-aminomalonamide as pale yellow powders. The yellow colored impurities were removed by solid-liquid extraction with methanol (100 ml) by use of a Soxhlet extractor at 90°C for 21 hours under an argon atmosphere. The nearly colorless residue in the extraction thimble was recrystallized from water to give colorless 2-aminomalonamide (2.65 g; 22.6 mmol; yield 49percent). 1H-NMR (400 MHz, DMSO-d6): δ 7.38 (2H, brs), 7.23 (2H, brs), 3.73. (1H, s), 2.13 (2H, s). 13C-NMR (100 MHz, DMSO-d6): δ 172.0 (2C), 58.2 (1C). melting point: 192°C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine In dichloromethane at 20℃; Cooling with ice | Ice bath,Amino malonic acid diethyl ester (17.5 g, 0.1 mol)And triethylamine (20 g, 0.2 mol)250 ml of dichloromethane,Di-tert-butyl dicarbonate (26 g, 0.12 mil) was added to a three-necked flask, gradually raised to room temperature and stirred at that temperature,TLC monitoring reaction ends. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with dichloromethane (200 ml of X). The resulting organic phase was dried over anhydrous magnesium sulfate,Concentrated to give diethyl 2-Boc-aminomalonic acid as a colorless oil27g (yield 98percent) |
95% | With triethylamine In dichloromethane | EXAMPLE 48 Diethyl 2-t-butoxycarbonylamino malonate A solution of diethyl 2-aminomalonate (5 g, 23.6 mmol) and (Boc)2O (5.65 g, 25.96 mmol) in CH2Cl2 (50 mL) was treated slowly with Et3N (2.43 g, 24 mmol) for 10 minutes. After stirring 3 h at room temperature, the reaction was washed twice with water, dried and concentrated to give 6.16 g (95percent) of the title compound. 1H-NMR (500 MHz, CDCl3) δ5.54 (d, J=7.3 Hz, 1H), 4.93 (d, J=7.8 Hz, 1H), 4.26 (m, 4H), 1.44 (s, 9H), 1.29 (t, J=6.9 Hz, 6H). |
3 g | With triethylamine In ethanol at 35℃; for 4 h; | Step 1 : 2-tert-butoxycarbonyl amino malonate, Diethyl aminomalonate (21.2g) and ethanol (80.0 ml) were added to a flask at room temperature, (t-Boc)2 ( 24 g) in ethanol (20.0 ml) was added dropwise to the mixture, then triethylamine (14 ml) was added. The reaction mixture was heated to and maintained at 35 °C for 4 hours. After the reaction was complete, the reaction mixture was concentrated, then ethyl acetate (60.0 ml) was added to the reaction mass, washed with water two times, then separated the ethyl acetate layer, concentrated to obtain 2 - tert-butyl ethyl malonate oxycarbonylamino as a pale yellow oil: 3.0 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With ammonia; In methanol; at 80℃; | Diethylaminomalonate Aminomalondiamide 2-Carbamido-3-hydroxypynazine To an aqueous solution of diethylaminomalonate (hydrochloride form) was added sodium hydrogenocarbonate (pH> 7). After extraction, the organic phase was evaporated under reduced pressure and treated with an ammoniacal solution of methanol at 80C overnight to give aminomalondiamide quantitatively. This compound was used for next step without purification and dissolved in water. To that solution was added glyoxal sodium bisulfite hemihydrate, this reaction mixture was stirred at 90C for 3h, and then made basic with 58% NH4OH. Then, 30% H2O2 was added dropwise with rapid stirring to the cold solution (0C) [J. Med. Chem. 1983, 26, 283-86, J. Heterocyclic Chem. 1979, 16, 193]. The reaction mixture was <n="131"/>allowed to warm at room temperature and the desired 2-hydroxy-3- carboxamidopyrazine precipitated. The solid was collected (63% yield) and part of it recrystallized. |
87% | With ammonium chloride; In water; at 100℃; for 2h; | 17.5 g of 2-aminomalonate ethyl ester and 22 g of a 50% ammonium chloride aqueous solution were weighed and heated under reflux at 100 C for 2 hours. After the reaction was completed, the mixture was filtered, and dried by hot air at 60 degrees for 8 hours.Get white 10.2g2-aminomalonamide in a yield of 87%. |
49% | With ammonia; In methanol; at 60℃; for 19h;Inert atmosphere;Product distribution / selectivity; | To diethyl 2-aminomalonate [3] (8.16 g; 46.6 mmol) prepared above, 2 M ammonia in methanol (233 ml; 466 mmol) was added and heated at 60C for 19 hours under an argon atmosphere. The reaction solvent was removed under reduced pressure to give crude 2-aminomalonamide as pale yellow powders. The yellow colored impurities were removed by solid-liquid extraction with methanol (100 ml) by use of a Soxhlet extractor at 90C for 21 hours under an argon atmosphere. The nearly colorless residue in the extraction thimble was recrystallized from water to give colorless 2-aminomalonamide (2.65 g; 22.6 mmol; yield 49%). 1H-NMR (400 MHz, DMSO-d6): delta 7.38 (2H, brs), 7.23 (2H, brs), 3.73. (1H, s), 2.13 (2H, s). 13C-NMR (100 MHz, DMSO-d6): delta 172.0 (2C), 58.2 (1C). melting point: 192C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With acetic acid Heating; | |
63% | With acetic acid Heating; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine; In dichloromethane; at 20℃;Cooling with ice; | Ice bath,Amino malonic acid diethyl ester (17.5 g, 0.1 mol)And triethylamine (20 g, 0.2 mol)250 ml of dichloromethane,Di-tert-butyl dicarbonate (26 g, 0.12 mil) was added to a three-necked flask, gradually raised to room temperature and stirred at that temperature,TLC monitoring reaction ends. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with dichloromethane (200 ml of X). The resulting organic phase was dried over anhydrous magnesium sulfate,Concentrated to give diethyl 2-Boc-aminomalonic acid as a colorless oil27g (yield 98%) |
6.16 g (95%) | With triethylamine; In dichloromethane; | EXAMPLE 48 Diethyl 2-t-butoxycarbonylamino malonate A solution of diethyl 2-aminomalonate (5 g, 23.6 mmol) and (Boc)2O (5.65 g, 25.96 mmol) in CH2Cl2 (50 mL) was treated slowly with Et3N (2.43 g, 24 mmol) for 10 minutes. After stirring 3 h at room temperature, the reaction was washed twice with water, dried and concentrated to give 6.16 g (95%) of the title compound. 1H-NMR (500 MHz, CDCl3) δ5.54 (d, J=7.3 Hz, 1H), 4.93 (d, J=7.8 Hz, 1H), 4.26 (m, 4H), 1.44 (s, 9H), 1.29 (t, J=6.9 Hz, 6H). |
3 g | With triethylamine; In ethanol; at 35℃; for 4h; | Step 1 : 2-tert-butoxycarbonyl amino malonate, Diethyl aminomalonate (21.2g) and ethanol (80.0 ml) were added to a flask at room temperature, (t-Boc)2 ( 24 g) in ethanol (20.0 ml) was added dropwise to the mixture, then triethylamine (14 ml) was added. The reaction mixture was heated to and maintained at 35 C for 4 hours. After the reaction was complete, the reaction mixture was concentrated, then ethyl acetate (60.0 ml) was added to the reaction mass, washed with water two times, then separated the ethyl acetate layer, concentrated to obtain 2 - tert-butyl ethyl malonate oxycarbonylamino as a pale yellow oil: 3.0 g. |
With triethylamine; In dichloromethane; at 20℃; | To a suspension of diethyl aminomalonate (50 g, 285 mmol) and trimethylamine (57.8 g, 571 mmol) in dichloromethane (800 ml_) was added a solution of di-tert-butyl dicarbonate (93 g, 428 mmol) in dichloromethane (300 ml_) and the solution was allowed to stir at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SC>4, filtered and concentrated to provide the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In diethyl ether for 0.166667h; ice-bath; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With acetic acid for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol; at 20℃; for 0.5h; | (1 as,5aR)-1,1,2-Trimethyl-1a,4,5,5a-tetrahydro-1H-4-aza-cyclopropa [a]- pentalene (Pyrrole template, Structure 1) a) To a solution of diethyl aminomalonate hydrochloride (1.17 g, 5.5 mmol) in abs. ethanol (20 mL), is added a 1 M solution of sodium in abs. ethanol (11 mL, 11 mmol). The mixture is stirred at rt for 15 min before (1S, 5R)-2-(1-chloro-(E)- ethylidene)-6,6-dimethyl-bicyclo[3.1.0]hexan-3-one (S. A. Popov, A. Yu. Denisov, Yu. V. Gatilov, I. Yu. Bagryanskaya and A. V. Tkachev, Tetrahedron Asymmetry 5 (1994), 479-489; S. A. Popov, A. V. Tkachev; Synthetic Commun. 31 (2001), 233- 243) (923 mg, 5.0 mmol) is added. Stirring is continued for 30 min, the mixture is diluted with water (75 mL) and extracted with DCM (100 mL). The organic extract is dried over MgS04 and evaporated to give crude (1aS,5aR)-1,1,2-trimethyl- 1 a,4,5,5a-tetrahydro-1 H-4-aza-cyclopropa[a]pentalene-3-carboxylic acid ethyl ester (1.10 g) as a yellow oil. An analytical sample is purified by prep. HPLC to furnish (laS,5aR)-1,1,2-trimethyl-la,4,5,5a-tetrahydro-lH-4-aza-cyclo- propa [a]pentalene-3-carboxylic acid ethyl ester as a pale yellow oil. LC-MS: tR = 1.03 min, [M+1] + = 234.11. ¹H NMR (CDC13): No. 8.41 (s br, 1H), 4.27 (q, J = 7.6 Hz, 2H), 2.81 (dd, J = 7.0, 17.0 Hz, 1 H), 2.49 (d, J = 17.0 Hz, 1 H), 2.29 (s, 3H), 1.86 (dd, J = 1.2,6.4 Hz, 1 H), 1.67-1.60 (m, 1 H), 1.34 (t, J = 7.6 Hz, 3H), 1.10 (s, 3H), 0.61 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 3 A molecular sieve In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 3 A molecular sieve In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 3 A molecular sieve In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 3 A molecular sieve In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 3 A molecular sieve In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 3 A molecular sieve In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-2,6-bis(naphthalen-2-yl)-4-oxo-3,5-dioxa-4λ5-phosphacyclohepta[2,1-a;3,4-a']dinapthalen-4-ol In dichloromethane at 25℃; Molecular sieve; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83 % ee | With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 25℃; for 36h; Molecular sieve; Overall yield = 84 %; Overall yield = 45.3 mg; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83 % ee | With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 25℃; for 36h; Molecular sieve; Overall yield = 84 %; Overall yield = 45.3 mg; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; acetic acid at 100℃; for 23h; | 58.58a ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-2H- isoindole-1 -carboxylate A 25 mE roundbottom flask with stirbar was charged with 2-acetyl-5,5-dimethylcyclohexane-1 ,3-dione (5 g, 27.4 mmol) and sodium acetate (2.57 g, 31.3 mmol) in acetic acid (30 mE). The well-stirred mixture was placed in a 1000 C. oil bath and became homogeneous. A solution of diethyl 2-aminomalonate (4.184 g, 23.88 mmol) in 10 mE acetic acidwas added dropwise, andthe mixture was stirred at 1000 C. Afier 3 hours an additional portion of sodium acetate (2.75 g, 33.5 mmol) was added. Afier 20 hours, the mixture was poured over ice, then shaken in a separatory thnnel with water and ether (250 mE). The organics were washed twice with aqueous sodium bicarbonate then dried over anhydrous sodium sulfate. Filtration and solvent removal gave a brown solid. The crude material was adsorbed on silica gel and chromatographed on a 220 g silica gel cartridge eluting with 10-100% ethyl acetate/hexanes to provide the title compound. | |
With sodium acetate In acetic acid at 100℃; for 23h; | 58.58a ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-l-carboxylate Example 58a. ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-l-carboxylate. A 25 mL roundbottom flask with stirbar was charged with 2-acetyl-5,5-dimethylcyclohexane- 1,3-dione (5 g, 27.4 mmol) and sodium acetate (2.57 g, 31.3 mmol) in acetic acid (30 mL). The well-stirred mixture was placed in a 100 °C oil bath and became homogeneous. A solution of diethyl 2-aminomalonate (4.184 g, 23.88 mmol) in 10 mL acetic acid was added dropwise, and the mixture was stirred at 100 °C. After 3 hours an additional portion of sodium acetate (2.75 g, 33.5 mmol) was added. After 20 hours, the mixture was poured over ice, then shaken in a separatory funnel with water and ether (250 mL). The organics were washed twice with aqueous sodium bicarbonate then dried over anhydrous sodium sulfate. Filtration and solvent removal gave a brown solid. The crude material was adsorbed on silica gel and chromatographed on a 220 g silica gel cartridge eluting with 10-100% ethyl acetate/hexanes to provide the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium methylate In methanol at 20℃; for 48h; Reflux; | 1.1 Step 1: Preparation ofDimethyl3-amino-1H-pyrrole-2,4-dicarboxylate (27b) To a solution of diethyl aminomalonate (370.4 g, 1.75 mol) in methanol (3.6 L) atroom temperature was added a 5.4 M solution ofNaOMe (975 mL, 5.25 mol) in one portion (the reaction mixture was light brown in color). To the reaction mixture was addedethyl (ethoxymethylene)cyanoacetate (27a) (296 g, 1.75 mol) in three portions (not much temperature change was observed during the addition ~ 1 oc change, the reaction colorchanges from light brown to dark brown). The reaction mixture was heated at refluxed for48 h (TLC analysis 50% ethylacetate in hexane was done to check disappearance of starting material). The reaction mixture was neutralized by the addition of AcOH (210 mL,3.5 mole) to pH 6. The reaction mixture was concentrated in vacuo to furnish brownresidue. Residue was triturated with water (3 L), filtered, washed with water (500 mL) andhexanes. It was air-dried for 48 h and in vacuo oven at 60 oc to furnish dimethyl 3-amino-1H-pyrrole-2,4-dicarboxylate (27b) 287 g (83 %) as a brown solid. It was used as such forthe next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: aminomalonic acid diethyl ester; 1-(4-methylbenzyl)-1H-indole-2,3-dione With 9-phenanthrenyl In 1,1,2,2-tetrachloroethane at 25℃; for 0.5h; Molecular sieve; Stage #2: 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one In 1,1,2,2-tetrachloroethane at 25℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80 % ee | Stage #1: aminomalonic acid diethyl ester; 1-(3-methylbenzyl)indoline-2,3-dione With 9-phenanthrenyl In chloroform at 25℃; for 0.5h; Molecular sieve; Stage #2: 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one In chloroform at 25℃; for 24h; Overall yield = 58 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: aminomalonic acid diethyl ester; 1-(3-methylbenzyl)indoline-2,3-dione With 9-phenanthrenyl In 1,1,2,2-tetrachloroethane at 25℃; for 0.5h; Molecular sieve; Stage #2: 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one In 1,1,2,2-tetrachloroethane at 25℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 % ee | With C34H24O9P2 In toluene at 25℃; for 48h; Molecular sieve; Overall yield = 54 %; Overall yield = 36.9 mg; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With C34H24O9P2 In toluene at 25℃; for 48h; Molecular sieve; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of the requisite aldehyde 3 (0.12 mmol), diethyl 2-aminomalonate(2; 17.5 mg, 0.1 mmol) and AcOH (0.17 mul, 0.03 mmol) intoluene (0.5 mL) was stirred at r.t. for 20 min. To this resultant mixturewas added the appropriate unsaturated pyrazolone 1 (0.12mmol) and an additional 0.5 mL of toluene. The reaction mixture wasstirred at r.t. for 12 h. The resultant solution was evaporated underthe reduced pressure and the residue was purified by flash columnchromatography on silica gel (eluent: PE-EtOAc, 15:1 ? 5:1) to affordthe respective pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of the requisite aldehyde 3 (0.12 mmol), diethyl 2-aminomalonate(2; 17.5 mg, 0.1 mmol) and AcOH (0.17 mul, 0.03 mmol) intoluene (0.5 mL) was stirred at r.t. for 20 min. To this resultant mixturewas added the appropriate unsaturated pyrazolone 1 (0.12mmol) and an additional 0.5 mL of toluene. The reaction mixture wasstirred at r.t. for 12 h. The resultant solution was evaporated underthe reduced pressure and the residue was purified by flash columnchromatography on silica gel (eluent: PE-EtOAc, 15:1 ? 5:1) to affordthe respective pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of the requisite aldehyde 3 (0.12 mmol), diethyl 2-aminomalonate(2; 17.5 mg, 0.1 mmol) and AcOH (0.17 mul, 0.03 mmol) intoluene (0.5 mL) was stirred at r.t. for 20 min. To this resultant mixturewas added the appropriate unsaturated pyrazolone 1 (0.12mmol) and an additional 0.5 mL of toluene. The reaction mixture wasstirred at r.t. for 12 h. The resultant solution was evaporated underthe reduced pressure and the residue was purified by flash columnchromatography on silica gel (eluent: PE-EtOAc, 15:1 ? 5:1) to affordthe respective pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of the requisite aldehyde 3 (0.12 mmol), diethyl 2-aminomalonate(2; 17.5 mg, 0.1 mmol) and AcOH (0.17 mul, 0.03 mmol) intoluene (0.5 mL) was stirred at r.t. for 20 min. To this resultant mixturewas added the appropriate unsaturated pyrazolone 1 (0.12mmol) and an additional 0.5 mL of toluene. The reaction mixture wasstirred at r.t. for 12 h. The resultant solution was evaporated underthe reduced pressure and the residue was purified by flash columnchromatography on silica gel (eluent: PE-EtOAc, 15:1 ? 5:1) to affordthe respective pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of the requisite aldehyde 3 (0.12 mmol), diethyl 2-aminomalonate(2; 17.5 mg, 0.1 mmol) and AcOH (0.17 mul, 0.03 mmol) intoluene (0.5 mL) was stirred at r.t. for 20 min. To this resultant mixturewas added the appropriate unsaturated pyrazolone 1 (0.12mmol) and an additional 0.5 mL of toluene. The reaction mixture wasstirred at r.t. for 12 h. The resultant solution was evaporated underthe reduced pressure and the residue was purified by flash columnchromatography on silica gel (eluent: PE-EtOAc, 15:1 ? 5:1) to affordthe respective pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72 % ee | Stage #1: N,7-dimethylindoline-2,3-dione; aminomalonic acid diethyl ester With C48H37O4P In toluene at 25℃; for 0.5h; Molecular sieve; Stage #2: (3-methyl-1H-indol-2-yl)(phenyl)methanol In toluene at 50℃; for 12h; Molecular sieve; Overall yield = 60 %; Overall yield = 33.1 mg; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / diethyl ether / 16 h / 20 °C / Inert atmosphere; Sealed tube 2: (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; cesium acetate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone / tetrahydrofuran / 12 h / 20 °C / Schlenk technique; Molecular sieve; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium sulfate In diethyl ether at 20℃; for 16h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / diethyl ether / 16 h / 20 °C / Inert atmosphere; Sealed tube 2: (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; cesium acetate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone / tetrahydrofuran / 12 h / 20 °C / Schlenk technique; Molecular sieve; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium sulfate In diethyl ether at 20℃; for 16h; Inert atmosphere; Sealed tube; |
Tags: 6829-40-9 synthesis path| 6829-40-9 SDS| 6829-40-9 COA| 6829-40-9 purity| 6829-40-9 application| 6829-40-9 NMR| 6829-40-9 COA| 6829-40-9 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
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P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
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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