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CAS No. : | 139756-02-8 | MDL No. : | MFCD02927682 |
Formula : | C8H14N4O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PZMXDLWWQHYXGY-UHFFFAOYSA-N |
M.W : | 182.22 | Pubchem ID : | 3338044 |
Synonyms : |
|
Chemical Name : | 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
95% | With triethylamine; In ethyl acetate; at 0 - 25℃; for 2h;Product distribution / selectivity; | Preparation Ia: l-methyl-3-n-propyl-4- (2-ethoxybenzamido) -pyrazole-5-carbox- amide (V)In a 250 mL three-neck bottle, (XI) (21.8 g, 0.10 mol) was dissolved in ethylacetate (200 mL) and triethylamine (32 ml, 0.23 mol) to prepare a solution in an ice bath. 2- ethoxybenzoyl chloride (17.0 mL, 0.11 mmol) was added to the solution below 5 0C, and the mixture was stirred at room temperature for 2 hours. Water (170 mL) and petroleum ether (100 mL) were added to stop the reaction, and the mixture was stirred for another 0.5 h. The solid was filtrated and poured into water (170 mL) and stirred for 0.5 h, filtrated and dried (70 0C, 12 h) to afford compound (V) as a white solid (32.0 g, yield 95 %) . m.p. 153 - 154 0C. The product was re- crystallized from ethyl acetate/petroleum ether. 1H NMR (CDCI3, 300 MHz) delta: 0.93 (3H, t) , 1.54 (3H, t) , 1.65 (2H, m) , 2.54 (2H, t), 4.06 (3H, s), 4.31 (2H, q) , 5.62 (IH, br s) , 7.05 (IH, d) , 7.13 (IH, t), 7.54 (IH, t) , 7.91 (IH, br s) , 8.27 (IH, dd) , 9.47 (IH, s) . |
87% | With triethylamine; In dichloromethane; at 0 - 25℃; for 2h;Product distribution / selectivity; | Preparation 1 : l-methyl-3-n-propyl-4- (2-ethoxybenzamido) -pyrazole-5-carbox- amide (V)In a 250 mL three-neck bottle, (XI) (20 g, 0.11 mol) was dissolved in dichloromethane (100 mL) and triethylamine (22.2 g, 0.22 mol) to prepare a solution in an ice bath. 2- ethoxybenzoyl chloride was added to the solution below 5 0C, and the mixture was stirred at room temperature for 2 hours. Water (40 mL) was added to stop the reaction, and the layers were separated. The organic phase was washed with brine (30 mL) and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, followed by concentration. The resulting residue was purified by re- crystallizing from ethyl acetate/petroleum ether to obtain (V) (31.5 g, yield 87 %) as a white solid, m.p. 153 - 154 0C. 1H NMR (CDCl3, 300 MHz) delta: 0.93 (3H, t), 1.54 (3H, t), 1.65 (2H, m) , 2.54 (2H, t) , 4.06 (3H, s) , 4.31 (2H, q) , 5.62 (IH, br s) , <n="19"/>7 . 05 ( IH, d) , 7 . 13 ( IH, t ) , 7 . 54 ( IH , t ) , 7 . 91 ( IH , br s ) , 8 . 27 ( IH , dd) , 9 . 47 ( IH, s ) . |
87% | With triethylamine; In dichloromethane; at 25℃;Cooling with ice; | To a 250 mL three-neck flask, were added the compound of formula (XI) (20 g, 0.11 mol), dichloromethane (100 mL) and triethylamine (22.2 g, 0.22 mol) to prepare a solution in an ice bath below 5 C., followed by the slow addition of <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong>. After the mixture was stirred at room temperature for 2 hours, water (40 mL) was added to quench the reaction, and the layers were separated. The organic phase was washed with brine (30 mL) and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, followed by concentration. The resulting residue was purified by re-crystallising with ethyl acetate/petroleum ether to obtain the compound of formula (V) (31.5 g, yield 87%) as a white solid. m.p. 153154 C.; 1H NMR (CDCl3, 300 MHz) delta: 0.93 (3H, t), 1.54 (3H, t), 1.65 (2H, m), 2.54 (2H, t), 4.06 (3H, s), 4.31 (2H, q), 5.62 (1H, br s), 7.05 (1H, d), 7.13 (1H, t), 7.54 (1H, t), 7.91 (1H, br s), 8.27 (1H, dd), 9.47 (1H, s). |
80% | With dmap; triethylamine; In dichloromethane; at 50℃; for 0.166667h;Microwave irradiation; | 1-methyl-3-propyl-4 - (2-ethoxy methyl amido) pyrazole-5-carboxamide preparation: heating the prepared 7.5mmol2-ethoxy formyl chloride dissolved in 15 mu L methylene chloride (that is, the concentration of 500mol/L), adding 2.25mmol4-dimethyl aminopyridine, 19mmol triethylamine, stirring slowly dripping 19mmol4-amino-1-methyl-3-n-propyl -1H-pyrazole-5-carboxamide, microwave heating 50 C reaction 10 minutes, after the reaction of methylene chloride is removed by reduced pressure distillation, a small amount of ethanol re-crystallization, drying after filtration, a kind of white obtained 1-methyl-3-propyl-4 - (2-ethoxy methyl amido) pyrazole-5-carboxamide, the yield is 80%; |
With triethylamine; In dichloromethane; at 20℃; for 1h; | 50 g of the compound II was added to the reaction flask, 400 ml of dichloromethane was added thereto, and the mixture was stirred at room temperature, and 2 equivalents of the acid-binding agent triethylamine was added thereto, and the compound I was added thereto, and the mixture was stirred at room temperature for 1 hour, and the dichloromethane was distilled off under reduced pressure, and 250 ml of ethanol was added thereto. 3 equivalents of sodium hydroxide, the temperature was raised to reflux reaction for 3 hours, the reaction was cooled to room temperature, about half of the solvent was distilled off under reduced pressure, 400 ml of purified water was added, and hydrochloric acid was added to adjust pH = 8-9, stirring was continued for 1 hour, suction filtration and drying were obtained. Product 80g, yield 93.3%, HPLC purity 99.72% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Synthesis of BJ Step 7. 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (1 eq) and <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong> (1.1 eq) were suspended in ethanol 5 ml and the mixture heated at 75 C for 2 hours after conformation of forming of imine by TLC. Added CuC12 (3 eq) and the reaction mixture heated at 75 C under 02 for 2 hours. Aftercompletion of the reaction, the ethanol was removed under vacuum. Then workup with ethyl acetate and water. Separate the organic layer and Water layer re-extracted with 2x25 ml ethyl acetate. The combined organic layers are washed with brine solution, concentrated under vacuum. The residue was purified by column chromatography on silica the desired product Bf as a brown solid; yield 88%. ‘H NMR (400 MHz, DMSO)6: 12.54 (s 1H) 8.61 (s, 1H), 8.37 (d J=8.8 Hz 1H), 7.39 (d, J8.8 Hz 1H), 4.13 (s, 3H),3.84 (s, 3H), 2.78(t J=7.4Hz 2H), 1.76(m 2H), 0.95(tJ= 7.4Hz 3H). MASS: ESI [M +H] . 344.13; Elemental anal. calcd. for C16H17N504 C, 55.97; H, 4.99; N, 20.40; 0,18.64; found C, 55.87; H, 5.03; N, 20.43; 0, 18.67. | |
85% | With dipotassium peroxodisulfate; In water; dimethyl sulfoxide; at 100℃;Sealed tube; Microwave irradiation; | General procedure: We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine; In dichloromethane; at 20℃; | To a solution of I-07a (6 g, 32.97 mmol) in DCM (100 mL) was added Et3N(6.6 g, 65.34 mmol), <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (R-04a, 6.ig, 32.97 mmol). The reaction mixture was stirred at r.t. overnight. The reaction mixture was washed quenched by adding water and extracted with DCM. The organic phase was collected, dried over Na2SO4 and concentrated under vacuo to give I-08a (10.85 g, 98% yield). ESI-MS (Mi-i): 331 calc. for C17H22N403:330.2. |
98% | With triethylamine; In dichloromethane; at 20℃; | Preparation of intermediate l-08a: 5-(2- Ethoxyphenylcarbonylaminocarbonyl)-1 -methyl-3-propyl-1 /-/-pyrazol-4-amine To a solution of l-07a (6 g, 32.97 mmol) in DCM (100 ml_) was added Et3N (6.6 g, 65.34 mmol), <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (R-04a, 6.1 g, 32.97 mmol). The reaction mixture was stirred at r.t. overnight. The reaction mixture was washed quenched by adding water and extracted with DCM. The organic phase was collected, dried over Na2SO4 and concentrated under vacuo to give l-08a (10.85 g, 98% yield). ESI-MS (M+1 ): 331 calc. for C17H22N4O3: 330.2. |
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