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CAS No. : | 105434-90-0 | MDL No. : | MFCD03468385 |
Formula : | C6H9N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CPQKGGOPHDHAMN-UHFFFAOYSA-N |
M.W : | 155.16 | Pubchem ID : | 4321844 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 39.08 |
TPSA : | 81.0 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.95 cm/s |
Log Po/w (iLOGP) : | 0.92 |
Log Po/w (XLOGP3) : | 0.42 |
Log Po/w (WLOGP) : | 0.18 |
Log Po/w (MLOGP) : | -0.18 |
Log Po/w (SILICOS-IT) : | 0.39 |
Consensus Log Po/w : | 0.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.2 |
Solubility : | 9.68 mg/ml ; 0.0624 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.69 |
Solubility : | 3.18 mg/ml ; 0.0205 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.34 |
Solubility : | 7.04 mg/ml ; 0.0454 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.0 |
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 |
---|---|---|
90% | With hydrogen In ethanol at 20℃; for 18 h; | To a solution of 5-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester (0.925 g, 0.500 mmol) in absolute ethanol (10 cm3) was added 10percent Pd/C (0.100 g). The mixture was stirred under an atmosphere of H2 at room temperature for 18 hours, filtered through Celite and the solvent removed under reduced pressure to give a green solid (0.70 g, 90percent). 1H (CD3OD): 6.0 (s, IH), 4.3 (q, 2H, J=7.1, CO2CH2CH3), 1.4 (t, 3H, J=7.1,CO2CH2CH3). m/z (ES+): 156 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 70℃; for 0.666667 h; Stage #2: With hydrogenchloride; hydrazinecarboxylic acid methyl ester In ethanol; water at 30℃; for 20 h; Cooling with ice Stage #3: With potassium carbonate In ethanol; water at 90℃; for 0.5 h; |
To a solution of diethyl oxalate (10.0 g, 68.4 mM) in THF (10 mL), there were added 18-crown-6 (1.80 mg, 6.84 mM) and potassium tert-butoxide (1M THF solution, 71.6 mL, 71.6 mM), then acetonitrile (3.99 mL, 75.2 mM) was further added to the mixture at 0° C. and the resulting mixture was stirred for 10 minutes. The temperature of this solution was raised up to 70° C. and it was stirred for 30 minutes at that temperature. The resulting suspension was filtered and the solid was washed with diethyl ether. The resulting solid was suspended in ethanol (100 mL), followed by the addition of water (20 mL), and then concentrated hydrochloric acid (3.0 mL) and methyl carbazinate (3.61 g, 39.7 mM) with ice-cooling and the stirring of the resulting mixture at room temperature for 20 hours. After the completion of the stirring operation, potassium carbonate (2.74 g, 19.8 mM) was added to this suspension and the latter was stirred at 90° C. for 30 minutes. This reaction liquid was concentrated under reduced pressure, the resulting concentrate was diluted with water and the mixture was extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate, the solvent was distilled off and then the resulting solid was sufficiently washed with diethyl ether to thus give the title compound (5.34 g, yield: 50percent). 1H-NMR (300 MHz, DMSO): δ 1.23 (t, 3H, J=6.9 Hz), 4.19 (q, 2H, J=6.9 Hz), 4.74-5.12 (br, 2H), 5.64-5.89 (br, 1H), 12.09-12.53 (br, 1H); MS (ESI) m/z 156 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.3% | Stage #1: With hydrogenchloride In ethanol; water at 20℃; for 0.25 h; Stage #2: at 20℃; Stage #3: With potassium carbonate In methanol; water at 60℃; for 4 h; Heating / reflux |
A 10 L three-necked flask is equipped with mechanical stirrer, reflux condenser and nitrogen inlet. To ethyl 3-cyano-2-oxopropionate sodium salt ("NaCOPE") (653.18 g; 4.0 mol), 585 mL of water, 3.6 L of ethanol and 350 mL of hydrochloric acid (12N; 4.2 mol) are added. The resulting suspension is stirred at RT for 15 min. Then, methyl hydrazino formiate (356.0 g; 3.95 mol) is added as a solid material. A slightly exothermic reaction occurs. After the mixture is stirred at RT for 6 h, another portion of methyl hydrazino formiate (12.0 g; 133.7 mmol) is added and the orange suspension is stirred at RT over night. Then potassium carbonate (K2CO3, 300.0 g; 2.17 mol) is added, followed by 250 mL of water. The internal temperature rises to 60° C. and a vigorous evolution of gas starts. The mixture is heated at reflux for four hours. After cooling to RT, the alcohol is evaporated to yield a red paste, which is taken up in 1 L of water and 3 L of ethyl acetate. The aqueous phase is extracted with another 500 mL portion of ethyl acetate. The organic extracts are washed with brine and dried over sodium sulfate (Na2SO4). After filtration the solvent is evaporated to yield 330 g of a brown paste. This crude product is mixed with 1 L of ether to give a light brown solid, which is separated from an orange liquid phase by filtration. The solid is dried under vacuum to yield 229.12 g (7). The liquid phase is evaporated; the residue is taken up in 250 mL of ether and cooled to -30° C. to yield another 15.09 g of 7. The total yield of 7 is 244.21 g (1.57 mol; 39.3percent). Physical characteristics are as follows: 1H-NMR (DMSO): δ (ppm) 1.26, 4.21, 5.0, 5.76, 12.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.3% | A 10 L three-necked flask is equipped with mechanical stirrer, reflux condenser and nitrogen inlet. To ethyl 3-cyano-2-oxopropionate sodium salt (?NaCOPE?) (653.18 g; 4.0 mol), 585 mL of water, 3.6 L of ethanol and 350 mL of hydrochloric acid (12N; 4.2 mol) are added. The resulting suspension is stirred at RT for 15 min. Then, methyl hydrazino formiate (356.0 g; 3.95 mol) is added as a solid material. A slightly exothermic reaction occurs. After the mixture is stirred at RT for 6 h, another portion of methyl hydrazino formiate (12.0 g; 133.7 mmol) is added and the orange suspension is stirred at RT over night. Then potassium carbonate (K2CO3, 300.0 g; 2.17 mol) is added, followed by 250 mL of water. The internal temperature rises to 60 C. and a vigorous evolution of gas starts. The mixture is heated at reflux for four hours. After cooling to RT, the alcohol is evaporated to yield a red paste, which is taken up in 1 L of water and 3 L of ethyl acetate. The aqueous phase is extracted with another 500 mL portion of ethyl acetate. The organic extracts are washed with brine and dried over sodium sulfate (Na2SO4). After filtration the solvent is evaporated to yield 330 g of a brown paste. This crude product is mixed with 1 L of ether to give a light brown solid, which is separated from an orange liquid phase by filtration. The solid is dried under vacuum to yield 229.12 g (7). The liquid phase is evaporated; the residue is taken up in 250 mL of ether and cooled to -30 C. to yield another 15.09 g of 7. The total yield of 7 is 244.21 g (1.57 mol; 39.3%). Physical characteristics are as follows: 1H-NMR (DMSO): delta (ppm) 1.26, 4.21, 5.0, 5.76, 12.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.8% | With hydrogenchloride; In ethanol; water; at 20℃; | A 2 L round bottom flask is charged with <strong>[105434-90-0]ethyl 5-aminopyrazole-3-carboxylate</strong> (7) (44.92 g; 289.50 mmol), 1.2 L of ethanol and 27 mL of hydrochloric acid (12N; 324.0 mmol). 2-Bromomalonaldehyde (43.71 g; 289.54 mmol) is added as a solid to the resulting yellow solution. A light brown solution is formed, from which a tan solid started to precipitate after 15 min. The suspension is stirred at RT over night and thereafter, filtered with suction. The solid is washed with 200 mL of ether to yield 62.50 g of (8a) after drying at 40 C./1 Torr. Additional crystals are isolated from the filtrate by concentration and cooling to -30 C. A total yield of 74.12 g (274.4 mmol; 94.8%) of 8a is obtained with a HPLC-purity>97%. Physical characteristics are: 1H-NMR (DMSO): delta (ppm) 1.35, 4.39, 7.24, 8.74, 9.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; at 20℃; for 2h; | (Step 4) Production of ethyl 5-(2-chloro-4,5-difluoro-benzoylamino)-1H-pyrazole-3-carboxylate To a solution of <strong>[105434-90-0]ethyl 5-amino-3-pyrazolecarboxylate</strong> (265.38 g) in tetrahydrofuran (1.33 L) was added pyridine (153 mL). To this solution, 2-chloro-4,5-difluoro-benzoyl chloride (362.00 g) produced in Step 1 of Reference Example 1 was added dropwise with ice cooling, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated and recrystallized with 2-propanol/water to obtain the title compound (538.85 g) as white crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; In 1,1-dichloroethane; at 170℃; for 0.333333h;Microwave irradiation; | A solution of S-Amino-lH-pyrazole-S-carboxylic acid ethyl ester (0.0775 g, 0.500 mmol), benzaldehyde (0.117 g, 1.10 mmol) and sodium triacetoxyborohydride (0.318 g, 1.50 mmol) in dichloroethane (2 cm3) was allowed to react at 17O0C for 1200 seconds utilizing Smith Synthesizer. The solution was diluted with further dichloroethane (10 cm3), washed with NaHCO3 until there was no further gas evolution, then with brine. The organic phase was dried over anhydrous Na2SO4, filtered, and solvent removed under reduced pressure to give a brown oil. The crude product was taken into acetom'trile (3 cm3) and purified by preparatory HPLC to give 5-dibenzylamino-lH-rhoyrazole-3-carboxylic acid ethyl ester.5-Dibenzylamino-lH-pyrazole-3-carboxylic acid ethyl ester was taken up in IM lithium hydroxide: tetrahydrofuran : methanol (1 : 5 : 1) (10 cm3) and heated at 650C for 18 hours. Solvent was removed under reduced pressure and the crude product was taken to a pH of 1 with 0.1M aqueous HCl and extracted with ethyl acetate (10 cm3). The organic phase was dried over anhydrous Na2SO4, filtered, and solvent removed under reduced pressure to give 5- (dibenzylammo)-lH-pyrazole-3-carboxylic acid as a brown, glassy solid. 1H (DMSO-d6): 7.35-7.2 (m, 1OH, (CH2C6Hs)2), 6.00 (s, IH, pyrazole-H), 4.5 (s, 4H, (CH2C6H5)2). m/z (ES+): 308 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; In 1,1-dichloroethane; at 60℃; | A solution of 5-Amino~lH-pyrazole-3~carboxylic acid ethyl ester (0.0775 g, 0.500 mmol), benzaldehyde (0.064 g, 0.60 mmol) and sodium triacetoxyborohydride (0.212 g, 1.00 mmol) in dichloroethane (5 cm3) and stirred over night at 6O0C. The solution was diluted with further dichloroethane (10 cm3), was washed with NaHCO3, until there was no further gas evolution, then with brine. The organic phase was dried over anhydrous Na2SO4, filtered, and solvent removed under reduced pressure to give a brown oil. The crude product was taken into acetonitrile (3 cm3) and purified by preparatory HPLC to give 5-benzylamino-lH-pyrazole-3- carboxylic acid ethyl ester.5-Benzylamino-lH-pyrazole-3-carboxylic acid ethyl ester was taken up in IM lithium hydroxide: tetrahydrofuran : methanol (1 : 5 : 1) (10 cm3)and heated at reflux over night. Solvent EPO <DP n="63"/>was removed under reduced pressure and the crude product was acidified to pH 1 with 0.1M HCl and extracted with ethyl acetate (10 cm3). The organic phase was dried over anhydrous Na2SO4, filtered, and solvent removed under reduced pressure to give a brown, glassy solid. 1H (DMSO- d6): 7.35-7.2 (m, 5H, CH2C6H5), 6.0 (s, IH), 4.5 (s, 2H, CH2C6H5). m/z (ES+): 218 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 18h; | To a solution of 5-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester (0.925 g, 0.500 mmol) in absolute ethanol (10 cm3) was added 10% Pd/C (0.100 g). The mixture was stirred under an atmosphere of H2 at room temperature for 18 hours, filtered through Celite and the solvent removed under reduced pressure to give a green solid (0.70 g, 90%). 1H (CD3OD): 6.0 (s, IH), 4.3 (q, 2H, J=7.1, CO2CH2CH3), 1.4 (t, 3H, J=7.1,CO2CH2CH3). m/z (ES+): 156 [M+H]+ |
53% | With acetic acid; zinc; In water; at 0 - 20℃; for 3h; | Zinc powder (50 g, 765 mmol) was added portion-wise at 0 C to a solution of ethyl 5-nitro-1H- pyrazole-3-carboxylate (10 g, 53.5 mmol) in acetic acid (100 mL) and water (20 mL). The resulting mixture was stirred to rt for 3 h, then filtered and the pH of the filtrate was adjusted to 8 with ammonium hydroxde and extracted with EtOAc (2 x 500 mL). The combined organic layers dried over Na2S04 and concentrated which gave the title compound (6 g, 53%) as a solid. The compound was used in next step without further purification. MS (ES+) 156.11 [M+H]+. |
palladium-carbon; In tetrahydrofuran; ethyl acetate; | Step 3: Preparation of Ethyl 5-amino-3-pyrazolecarboxylate To a solution of ethyl 5-nitro-3-pyrazolecarboxylate (331.48 g) in tetrahydrofuran (1.5 L) and ethyl acetate (1.5 L) was added 7.5% palladium-carbon (30.036 g), and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure and the residual solid was recrystallized from ethyl acetate-hexane to obtain the title compound (265.38 g) as white crystals. |
With hydrogen;palladium-carbon; In tetrahydrofuran; ethyl acetate; at 20℃; | (Step 3) Production of ethyl 5-amino-3-pyrazolecarboxylate To a solution of ethyl 5-nitro-3-pyrazolecarboxylate (331.48 g) in tetrahydrofuran (1.5 L) and ethyl acetate (1.5 L) was added 7.5% palladium carbon (30.036 g), and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. The catalyst was filtered off, the filtrate was concentrated, and the resulting solid was recrystallized with ethyl acetate/hexane to obtain the title compound (265.38 g) as white crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In methanol; for 2h;Heating / reflux; | Step A. 2-Amino-lH-pyrazole-3-carboxylic acid ethyl ester (0.7 g, 5 mmol) and methyl acetoacetate (0.62 g, 5 mmol) in methanol (10 mL) were heated to reflux for 2h and cooled down. The resulting precipitate was collected to give white solid 5-methyl-pyrazolo[l,5-a]pyrimidine-3,7-dicarboxylic acid 3-ethyl ester 7-methyl ester (0.8 g mg, yield, 60%). MS (M + H): 264. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; at 0 - 20℃; | Subsequently, to a solution of <strong>[105434-90-0]ethyl 5-amino-3-pyrazolecarboxylate</strong> (1.337 g) in tetrahydrofuran (15 mL) was added pyridine (1.385 mL), and then a solution of 4,5-difluoro-2-methyl-benzoyl chloride in tetrahydrofuran (2 mL) was added dropwise with ice cooling. After stirring overnight at room temperature, ethanol (5 mL) and water (45 mL) were added to the reaction mixture, and the precipitated solid was collected by filtration to obtain the title compound (2.271 g) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | (a) 5-Amino-2-butylpyrazol-3-carboxylic acid ethyl ester; Sodium hydride (920 mg, 21 mmol) was added to a solution of <strong>[105434-90-0]5-aminopyrazol-3-carboxylic acid ethyl ester</strong> (3.10 g, 20 mmol) in acetonitrile (100 mL) under a nitrogen atmosphere, and the obtained mixture was then stirred at room temperature for 30 minutes. The reaction solution was cooled on ice, and butyl iodide (2.3 mL, 20 mmol) was then added thereto. The obtained mixture was stirred at room temperature for 1 hour, and then at 60C for 1 hour. The reaction solution was left at room temperature overnight. Thereafter, the solvent was distilled away, and water was then added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated saline, and it was dried over sodium sulfate and was then concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain the title compound (1.60 g, yield: 38%) in the form of a pale yellow oily substance. 1H NMR (400 MHz, CDCl3): delta (ppm) = 7.58 (1H, s), 4.66 (2H, brs), 4.27 (2H, q, J = 7.1 Hz), 3.90 (2H, t, J = 7.1 Hz), 1.84-1.76 (2H, m), 1.37-1.24 (5H, m), 0.94 (3H, t, J = 7.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; diisopropyl-carbodiimide; at 0℃; | To a solution of <strong>[105434-90-0]ethyl 5-aminopyrazole-3-carboxylate</strong> (5.00 g, 26.1 mmol) and ethyl hydrogen malonate (3.62 g, 27.4 mmol) in pyridine (130 mL) was added Nu,Nu'- diisopropylcarbodiimide (4.28 g, 33.9 mmol) at 0 C. After being stirred at same temperature, the reaction mixture was poured into water. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol = 19: 1) and triturated with diisopropyl ether to give ethyl 5-[(3-ethoxy-3-oxopropanoyl)amino]- lH-pyrazole-3-carboxylate. MS (APCI): m/z 270 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | There was dissolved, in ethanol (3 mL), <strong>[105434-90-0]ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong></strong> (201 mg, 1.30 mM) and then sodium ethoxide (195 g, 2.86 mM) and diethyl malonate (217 muL, 1.43 mM) were added to the solution. This reaction liquid was stirred for 8 hours, while refluxing the same with heating. This reaction mixture was filtered and then the resulting solid was washed with diethyl ether. After the addition of phosphoryl chloride (10 mL) to the resulting solid with ice-cooling, the resulting suspension was stirred for 3 hours, while refluxing the same with heating. The phosphoryl chloride was distilled off from the reaction liquid, ethanol was then added to the residue with ice-cooling and then the mixture was stirred for 15 minutes. After the concentration of this reaction liquid, the resulting concentrate was purified by the silica gel column chromatography (methanol/methylene chloride=1:100) to thus give the title compound (49.5 mg, overall yield of these two steps: 15%). 1H-NMR (300 MHz, CDCl3): delta 1.45 (t, 3H, J=7.2 Hz), 4.50 (q, 2H, J=7.2 Hz), 7.11 (s, 1H), 7.23 (s, 1H); MS (ESI) m/z 259 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | To a solution of diethyl oxalate (10.0 g, 68.4 mM) in THF (10 mL), there were added 18-crown-6 (1.80 mg, 6.84 mM) and potassium tert-butoxide (1M THF solution, 71.6 mL, 71.6 mM), then acetonitrile (3.99 mL, 75.2 mM) was further added to the mixture at 0 C. and the resulting mixture was stirred for 10 minutes. The temperature of this solution was raised up to 70 C. and it was stirred for 30 minutes at that temperature. The resulting suspension was filtered and the solid was washed with diethyl ether. The resulting solid was suspended in ethanol (100 mL), followed by the addition of water (20 mL), and then concentrated hydrochloric acid (3.0 mL) and methyl carbazinate (3.61 g, 39.7 mM) with ice-cooling and the stirring of the resulting mixture at room temperature for 20 hours. After the completion of the stirring operation, potassium carbonate (2.74 g, 19.8 mM) was added to this suspension and the latter was stirred at 90 C. for 30 minutes. This reaction liquid was concentrated under reduced pressure, the resulting concentrate was diluted with water and the mixture was extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate, the solvent was distilled off and then the resulting solid was sufficiently washed with diethyl ether to thus give the title compound (5.34 g, yield: 50%). 1H-NMR (300 MHz, DMSO): delta 1.23 (t, 3H, J=6.9 Hz), 4.19 (q, 2H, J=6.9 Hz), 4.74-5.12 (br, 2H), 5.64-5.89 (br, 1H), 12.09-12.53 (br, 1H); MS (ESI) m/z 156 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With toluene-4-sulfonic acid; In 5,5-dimethyl-1,3-cyclohexadiene; for 5h;Reflux; Dean-Stark; | Ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[l,5-a]pyrimidine- 2-carboxylate. A suspension of ethyl 5-amino-lH-pyrazole-3-carboxylate (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 mL, 275 mmol) and Ts-OH.H20 (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using Dean-Stork condensor for 5 h.. (Note: The suspension turned clear homogeneous solution and then in about 15 min yellow solid started crashing out of the reaction.). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2-ethoxy-2-oxoethyl)- 7-hydroxy-5-methylpyrazolo[l,5-a]pyrimidine-2-carboxylate (53 g, 75 % yield) as light yellow solid. XH NMR (500MHz, DMSO-d6) delta: 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J= 7.1 Hz, 2H), 4.09 (q, J= 7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H), 1.19 (t, J = 7.0 Hz, 3H). LCMS (M+H) = 308.04. |
75% | With toluene-4-sulfonic acid; In o-xylene; for 5h;Reflux; Dean-Stark; | Ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate [0072] A suspension of <strong>[105434-90-0]ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong></strong> (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 mL, 275 mmol) and TsOH.H2O (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condensor for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (53 g, 75% yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J=7.1 Hz, 2H), 4.09 (q, J=7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J=7.2 Hz, 3H), 1.19 (t, J=7.0 Hz, 3H). LCMS (M+H)=308.04. |
75% | With toluene-4-sulfonic acid; In o-xylene; for 5h;Reflux; Dean-Stark; | A suspension of <strong>[105434-90-0]ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong></strong> (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 mL, 275 mmol) and TsOH*H2O (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condensor for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (53 g, 75 % yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J= 7.1 Hz, 2H), 4.09 (q, J= 7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J= 7.2 Hz, 3H), 1.19 (t, J= 7.0 Hz, 3H). LCMS (M+1) = 308.04. |
75% | With toluene-4-sulfonic acid; In o-xylene; for 5h;Dean-Stark; Reflux; | A suspension of ethyl<strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong> (35.5 g,229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 mL, 275 mmol) and Ts0H?H20 (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condensor for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl6-(2- ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (53 g, 75% yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) 8 12.61 (br. s.,1H), 6.49 (s, 1H), 4.34 (q, J= 7.1 Hz, 2H), 4.09 (q, J= 7.1 Hz, 2H), 3.57 (s, 2H),2.34 (s, 3H), 1.33 (t, J= 7.2 Hz, 3H), 1.19 (t, J= 7.0 Hz, 3H). LCMS (M+1) =308.04. |
75% | With toluene-4-sulfonic acid; In o-xylene; for 5h;Reflux; Dean-Stark; | Ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[l,5-a]pyrimidine- 2-carboxylate. A suspension of ethyl 5-amino-lH-pyrazole-3-carboxylate (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 niL, 275 mmol) and TsOHH20 (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condensor for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2- ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[ 1 ,5-a]pyrimidine-2-carboxylate (53 g, 75 % yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J= 7.1 Hz, 2H), 4.09 (q, J= 7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J= 7.2 Hz, 3H), 1.19 (t, J= 7.0 Hz, 3H). LCMS (M+l) = 308.04. |
75% | With toluene-4-sulfonic acid; In o-xylene; for 5h;Reflux; Dean-Stark; | A suspension of <strong>[105434-90-0]ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong></strong> (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 mL, 275 mmol) and TsOH.H2O (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condenser for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (53 g, 75% yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J=7.1 Hz, 2H), 4.09 (q, J=7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J=7.2 Hz, 3H), 1.19 (t, J=7.0 Hz, 3H). LCMS (M+1)=308.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at -10 - 20℃; | General procedure: To a cooled (-10 C) mixture containing 5-amino-1H-pyrazole (0.65 mmol) and potassium carbonate (1.00 mmol) in 3.0 mL of anhydrous DMF was added dropwise a solution of the acid chloride (0.50 mmol) in 2.0 mL of DMF. The reaction was stirred at -10C for 15 minutes, and then gradually warmed to room temperature. After stirring at room temperature for 15minutes, TLC indicated that acylation of the amino group was complete. The reaction was then immersed in a preheated oil bath at 140-145 Cuntil the ring closure was complete (30 min-1h). The reaction mass was cooled to room temperature and concentrated to dryness under vacuum. The crude product was slurried in deionized water, filtered, and the resulting solid was washed with methanol:ether (2:1). Alternatively, some cases required column chromatography, which was done on silica using methanol:dichloromethane (1:9) as the eluent [ethanol:dichloromethane (1:9) was used for the product having the ethyl ester]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at -10 - 20℃; | General procedure: To a cooled (-10 C) mixture containing 5-amino-1H-pyrazole (0.65 mmol) and potassium carbonate (1.00 mmol) in 3.0 mL of anhydrous DMF was added dropwise a solution of the acid chloride (0.50 mmol) in 2.0 mL of DMF. The reaction was stirred at -10C for 15 minutes, and then gradually warmed to room temperature. After stirring at room temperature for 15minutes, TLC indicated that acylation of the amino group was complete. The reaction was then immersed in a preheated oil bath at 140-145 Cuntil the ring closure was complete (30 min-1h). The reaction mass was cooled to room temperature and concentrated to dryness under vacuum. The crude product was slurried in deionized water, filtered, and the resulting solid was washed with methanol:ether (2:1). Alternatively, some cases required column chromatography, which was done on silica using methanol:dichloromethane (1:9) as the eluent [ethanol:dichloromethane (1:9) was used for the product having the ethyl ester]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
a solution of a C^ (0.94 g, 0.014 mol) in water (4 mL) was added drop wise was added slowly to a cold (0 C) suspension of ethyl 5-amino-lH-pyrazole-3-carboxylate (2 g, 0.0129 mol) in 6N HCI (8 mL) keeping the temperature below 5 C. The resultant reaction mixture was stirred at 5-10 C for 1 h. A solution of SO2 was prepared by bubbling the gas into AcOH (12.8 mL) until the solution gained at least 0.8 g in weight and then a solution of Q1Q2 (0.69 g, 0.0051 mol) in 3 mL of water was added and stirred for 10 minutes. Then the diazotized solution was added to SO2 gas solution at room temperature and stirred at room temperature for 20 minutes. The reaction mixture was diluted with water and extracted with diethyl ether (20 mL x 2). Combined organic layers were washed with water, brine, dried over Na2S04 and concentrated under reduced pressure to afford crude product (1.2 g, 40%) as off white solid. The crude off-white solid was directly used for next step without purification. XH NMR (400 MHz, CDCI3): delta 11.69 (br, 1H), 7.38 (s, 1H), 4.45 (q, J= 7.1 Hz, 2H), 1.42 (t, J= 7.1 Hz, 3H); LC-MS: [M-H]" = 236.9 m/z. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23 mg | LAH (20 mg, 0.51 mmol) was added to an ice cooled solution of ethyl 5-amino-l-((2-(5-phenylisoxazole-3-carboxamido)ethyl)sulfonyl)-lH- pyrazole-3-carboxylate (100 mg, 0.2537 mmol) in THF (10 mL) and the reaction mixture was stirred for 1 h at the same temperature. Then the reaction mixture was quenched with saturated NH4C1 solution and filtered through celite pad. The filtrate was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude compound which was further purified by preparative HPLC to obtain N-(2-((5-amino-3-(hydroxymethyl)-lH-pyrazol-l- yl)sulfonyl)ethyl)-5-phenylisoxazole-3-carboxamide (23 mg, 7% over two steps). (0261) [00169] Appearance: white solid (0262) [00170] Analytical data: XH NMR (400 MHz, DMSO-d6): delta 8.89-8.87 (m, IH), 7.94-7.92 (m, 2H), 7.58-7.54 (m, 3H), 7.36 (s, IH), 6.07 (s, D20 exchangeable, 2H), 5.34 (s, IH), 5.16 (t, J=6.0 Hz, IH), 4.25 (d, J=6.0 Hz, 2H), 3.76 (t, J=6.6 Hz, 2H), 3.61-3.56 (m, 2H). (0263) [00171] LC-MS: [M+H]+=391.9 (0264) [00172] HPLC Purity: 98.50% at 254 nm and 98.37% at 220 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; for 2h; | ethyl 5-amino-lH-pyrazole-3-carboxylate (124 mg, 0.794 mol) was added to a cold solution of 2-(5-phenylisoxazole-3-carboxamido)ethane-l-sulfonyl chloride (250 mg, 0.794 mmol) in DCM (20 mL) followed by addition of Et3N (160 mg, 1.589 mmol) and the resulting reaction mixture was stirred at room temperature for 2h. Volatiles were removed under reduced pressure to obtain crude compound which was chromatographed on silica gel (mesh 100-200) using 50% EtOAc in hexane as eluent to obtain mixture of isomeric products (120 mg, crude) as off white sticky solid. LC-MS: [M+H]+=434.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With acetic acid;Reflux; | Step 1. Synthesis of ethyl pyrazolo[1 ,5-a]pyrimidine-2-carboxylate (C1). A mixture of ethyl 5-amino-1/-/-pyrazole-3-carboxylate (64 g, 0.41 mol) and 1 , 1 ,3,3- tetraethoxypropane (91 g, 0.41 mol) in acetic acid (400 ml_) was heated at reflux overnight. After removal of solvent in vacuo, the pH was adjusted to 8 with saturated aqueous sodium bicarbonate solution. The resulting mixture was extracted with dichloromethane, and the combined organic layers were dried, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 1 % to 99% dichloromethane in petroleum ether) afforded the product as a light yellow solid. Yield: 17.4 g, 91.0 mmol, 22%. 1 H N MR (400 MHz, CDCI3) delta 8.76 (ddd, J=7.2, 1.6, 0.9 Hz, 1 H), 8.58 (dd, J=4.0, 1.7 Hz, 1 H), 7.25 (br s, 1 H), 6.96 (dd, J=7.1 , 4.0 Hz, 1 H), 4.51 (q, J=7.2 Hz, 2H), 1.46 (t, J=7.2 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | To a solution of ethyl 5-amino-lH-pyrazole-3-carboxylate (500 mg, 3.54 mmol) in HBr (10 mL, 40%) was added a solution of NaN02(269 mg, 3.90 mmol) in water (2 mL) at 0C. The resulting solution was stirred for 10 min at 0C. Then CuBr (1.5 g, 10.5 mmol) was added batchwise to the reaction. The mixture was stirred for 15 min at 0C. The solids were filtered out. The resulting solution was extracted with 3x10 mL of dichloromethane. The organic layers were combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 10). This resulted in 260 mg (36%) of the title compound as a white solid. LC-MS (ESI, m/z): [M+H]+= 219.1, 221.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of Intermediate 1A (291 mg, 1.27 mmol), <strong>[105434-90-0]ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong></strong> (200 mg, 1.01 mmol) and 2,3-dihydrobenzo[1,4]dioxine-2-carbaldehyde (300 mg, 1.29 mmol) in DMF (1 mL) was heated at 120 C. for 2 h. The reaction mixture was allowed to cool to RT and then poured onto ice. The solid formed was filtered off, washed with water and dried in a desiccator at 50 C. overnight. The crude material was chromatographed on a Si cartridge eluting with 0-10% methanol in DCM. Evaporation gave a yellow oil (383 mg, 0.75 mmol) which was dissolved in THF (9 mL). The solution was cooled to 0 C. under argon and 2M lithium aluminium hydride (1.12 mL, 2.25 mmol) was added dropwise. The reaction was allowed to warm slowly to RT and, after 3 h, it was quenched by the addition of water (1 mL) and 1N sodium hydroxide (0.4 mL). The mixture was diluted with THF and filtered through Celite. The solid cake was washed with 10% methanol in DCM and the filtrate was evaporated to give an orange oil. The crude material was chromatographed on a 25 g Si cartridge eluting with 0-10% methanol in ethyl acetate. The mixture of four stereoisomers was obtained as a yellow solid (136 mg). The isomers were separated by SFC using the conditions below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.25 g | With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 70℃; | Ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong> (1.55 g, 10 mmol), tert-butyl acetoacetate (1.65 mL, 10 mmol), 3-fluoro-(4-trifluoromethyl)benzaldehyde (1.92 g, 10 mmol) and sodium bicarbonate (2.52 g, 30 mmol) were heated at 70 C. in DMF (3 mL) overnight. The reaction mixture was allowed to cool then partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was further extracted with ethyl acetate (20 mL) and the combined organics were dried by passing through a hydrophobic fit, and evaporated to give an orange oil. The residue was dissolved in a minimum amount of DCM and loaded onto a 50 g Si cartridge. The product was eluted with 0-50% ethyl acetate in cyclohexane. The fractions containing the desired product were combined and evaporated to give a pale yellow solid. The solid was triturated with ethyl acetate/cyclohexane to give a white solid (1.25 g). LCMS (Method 3): Rt=1.36 min, m/z 470.5 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62 mg | In N,N-dimethyl-formamide; at 120℃; for 3h; | A mixture of Intermediate 1A (398 mg, 1.74 mmol), <strong>[105434-90-0]ethyl <strong>[105434-90-0]5-amino-1H-pyrazole-3-carboxylate</strong></strong> (295 mg, 1.9 mmol) and 4-(trifluoromethyl)benzaldehyde (330 mg, 1.9 mmol) in DMF (3 mL) was heated at 120 C. for 3 h. The reaction mixture was allowed to cool to RT and LiCl (4% aq, 10 mL) was added followed by DCM (10 mL). The organic phase, which contained a suspension of solid material, was separated and then filtered. The solution was dried (Na2SO4) and evaporated to give the desired product as an off-white solid (330 mg). |
Tags: 105434-90-0 synthesis path| 105434-90-0 SDS| 105434-90-0 COA| 105434-90-0 purity| 105434-90-0 application| 105434-90-0 NMR| 105434-90-0 COA| 105434-90-0 structure
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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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