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CAS No. : | 1904-24-1 | MDL No. : | MFCD08060982 |
Formula : | C5H9N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AXDGPQLEVYSXNL-UHFFFAOYSA-N |
M.W : | 111.15 | Pubchem ID : | 21991095 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
78% | With hydrazine hydrate In ethanol for 12 h; Reflux | To a stirred solution of 3-oxopentanenitrile (XXXV; 2g; 21 mmol) in ethanol (60 mL) was added hydrazine hydrate (1.3 mL; 41 mmol). The reaction mixture was heated to a reflux for12 hours. The reaction mixture was cooled and concentrated under reduced pressure. The crude mixture was purified by column chromatography using 8percent MeOH-DCM to obtain 5-ethyl-1H- pyrazol-3-amine as a brown sticky solid (XXXVI; 1.8 g; 78percent yield). ‘H NMR (400 MHz,DMSO-d6): ö 11.0 (bs, 1H), 5.17 (s, 1H), 4.5 (bs, 2H), 2.4 (m, 2H), 1.1 (m, 3H). MS (M+1):111.93. |
51% | With hydrazine In ethanol at 70℃; for 12 h; | A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 70°C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51percent yield; 1H NMR: (DMSOd6) 1.04 (t, 3H)5 2.41 (q, 2H), 4.4 (br s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(A) In the same manner as described in the step (A) of Reference Example 19, 9.97 g of N-(5-ethyl-1H-pyrazol-3-yl)acetamidine hydrochloride was obtained from 12.9 g of <strong>[1904-24-1]3-amino-5-ethyl-1H-pyrazole</strong> and 16.3 g of ethyl acetimidate hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With triethylamine; In ethanol; at 20℃; for 3.0h; | Example 148 (5-Ethyl-2H-pyrazol-3-yl)-[2-(5-ethyl-2H-pyrazol-3-ylamino)-quinazolin-4-yl]-amine (IIc-69) To a solution of 2,4-dichloroquinazoline (0.5 g, 2.51 mmol) and 3-amino-S-ethylpyrazole (558 mg, 5.02 mmol) in ethanol (10 mL) was added triethylamine (0.35 mL, 2.51 mmol) and the resulting mixture-was stirred for 3-hours at room temperature. The resulting pale yellow precipitate was collected by filtration, washed with cold ethanol and dried under vacuum to afford IIc-69 (306 mg, 35%) as an off-white solid, mp 248-252 C.; 1H NMR (DMSO 31.30 (m, 6H), 2.72 (m, 4H), 6.12 (br.s, 1H), 6.54 and 6.90 (br. s, 1H), 7.58 (t, 1H), 7.74 (d, 1H), 7.90 (t, 1H), -8.78 (d, 1H); IR (solid) 1639, 1602, 1591, 1555, 1418; MS 349.2 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 60℃; for 18.0h; | Method 65; 4- (5-Ethvl-lH-pyrazol-3-vlamino)-2-chloropyrimidine A mixture of 2, 4-dichloropyrimidine (2.97g, 20mmol), 5-amino-3-ethyl-1H-pyrazole (2.44g, 22mmol) and N, N-diisopropylethylamine (3. 8ml, 22mmol) in dry THF (75ml) was heated at 60C for 18 hours. The volatiles were removed by evaporation, and the residue was triturated with a mixture of DCM and water. The solid product was collected by filtration, washed with water and ether, and dried to give the title compound (1.55g, 35%) as a colourless crystalline solid. NMR (DMSO): 1.20 (t, 3H), 2.60 (q, 2H), 6.06 (s, 1H), 7.15 (s, 1H), 8.10 (d, 1H), 9.80 (s, 1H), 11.83 (br s, 1H); m/z 224 [MH] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With sodium carbonate; In ethanol; at 40 - 55℃; | Method 79; 6-Ethyl-2-chloro-4- (5-ethyl-lH-pvrazol-3-ylamino) pyrimidine 2,4-Dichloro-6-ethyl-pyrimidine (J. Am. Chem. Soc. 1936, 58, 78) (1.33g 7.53mmol) was stirred in ethanol (50ml) and 5-ethyl-lH-3-amino-pyrazole (Method 6 of WO 03/048133) (0. 836g, 7.53mmol) was added followed by sodium carbonate (1.25g) and the mixture stirred at 40C for 4 days then at 55C overnight. The insoluble inorganics were removed by filtration and solvent removed from the filtrate by evaporation. Water (100ml) was added and the mixture extracted with EtOAc (3 x 50ml). The extracts were combined and washed with water (50ml), brine (50ml), dried (MgS04) and solvent removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (100: 0 increasing in polarity to 0: 100) to give the title compound (210mg, 11%) a white solid. NMR (DMSO-d6 at 100C) : 1.20 (m, 6H), 2.50-2. 70 (m, 4H), 6.05 (s, 1H), 7.05 (br s, 1H), 9.70 (br s, 1H), 11.85 (br s, 1H) ; m/z 252 [MH] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | In 1,4-dioxane; dichloromethane; | A. 4-(2,4-dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine A mixture of <strong>[1904-24-1]3-amino-5-ethylpyrazole</strong> (10.3 g, 39.3 mmol) and N-(1-(methylthio)ethylidene)-2,4-dichloro-benzamide (4.0 g, 35.7 mmol) in anhydrous dioxan (20 mL) was stirred at reflux temperatrue under a nitrogen atmosphere for 16 h. After being cooled to ambient temperature, the reaction mix was concentrated in vacuo and the residue was treated with dichloromethane. The resulting supsension was filtered and the filtrate was concentrated in vacuo to afford an oil (1.5 g, 14% yield): NMR (CDCl3, 300 MHz): delta 7.62 (d, 1H, J=8), 7.59 (d, 1H, J=2), 7.45 (dd, 1H, J=8,2), 6.42 (s, 1H), 2.82 (q, 2H, J=8), 2.73 (s, 3H), 1.30 (t, 3H, J=8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(A) In the same manner as described in the step (A) of Reference Example 18, 15.8 g of N-(5-ethyl-1H-pyrazol-3-yl)butylamidine hydrochloride was obtained from 13.7 g of <strong>[1904-24-1]3-amino-5-ethyl-1H-pyrazole</strong> and 21.1 g of ethyl butylimidate hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With hydrazine hydrate; In ethanol; for 12.0h;Reflux; | To a stirred solution of 3-oxopentanenitrile (XXXV; 2g; 21 mmol) in ethanol (60 mL) was added hydrazine hydrate (1.3 mL; 41 mmol). The reaction mixture was heated to a reflux for12 hours. The reaction mixture was cooled and concentrated under reduced pressure. The crude mixture was purified by column chromatography using 8% MeOH-DCM to obtain 5-ethyl-1H- pyrazol-3-amine as a brown sticky solid (XXXVI; 1.8 g; 78% yield). ?H NMR (400 MHz,DMSO-d6): oe 11.0 (bs, 1H), 5.17 (s, 1H), 4.5 (bs, 2H), 2.4 (m, 2H), 1.1 (m, 3H). MS (M+1):111.93. |
51% | With hydrazine; In ethanol; at 70℃; for 12.0h; | A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 70C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR: (DMSOd6) 1.04 (t, 3H)5 2.41 (q, 2H), 4.4 (br s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With hydrazine; In ethanol; for 1h;Heating / reflux; | 2B. Preparation of 3-ethyl-1H-pyrazol-5-amine To a mixture of <strong>[33279-01-5]3-oxopentanenitrile</strong> in ethanol (5 mL), was added hydrazine (0.2 mL, 6 mmol). The mixture was refluxed for 1 h, and then concentrated under reduced pressure. The residue was diluted with methanol (1 mL) and purified by preparative reversed-phase HPLC (YMC ODS-A 5 um 30*100 mm, 10-90% aqueous methanol containing 0.1% TFA, 15 min gradient, monitored at 220 nm) to give 3-ethyl-1H-pyrazol-5-amine (0.3 g, 68%). 1H-NMR (MeOD) delta 5.54 (s, 1H), 2.60 (q, 2H, J=7.6 Hz), 1.25 (t, 3H, J=7.6 Hz). |
68% | With hydrazine; In ethanol; for 1h;Reflux; | To a mixture of <strong>[33279-01-5]3-oxopentanenitrile</strong> in ethanol (5 mL), was added hydrazine (0.2 mL, 6 mmol). The mixture was refluxed for Ih, and then concentrated under reduced pressure. The residue was diluted with methanol (1 mL) and purified by preparative reversed-phase HPLC (YMC ODS-A 5um 30 x 100 mm, 10-90% aqueous methanol containing 0.1% TFA, 15 min gradient, monitored at 220 nm) to give 3-ethyl- lH-pyrazol-5-amine (0.3 g, 68%). 1HNMR (MeOD) delta 5.54 (s, IH), 2.60 (q, 2H, J= 7.6 Hz), 1.25 (t, 3H, J= 7.6 Hz). |
51% | With hydrazine; In ethanol; at 70℃; for 12h; | A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 700C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR: (DMSOd6) 1.04 (t, 3H), 2.41 (q, 2H), 4.4 (br s, 2H). |
51% | With hydrazine; In ethanol; at 70℃; for 12h; | A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 70C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR: (DMSOd6) 1.04 (t, 3H)5 2.41 (q, 2H), 4.4 (br s, 2H). |
51% | With hydrazine; In ethanol; hexane; at 70℃; for 12h; | A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 7O0C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR Spectrum: (DMSOd6) 1.04 (t, 3H), 2.41 (q, 2H), 4.4 (br s, 2H). |
51% | With hydrazine; In ethanol; water; at 70℃; for 12h; | A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 7O0C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19: 1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR Spectrum: (DMSOd6) 1.04 (t, 3H), 2.41 (q, 2H), 4.4 (br s, 2H). |
49% | With hydrazine hydrate; In methanol; at 150℃; for 0.0833333h;Microwave irradiation; | General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With triethylamine; In isopropyl alcohol;Heating / reflux; | 3-((2,6-Dichloropyrimidin-4-yl)methyl)benzonitrile 10c (646 mg, 2.46 mmol), 5-Ethyl-1H- pyrazol-3-ylamine 10d (300 mg, 2.70 mmol) and TEA (0.60 mL, 4.3 mmol) were dissolved in isopropanol (25 mL) and refluxed for overnight. Solvent was removed by vacuum. Ethyl acetate and water were added to the residue. The EA phase was separated, washed with brine and dried over sodium sulfate. Purification by Biotage (0 to 60% ethyl acetate in hexane) gave compound 10e (443 mg, 53%). LCMS (APCI, M+H+): 339.0. 1H NMR (400MHz, DMSO-d6): delta 1.10 (t, J=7.5 Hz, 3H), 2.50 (q, J=7.9 Hz, 2H), 3.91 (s, 2H), 7.47 (t, J=7.6 Hz, 1 H), 7.55 (d, J=8.4 Hz, 1 H), 7.66 (d, J=7.9 Hz, 1 H), 7.70 (s, 1 H), 10.18 (s, 1 H), 12.06 (s, 1 H).A microwave reaction vessel was charged with 3-((2-Chloro-6-(5-ethyl-1H-pyrazol-3- ylamino)pyrimidin-4-yl)methyl)benzonitrile 10e (140 mg, 0.414 mmol), AXL012352 (86 mg, 0.435 mmol) compound 1f, TEA (0.12 mL, 0.83 mmol) and amyl alcohol (3 mL). It was sealed and then heated in a Biotage Smith Synthesizer microwave at 2000C for 20 minutes. Purification by Biotage (0 to 80% ethyl acetate in hexane) gave compound 10 as a light yellow solid (78 mg, 38%). LCMS (APCI, M+H+): 501.3. 1H NMR (400MHz, DMSO- d6): delta 1.21 (t, J=7.6 Hz, 3H), 1.42 (s, 9H), 2.18 (s, 1 H), 2.56-2.65 (m, 2H), 3.43-3.53 (m, EPO <DP n="74"/>2H), 3.80 (s, 4H), 7.65 (t, J=7.8 Hz, 1H), 7.69 (d, J=7.8 Hz1 1H), 7.73 (d, J=7.6 Hz, 1H),7.80 (S, 1 H), 9.38 (s, 1 H), 11.89 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetic acid; at 120℃; for 4.0h; | Example 36: 5-(2,3-Difluoro-benzylsulfanyl)-2-ethyl-pyrazolo[1 ,5-a]pyrimidin-7-olA mixture of 52 mg of 4-(2,3-difluoro-phenylsulfanyl)-3-oxo-butyric acid methyl ester (Intermediate A) and 20 mg of 5-ethyl-1 H-pyrazol-3-ylamine in 0.8 ml of glacial AcOH is heated at 120 for 4 hours. During cooling to RT a product crystallizes out of the solution obtained. A precipitate obtained is filtered off, washed with Et2O and dried. The title compound is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In 1,4-dioxane; for 24.0h;Heating / reflux; | Intermediate 1 : 2-(5-ethyl-1 H-pyrazol-3-yl)-1 H-isoindole-1 ,3(2H)-dione; To a solution of 5-ethyl-1 H-pyrazol-3-amine (1 g, 9 mmol) in dioxane (50 mL) was added phthalic anhydride (1.4 g, 1.05 eq.) and the reaction mixture was stirred at reflux for 24 hours. The solution was evaporated under reduced pressure leading to a solid which was triturated in cyclohexane. After filtration and dry the title compound was obtained as a yellow solid (2 g, 100%). LC/MS: m/z 242 (M+H)+, Rt: 2.56 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; potassium iodide; In N,N-dimethyl-formamide; at 20℃; | [00436] Step A: To a mixture of 5-ethyl-lH-pyrazol-3-amine (101 mg, 0.91 mmol), potassium iodide (117 mg, 0.7 mmol), and DIEA (0.15 mL, 0.84 mmol) in DMF (4 mL) was added (4-chloroquinazolin-2-yl)(4-fluorophenyl)methanone from Example 3 Step A (200 mg, 0.7 mmol) and the mixture was stirred at rt overnight. Water was added and the precipitated solid was collected by filtration. The yellow solid (226 mg) containing (4-(5-ethyl-lH-pyrazol-3-ylamino)quinazolin-2-yl)(4- fluorophenyl)methanone was used directly in the next step. LC-MS (ESI) m/z 362 (M + H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.6% | With acetic acid; In water; at 0 - 100℃; | Compound B-26[0984] Step 1 : Synthesis of ethyl 3-ethyl-6-hydroxy-lH-pyrazolo[3,4-b]pyridine-4- carboxylate[0985] A stirred solution of 5-ethyl-lH-pyrazol-3-amine (1 g, 9.00 mmol) in acetic acid (6.6 niL) and water (20 niL) was cooled to 0 C and diethyl oxaloacetate sodium salt (1.88 g, 9.00 mmol) was added to it. Resulting solution was heated at 100 C for overnight. After completion of the reaction, the solid was filtered and dried to obtain the desiredintermediate (0.52 g, 24.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; for 2.0h;Inert atmosphere; Reflux; | Example 122a 5-Bromo-3-(5-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one 122a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (80 mL), <strong>[1904-24-1]5-ethyl-1H-pyrazol-3-amine</strong> (3.33 g, 30.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (9.6 g, 36 mmol), and cesium carbonate (19.5 g, 60 mmol). After bubbling nitrogen through the suspension for 10 minutes, Xantphos (1.73 mg, 3.0 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.36 mg, 1.5 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 2 h. It was then filtered immediately. The solid was washed with dioxane (3*30 mL) and the combined filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (2:1 to 1:2) to afford 122a (3.8 g, 43%) as a red solid. MS-ESI: [M+H]+ 297.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 2.0h;Inert atmosphere; Reflux; | Example 127a 6-Chloro-2-methyl-4-(5-methyl-1H-pyrazol-3-ylamino)pyridazin-3(2H)-one 127a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (20 mL), <strong>[1904-24-1]5-ethyl-1H-pyrazol-3-amine</strong> (971 mg, 10.0 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (2.46 g, 11.0 mmol), and cesium carbonate (6.52 g, 20.0 mmol). After bubbling nitrogen through the suspension for 10 minutes, xantphos (1.74 g, 3.0 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.37 g, 1.5 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 2 h. It was then filtered immediately when the reaction mixture was still hot. The solid was washed with dioxane (3*30 mL) and the combined filtrate was concentrated under reduced pressure. The residue was purified by silica-gel chromatography eluting with 6:1 petroleum ether/ethyl acetate to afford 127a (1.8 g, 75%) as a yellow solid. MS-ESI: [M+H]+ 239.9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With acetic acid; In toluene; at 140℃; for 0.666667h;Microwave irradiation; | To a stirred solution of <strong>[1904-24-1]5-ethyl-1H-pyrazol-3-amine</strong> (XXXVI; 1.65g; 15 mmol) and 3- (diethylamino)acrylonitrile (II; 2.76g; 22 mmol) in toluene (22 mL) was added acetic acid (27 mL). The reaction mixture was heated at 140C in a microwave for 40 minutes. The reaction mixture was cooled and concentrated under reduced pressure. The crude mixture was purifiedby column chromatography using 6% MeOH-DCM to obtain 2-ethylpyrazolo[1,5-a]pyrimidin-7-amine as a sticky brown solid (XXXVII; 1 .7g; 70% yield). ?H NMR (400 MHz, DMSU-cI):6 7.97-7.96 (d, J = 5.2 Hz, 1H), 7.57 (bs, 2H), 6.18 (s, 1H), 5.99-5.98 (d, J = 5.2 Hz, 1H),2.77-2.71 (q,J= 7.6 Hz, 2H), 1.28-1.24 (t,J= 7.6 Hz, 3H). MS (M+1): 162.96. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 20 - 60℃; for 5.0h; | 2,4-Dichloro-5-methoxypyrimidine (2.79 mmol, 0.50 g) and the compound prepared in Step 1 (3.07 mmol) were stirred at room temperature DIPEA (N, N-diisopropylethylamine) was added to isopropanol (30 ml), and the mixture was stirred and heated to 60 C for 5 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Methanol/dichloromethane To give the desired compound in 68% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29 mg | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 18.0h; | 30 mg of 4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid obtained in step 2 of Reference Example 1, 16 mg of <strong>[1904-24-1]5-ethyl-1H-pyrazol-3-amine</strong>, and 55 mg of HATU were dissolved in 1 mL of DMF, and 62 muL of diisopropylethylamine was added thereto. The mixture was stirred at room temperature for 18 hours, and water was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, followed by concentration of the organic solution under reduced pressure. The residue was purified by silica gel chromatography (chloroform?chloroform/methanol=10/1), thereby obtaining 29 mg of the title compound as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With dmap; triethylamine; In tetrahydrofuran; at 0 - 20℃; | To a solution of <strong>[1904-24-1]5-ethyl-1H-pyrazol-3-amine</strong> (16.7 g, 150 mmol) in THF (350 mL) was added triethylamine (21 ml, 150 mmol), DMAP (1.84 g, 15.0 mmol) and di-tert-butyl dicarbonate (32.8 g, 150 mmol). The resulting mixture was stirred at 0C for 2h and overnight at room temperature. The solution was diluted with water (100 mL) and extracted with ethyl acetate (3 x 100 mL) to yield after evaporation in vaccuo 32.5 g of the crude product. Purification by Biotage Isolera chromatography (silica gel, hexane - ethyl acetate) yielded after evaporation and trituration with hexane, 5.61 g (18 %) of the title compound as the minor isomer. LC-MS (Method G): Rt = 0.92 min; MS (ESIpos): m/z = 212 [M+H]+ 1-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.1 14 (1.41), 1.133 (3.08), 1.151 (1.46), 1.504 (16.00), 2.750 (0.93), 2.753 (0.91), 2.769 (0.90), 2.771 (0.89), 5.300 (1.36), 5.589 (1.44). |
Tags: 1904-24-1 synthesis path| 1904-24-1 SDS| 1904-24-1 COA| 1904-24-1 purity| 1904-24-1 application| 1904-24-1 NMR| 1904-24-1 COA| 1904-24-1 structure
[ 174891-10-2 ]
5-Amino-1H-pyrazole-3-acetic acid
Similarity: 0.76
[ 5453-07-6 ]
5-Amino-3-methyl-1H-pyrazole-4-carbonitrile
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[ 174891-10-2 ]
5-Amino-1H-pyrazole-3-acetic acid
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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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