1-Methyl-1H-pyrazole-5-carboxylic acid CAS#: 16034-46-1; 凯望编码 (ChemWhat Code): 158345
Identification
| 英文名 | 1-Methyl-1H-pyrazole-5-carboxylic acid |
| IUPAC Name | 2-methylpyrazole-3-carboxylic acid |
| 分子结构 |  |
| CAS编号 | 16034-46-1 |
| 别名 | 1-methyl-1H-pyrazole-5-carboxylic acid 16034-46-1 2-methylpyrazole-3-carboxylic acid 1H-pyrazole-5-carboxylic acid, 1-methyl- DTXSID50349118 DTXCID20300190 673-167-6 inchi=1/c5h6n2o2/c1-7-4(5(8)9)2-3-6-7/h2-3h,1h3,(h,8,9 1-methylpyrazole-5-carboxylic acid 2-Methyl-2H-pyrazole-3-carboxylic acid MFCD00464253 1-METHYL-5-PYRAZOLECARBOXYLIC ACID CHEBI:74737 1-methyl-pyrazole-5-carboxylic acid 5-Carboxy-1-methyl-1H-pyrazole 1-Methyl-1H-pyrazole-5-carboxylicacid SCHEMBL262323 SCHEMBL2440450 SCHEMBL3420777 CHEMBL2287221 ALBB-000283 CS-D1713 SBB000007 STK301313 5-Pyrazolecarboxylic acid, 1-methyl- AKOS000301200 1-methyl-1H-pyrazol-5-carboxylic acid AC-7334 FM56316 PB26026 PS-5369 HY-34505 ST005602 SY005770 2H-Pyrazole-3-carboxylic acid, 2-methyl- DB-025018 M2494 EN300-31077 1-Methyl-1H-pyrazole-5-carboxylic acid, 97% Q27144865 Z275167524 |
| 分子式 | C5H6N2O2 |
| 分子量 | 126.11 |
| InChI | InChI=1S/C5H6N2O2/c1-7-4(5(8)9)2-3-6-7/h2-3H,1H3,(H,8,9) |
| InChI Key | JREJQAWGQCMSIY-UHFFFAOYSA-N |
| SMILES | CN1C(=CC=N1)C(=O)O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN117794527 | Novel AMP-activating protein kinase activators | 2024 |
| WO2021/239745 | IL-17A MODULATORS | 2021 |
| WO2021/255085 | SMALL MOLECULE MODULATORS OF IL-17 | 2021 |
| WO2020/43880 | HETEROCYCLIC COMPOUNDS AS AHR MODULATORS | 2020 |
| WO2020/127685 | AMINO-ACID ANILIDES AS SMALL MOLECULE MODULATORS OF IL-17 | 2020 |
| WO2018/11201 | HETEROAROMATIC MODULATORS OF THE RETINOID-RELATED ORPHAN RECEPTOR GAMMA | 2018 |
Physical Data
| Appearance | White powder |
| Melting Point, °C |
| 222 – 225 |
| 222 – 224 |
| 221 |
| 221 – 222 |
| 222 – 223 |
| 223 – 224 |
| 222 |
| Boiling Point, °C |
| 251 |
| 250 – 252 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 24.84 | |
| Chemical shifts, Spectrum | 13C | dimethylsulfoxide-d6 | 24.84 | |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 500 | |
| Chemical shifts | 13C | dimethylsulfoxide-d6 | 126 | |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 21.24 | 400 |
| Chemical shifts, Spectrum | 13C | dimethylsulfoxide-d6 | 19.84 | 100 |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 300 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| Bands | KBr |
| Description (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| methanol | 259 | 6490 |
Route of Synthesis (ROS)
| Conditions | Yield |
| With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 – 20℃; for 16h; Inert atmosphere; Experimental Procedure Synthesis of N-methoxy-N, 1-dimethyl-1H-pyrazole-5-carboxamide (27) To a stirred solution of compound 26 (12 g, 95.23 mmol) in CH2Cl2 (600 mL) under inert atmosphere were added N, O-dimethylhydroxylamine hydrochloride (10.26 g, 104.76 mmol), EDCI.HCl (19.2 g, 100.00 mmol), DMAP (12.8 g, 104.91 mmol), and N-methylmorpholine (12.8 mL, 11.54 mmol) at 0 oC, followed by warming to room temperature and stirring for 16 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and extracted using EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel flash column chromatography using 10% EtOAc/ hexanes to afford compound 27 (12 g, 75%) as brown liquid. TLC: 20% EtOAc/ hexanes (Rf: 0.8); 1H NMR (400 MHz, CDCl3): δ 7.48 (d, J = 2.0 Hz, 1H), 6.77 (d, J = 2.0 Hz, 1H), 4.13 (s, 3H), 3.66 (s, 3H), 3.36 (s, 3H); LCMS Calculated for C7H11N3O2: 169.09; Observed: 169.9 (M+1)+. | 75% |
| With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; Experimental Procedure 21.1 1) 1-Methyl-N′-[4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-carbohydrazide 1) N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide N,O-dimethylhydroxylamine hydrochloride (1.30 g) was added to an dimethylformamide (32 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (1.21 g), O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (4.38 g) and diisopropylethylamine (3.34 mL) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=100:0 to 95:5), so as to obtain the title compound (1.03 g) in the form of a yellow oily substance. 1H NMR (200 MHz, CHLOROFORM-d) δ ppm 3.36 (s, 3H) 3.66 (s, 3H) 4.13 (s, 3H) 6.77 (d, J=2.20 Hz, 1H) 7.48 (d, J=2.20 Hz, 1H); MS (ESI pos.) m/z: 170 [M+H]+ | 1.03 g |
| With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; Experimental Procedure 14.1 1) N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide 1) N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide N,O-dimethylhydroxylamine hydrochloride (1.30 g) was added to an N,N-dimethylformamide (32 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (1.21 g), O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (4.38 g) and diisopropylethylamine (3.34 mL) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=100:0 to 95:5), so as to obtain the title compound (1.03 g) in the form of a yellow oily substance. 1H NMR (200 MHz, CHLOROFORM-d) δ ppm 3.36 (s, 3H) 3.66 (s, 3H) 4.13 (s, 3H) 6.77 (d, J=2.20 Hz, 1H) 7.48 (d, J=2.20 Hz, 1H); MS (ESI pos.) m/z: 170 [M+H]+ | 1.03 g |
| Stage #1: 1-methyl-1H-pyrazole-5-carboxylic acid With 1,1′-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; | |
| 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 dichloromethane at 20℃; for 18h; Inert atmosphere; Experimental Procedure 94.1 1) Preparation of intermediate 153-2 At room temperature, 153-1 (1.0 g, 7.93 mmol), N,O-dimethylhydroxylamine hydrochloride (0.93 g, 9.52 mmol), diisopropylethylamine (4.10 g, 31.72 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazole-1-yl)urea hexafluorophosphate (3.62 g, 9.52 mmol) and dichloromethane (20.0 mL) were added to a single-mouth bottle. The reaction was carried out at room temperature for 18 hours, and the reaction solution was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 100: 1 to 5: 1) to obtain a yellow solid intermediate 153-2 (1.3 g) | 1.03 g |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (93.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 126.115 |
| logP | 0.225 |
| HBA | 4 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 55.12 |
| Rotatable Bond (RotB) | 1 |
| Matching Veber Rules | 2 |
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