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CAS No. : | 75092-30-7 | MDL No. : | MFCD00461121 |
Formula : | C5H5IN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SZRMOKQNOJYMNK-UHFFFAOYSA-N |
M.W : | 252.01 | Pubchem ID : | 673687 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.17 |
TPSA : | 55.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.31 cm/s |
Log Po/w (iLOGP) : | 1.13 |
Log Po/w (XLOGP3) : | 0.74 |
Log Po/w (WLOGP) : | 0.72 |
Log Po/w (MLOGP) : | 0.6 |
Log Po/w (SILICOS-IT) : | 0.73 |
Consensus Log Po/w : | 0.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.17 |
Solubility : | 1.69 mg/ml ; 0.00672 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.48 |
Solubility : | 8.41 mg/ml ; 0.0334 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.13 |
Solubility : | 18.9 mg/ml ; 0.0748 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.75 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
47.5% | Stage #1: With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 25℃; for 2 h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water |
To a stirred solution of XII-3 (700 mg, 2.5 mmol) in 15 mL of MeOH/H2O/THF (v/v/v=1/1/1) was added lithium hydroxide monohydrate (1.05 mg, 25 mmol). After the addition, the solution was stirred at 25° C. for 2 h. The mixture was concentrated in vacuo and adjusted pH to 4 with HCl (1N). The aqueous phase was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to afford crude XII-4 (623.0 mg, crude yield 98percent), which was used to next step directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.77 g (76.6 mmol, 66%) | With sodium hydroxide; In diethyl ether; sodium carbonate; | Step 1. 1-Methyl-4-[(4-methylphenyl)amino]-1H-pyrazole-5-carboxylic acid A mixture of <strong>[75092-30-7]4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid</strong> ((Y. A. Manaev et al., J. Gen. Chem. USSR. (Engl. Transl.), 1982, 52, 2291), 2.92 g, 11.6 mmol), p-toluidine (6.20 g, 57.9 mmol), and copper powder (1.17 g, 18.4 mmol) in 5% aqueous sodium carbonate (60 ml) was stirring at 100 C. for 5 h. After cooling to room temperature, diethyl ether (100 ml) and 2N aqueous sodium hydroxide (100 ml) were added. This mixture was filtered through a pad of Celite, which was washed with 2N sodium hydroxide (200 ml) and ether (100 ml). The separated aqueous layer was washed with ether (100 ml), filtered through a pad of Celite again, and acidified with concentrated hydrochloric acid. The precipitate was collected by filtration, and washed with water to give 1.77 g (76.6 mmol, 66%) of the title compound as a gray powder. MS (EI) m/z: 231 (M+). 1H-NMR (DMSO-d6) delta: 7.61 (1 H, s), 7.05 (2 H, d, J=8.6 Hz), 6.98 (2 H, d, J=8.9 Hz), 4.00 (3 H, s), 2.22 (3 H, s). Two signals due to NH and CO2H were not observed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
282 mg (61%) | With sodium hydroxide; In diethyl ether; | Step 1. 4-[(4-Fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid A mixture of <strong>[75092-30-7]4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid</strong> ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 500 mg, 1.98 mmol), 4-fluoroaniline (0.94 ml, 9.90 mmol), copper powder (200 mg) and 5% aqueous sodium carbonate (10 ml) was stirred for 16 h at 100 C. After cooling to room temperature, 2N aqueous sodium hydroxide (100 ml) and diethyl ether (50 ml) were added to the mixture. The mixture was filtered through a pad of Celite. The water layer was separated, washed with diethyl ether (50 ml) and acidified with concentrated hydrochloric acid. The formed precipitate was collected by filtration and dried to give 282 mg (61%) of the title compound as a white solid. Rf value: 0.50 (methanol/dichloromethane/acetic acid=1/10/2 drops). 1H-NMR (DMSO-d6) delta: 7.60 (1 H, s), 7.09-7.05 (4 H, m), 4.01 (3 H, s). Two signals due to NH and CO2H were not observed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.86 g (50%) | In dimethyl sulfoxide; | Step 1. 4-[(4-Benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid A mixture of <strong>[75092-30-7]4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid</strong> ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 8.0 g, 31.74 mmol), 4-benzylaniline (21.03 g, 114.76 mmol) and copper powder (3.2 g) in a mixture of 5% aqueous sodium carbonate (160 ml) and dimethylsulfoxide (80 ml) was stirred for 17 h at 100 C. After cooling to room temperature, the mixture was filtered through a pad of Celite, which was washed with water, 2N aqueous sodium hydroxide and diethyl ether. The separated water layer was washed with diethyl ether (100 ml*2). The water layer was acidified with concentrated hydrochloric acid and the formed solid was collected by filtration, dried, to give 4.86 g (50%) of the pure title compound as a pale brown solid. Rf value: 0.50 (methanol/dichloromethane/acetic acid=1/10/2 drops). 1H-NMR (DMSO-d6) delta: 7.63 (1 H, s), 7.50 (1 H, br s), 7.31-6.96 (9 H, m), 4.00 (3 H, s), 3.85 (2 H, s). One signal was not observed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | PREPARATION 65(4-lodo-2-meth -2H-pyrazol-3-yl)methanolTo a solution of <strong>[75092-30-7]4-iodo-2-methyl-2H-pyrazole-3-carboxylic acid</strong> (1.0 g, 3.96 mmol) in tetrahydrofuran (10 mL), under an atmosphere of nitrogen, was added carbonyl diimidazole (0.78 g, 4.36 mmol, 1.1 eq.). The resulting mixture was stirred at room temperature for 1.5 hr before adding sodium borohydride (0.75 g, 19.8 mmol, 3.0 eq.) followed by a solution of methanol in tetrahydrofuran (5 mL), dropwise over a period of 10 min. The resulting mixture was stirred for 3hr before quenching with 2M aqueous hydrochloric acid (30 mL). This mixture was partition with ethyl acetate (50 mL). The organic phase was washed with 1 aqueous sodium hydrogen carbonate (20 mL), saturated brine (20 mL) and dried over sodium sulphate. The resulting mixture was filtered and the filtrate concentrated under reduced pressure to give the title compound as a brown oil (0.56 g, 60%). 1H N R (400 MHz, DMSO-d6) delta ppm 3.87 (s, 3 H) 4.48 (d, J=5.47 Hz, 2 H) 5.30 (t, 1 H) 7.42 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.5% | To a stirred solution of XII-3 (700 mg, 2.5 mmol) in 15 mL of MeOH/H2O/THF (v/v/v=1/1/1) was added lithium hydroxide monohydrate (1.05 mg, 25 mmol). After the addition, the solution was stirred at 25 C. for 2 h. The mixture was concentrated in vacuo and adjusted pH to 4 with HCl (1N). The aqueous phase was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to afford crude XII-4 (623.0 mg, crude yield 98%), which was used to next step directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.3 g | With diphenyl phosphoryl azide; triethylamine; In toluene; at 80℃; for 2h;Inert atmosphere; | The mixture of XII-4 (2.1 g, 8.3 mmol), XII-4A (1.2 g, 9.8 mmol), DPPA (2.7 g, 9.8 mmol) and TEA (1.68 g, 16.6 mmol) in toluene (20 mL) was stirred at 80 C. under nitrogen for 2 hrs. Then the mixture was washed with H2O, and extracted with EtOAc. The organics were combined, dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE: EA=3:1) to afford XII-5 (2.3 g, yield: 74.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 80℃; for 16h; | A suspension of Preparation 16 (50 mg, 0.0897 mmol), <strong>[75092-30-7]4-iodo-2-methyl-2H-pyrazole-3-carboxylic acid</strong> (MFCD00461121) (23 mg, 0.0897 mmol), CS2CO3 (58 mg, 0.179 mmol) and PdCl2(dppf)2.CH2Cl2 (4 mg, 0.00448 mmoL) in 1,4-dioxane (0.8 mL) and H2O (0.2 mL) was stirred at 80 C. for 16 h. LCMS showed the reaction was complete. The reaction was dried over Na2SO4 and filtered. The filtrate was concentrated to dryness and purified by prep-HPLC (petroleum ether:EtOAc, 1:1) to give the N-BOC intermediate (10 mg, 20%) as a white solid. The reaction was repeated to obtain additional material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | A round-bottom flash was charged with <strong>[75092-30-7]4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid</strong> (297 g, 1.18 mol), DCM (2.97 L), and 1,1?-carbonyldiimidazole (CDI) (207 g, 97% by mass, 1.24 mol). The reaction mixture was stirred at room temperature for 45 min. Ammonium chloride (189 g, 3.53 mol) and triethylamine (498 mL, 3.53 mol) were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was suspended in H2O (3 L) and granulated at room temperature for 1 h. The solid was collected via filtration, washed with H2O, and dried in a vacuum oven to afford 4-iodo-1-methyl-1H-pyrazole-5-carboxamide as a colorless solid (222 g, 75% yield). 1H NMR (CDCl3) delta: 7.53 (s, 1H), 6.56 (br s, 1H), 6.01 (br s, 1H), 4.21 (s, 3H). UPLC (UPLC-MS Method 1): tR=0.15 min. MS (ES+): 251.1 (M+H)+. | |
75% | A round-bottom flash was charged with 4-iodo-i -methyl-i H-pyrazole-5-carboxylic acid(297 g, i.i8 mol), DCM (2.97 L), and i,i?-carbonyldiimidazole (CDI) (207 g, 97% bymass, 1.24 mol). The reaction mixture was stirred at room temperature for 45 mm.Ammonium chloride (189 g, 3.53 mol) and triethylamine (498 mL, 3.53 mol) were addedand the reaction mixture was stirred at room temperature overnight. The reaction mixturewas concentrated in vacuo and the residue was suspended in H20 (-3 L) and granulated at room temperature for 1 h. The solid was collected via filtration, washed with H20, and dried in a vacuum oven to afford 4-iodo-i -methyl-i H-pyrazole-5-carboxamide as a colorless solid (222 g, 75% yield).1H NMR (CDCI3) O: 7.53 (5, 1 H), 6.56 (br s, 1 H), 6.01 (br s, 1 H), 4.21 (5, 3H). UPLC (UPLC-MS Method 1): tR = 0.15 mm.MS (ES+): 251.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid (301.68 g, 1.2 moles) was slurried in 1.2 L of DCM and DMF (2.3 g, 31 mmol) followed by addition of oxalyl chloride (115 mL, 1.3 moles) over 37 minutes and then stirred at room temperature for 3 h. To the resulting solution was added EtOH (750 mL, 12.9 mol) over 5 min followed by stirring at room temperature for 2 h. The crude product solution was concentrated to dryness in vacuo and then reconstituted in 1.2 L of warm heptane followed by filtration. The filtrate was concentrated by removing 500 mL of heptane, resulting in precipitation of solids. The solids were collected via filtration and dried to afford ethyl 4-iodo-1-methyl-1H-pyrazole-5-carboxylate as a white solid (297.6 g, 89% yield). 1H NMR (CDCl3) delta 7.57 (s, 1H), 4.43 (q, 2H), 4.21 (s, 3H), 1.47 (t, 3H). UPLC (UPLC Method 4): tR=5.10 min. MS (ES+) 280.9 (M+H |
Tags: 75092-30-7 synthesis path| 75092-30-7 SDS| 75092-30-7 COA| 75092-30-7 purity| 75092-30-7 application| 75092-30-7 NMR| 75092-30-7 COA| 75092-30-7 structure
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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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