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CAS No. : | 70817-26-4 | MDL No. : | MFCD00159595 |
Formula : | C10H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UCPVQFRIXFGLOJ-UHFFFAOYSA-N |
M.W : | 174.20 | Pubchem ID : | 822983 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.69 |
TPSA : | 38.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.65 cm/s |
Log Po/w (iLOGP) : | 1.81 |
Log Po/w (XLOGP3) : | 1.01 |
Log Po/w (WLOGP) : | 1.21 |
Log Po/w (MLOGP) : | 1.15 |
Log Po/w (SILICOS-IT) : | 1.36 |
Consensus Log Po/w : | 1.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.05 |
Solubility : | 1.55 mg/ml ; 0.0089 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.4 |
Solubility : | 6.96 mg/ml ; 0.04 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.75 |
Solubility : | 0.308 mg/ml ; 0.00177 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.56 |
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 |
---|---|---|
88% | With sodium tetrahydroborate; In ethanol;Cooling with ice; | 3) The 1.72 g (0.01 muM) 1 - phenyl -4 - pyrazole formaldehyde in 100 ml of the single port in the bottle, by adding 35 ml of ethanol, stirring in ice bath, is added in batches to the 0.95 g (0.025 muM) of the sodium borohydride, TLC monitoring after the reaction, reducing pressure and solvent, adding (3 × 50 ml) ethyl acetate extraction, the organic phase with saturated salt water 50 ml washing, desolvation residue after column chromatography (eluting agent is ethyl acetate with petroleum ether (reflux 60 - 90 C), the volume ratio of 1:4) shall be 1.53 g white solid, yield 88.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; zinc(II) chloride; Petroleum ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With borane-THF; In tetrahydrofuran; at 20℃; | [00240j To a solution of <strong>[1134-50-5]1-phenyl-1H-pyrazole-4-carboxylic acid</strong> (590 mg, 3.1 mmol) in THF (6.9 mL) at rt was added borane-THF complex (6.2 mL, 6.2 mmol, 1 M in THF), and the reaction mixture was stirred over night. The mixture was quenched by the slowaddition of 1M NaOH and pouring into water. The mixture was extracted with ether (2x). The combined organics were washed with water and brine, dried over Na2SO4, andconcentrated to give Example 22A a white solid. MS (ESI) m/z 175.1 (M+H). The crude product was used in the next synthetic step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphoric acid; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide; acetic acid for 15h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With lithium aluminium tetrahydride In diethyl ether for 7h; Heating; | |
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; | 1-0 In a round bottom flask substituted with argon, the compound 5 was added to anhydrous tetrahydrofuran, and the solution was cooled to 0°C. Lithium aluminum hydride (2.5M solution of tetrahydrofuran, 1.5eq) was slowly added to reaction solution, followed by stirring at 0°C for one hour. After completion of the reaction, diethyl ether, distilled water and 15% (wt%) aqueous sodium hydroxide solution were added to terminate the reaction, and the resulting suspension was filtered and concentrated under reduced pressure to synthesize compound 6 of Reaction Formula 3. Without further purification, it was used in further reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 48percent hydrobromic acid, acetic acid / 15 h / Heating 2: dimethylsulfoxide / 0.17 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 48percent hydrobromic acid, acetic acid / 15 h / Heating 2: dimethylsulfoxide / 0.17 h / Ambient temperature 3: 95 percent / aq. KOH / ethanol / 10 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 59 percent / acetic acid / ethanol / 2 h / Heating 2: 94 percent / LiAlH4 / diethyl ether / 7 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid 2: aqueous K2CO3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ZnCl2; petroleum ether / unter Einleiten von HCl und konz. H2SO4 2: acetic acid 3: aqueous K2CO3 | ||
Multi-step reaction with 2 steps 1: phosphorus trichloride / 100 °C 2: sodium tetrahydroborate / ethanol / Cooling with ice | ||
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 12 h / 90 °C 2: sodium tetrahydroborate / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 200 °C 2: ZnCl2; petroleum ether / unter Einleiten von HCl und konz. H2SO4 3: acetic acid 4: aqueous K2CO3 | ||
Multi-step reaction with 2 steps 1.1: sodium hydroxide / dichloromethane; water / 0.17 h / Schlenk technique; Inert atmosphere; Green chemistry 1.2: 255 / 2 h / 110 °C / Schlenk technique; Green chemistry 2.1: lithium aluminium tetrahydride / tetrahydrofuran-d8 / 0 - 20 °C / Inert atmosphere; Schlenk technique | ||
Multi-step reaction with 2 steps 1: montmorillonite K10 Clay / neat (no solvent) / 15 h / 65 °C / Inert atmosphere; Sealed tube 2: lithium aluminium tetrahydride / tetrahydrofuran-d8 / 0 - 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With thionyl chloride In dichloromethane Cooling with ice; | 2.4 4) Will be 1.74 g (0.01 µM) 1 - phenyl -4 - hydroxymethyl pyrazole, in 100 ml of the single port in the bottle, by adding 35 ml dichloromethane, stirring in ice bath, dripping 1.43 g (0.012 µM) of thionyl chloride, device end gas collecting device, TLC monitoring after the reaction, reducing pressure and solvent, adding (3 × 50 ml) ethyl acetate extraction, the organic phase with saturated salt water 50 ml washing, desolvation residue after column chromatography (eluting agent is ethyl acetate with petroleum ether (reflux 60 - 90 °C), the volume ratio of 1:4) shall be 1.55 g brown solid, yield 81.0%. |
With thionyl chloride In dichloromethane at 20℃; for 1h; | 9.a (1 -Phenyl- lH-pyrazol-4-yl)~methanol (2 g) in dichloromethane (15 mL) was treated with thionyl chloride (10 mL) and the mixture stirred at 200C for Ih. The resulting suspension was diluted with wøhexane (15 mL) and the solid collected by filtration to afford the subtitled compound as an off-white solid (1.120 g).1H NMR (400 MHz, CDCl3) Î' 8.61 (IH, s), 7.84 - 7.80 (3H, m), 7.53 - 7.47 (2H, m), 7.35 7.30 (IH, m), 4.77 (2H, s). | |
With thionyl chloride In dichloromethane at 20℃; for 1h; | 14.a Example 14: (R)-3-(l-Phenyl-cycloheptanecarbonyloxy)-l-(l-phenyl-lH-pyrazol-4- ylmethyl)-l-azonia-bicyclo[2.2.2]octane chloridea) 4-Chloromethyl- 1 -phenyl- lH-pyrazole (1 -Phenyl- lH-pyrazol-4-yl)-methanol (2 g) in dichloromethane (15 mL) was treated with thionyl chloride (10 mL) and the mixture stirred at 200C for 1 h. The resulting suspension was diluted with z'søhexane (15 mL) and the solid collected by filtration (1.12 g).1H NMR (399.826 MHz, DMSO-D6) δ 8.61 (s, IH), 7.84 - 7.80 (m, 3H), 7.53 - 7.47 (m, 2H), 7.35 - 7.30 (m, IH), 4.77 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2.08 h / 0 - 20 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: potassium fluoride; copper(l) iodide; methyl bromodifluoroacetate; potassium iodide / N,N-dimethyl-formamide; acetonitrile / 24 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With catalyst Silica-2 (4.02percent Cu) In 1,2-dichloro-benzene at 140℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / Cooling with ice 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / 20 °C 2: acetonitrile / 0.05 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / 20 °C 2: acetonitrile / 2191.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium fluoride; copper(l) iodide; methyl bromodifluoroacetate; potassium iodide In N,N-dimethyl-formamide; acetonitrile at 40 - 70℃; for 24.5h; Inert atmosphere; Sealed tube; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With lithium aluminium tetrahydride In tetrahydrofuran-d8 at 0 - 20℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 2 h / 75 °C 2: trifluoroacetic acid / 12 h / 90 °C 3: sodium tetrahydroborate / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With formic acid In chloroform at 65℃; for 8h; | Synthesis of 2,6-di-tert-butyl-4-((1-phenyl-1H-pyrazol-4-yl)methyl)phenol (3) (LQFM219) [10]: To a heated heterogeneous mixture offformic acid (3 mL), 1-phenyl-1H-pyrazol-4-yl)methanol (7) (172 mg,1 mmol), 2,6-di-tert-butylphenol (8) (206 mg, 1.00 mmol), and 2 mL ofCHCl3 were added, and the mixture was heated at 65 °C for 8 h. At theend of the reaction, the residue was split between water and CH2Cl2.The spelling formed was precipitate was filtered off under vacuum anddried. The phases were separated, the aqueous layer was extracted 3 × 15 mL with CH2Cl2, and the combined organic layers were driedwith sodium sulphate and concentrated in vacuo. The crude product wascrystallised from (MeOH/H2O = 1:9) to 2,6-di-tert-butyl-4-((1-phenyl-1H-pyrazol-4-yl)methyl)phenol (3) (181 mg, 50%) as a beige solid(m.p. = 122-124 °C, Rf = 0.60 [hexene/AcOEt = 7:3]). IRmax (KBr)cm-1: 3630 ( O-H); 3093 ( C-H); 2916 ( C-H); 1599 ( C = C); and752 ( Ar-1,4) (Fig. S1, Supplementary material); 1H NMR(500.13 MHz) CDCl3 (W): 7.57 (brs, H3); 7.68 (brd, J = 0.7 Hz, H5);3.81 (s, H6); 7.65 (dd, J = 8.5; 1.2 Hz, H2X); 7.42 (ddd, J = 8.5; 7.5;1.0 Hz, H3X); 7.24 (tt, J = 7.5; 1.2 Hz, H4X); 7.42 (ddd, J = 8.5; 7.5;1.0 Hz, H5X); 7.65 (dd, J = 8.5; 1.2 Hz, H6X); 7.05 (s, H3Y); 7.05 (s,H5Y); 1.43 (s, H8Y); 5.08 (s, OH) (Fig. S2 and Table 2, Supplementarymaterial); 2D NMR (HSQC/HMBC-125.76 MHz) CDCl3/TMS (W): 141.3(C-3); 123.8 (C-4); 125.4 (C-5); 30.4 (C-6); 140.4 (C-1X); 118.7 (C-2X);129.4 (C-3X); 126.0 (C-4X); 129.4 (C-5X); 118.7 (C-6X); 152.3 (C-1Y);136.1 (C-2Y); 125.0 (C-3Y); 131.1 (C-4Y); 125.0 (C-5Y); 136.1 (C-6Y);34.6 (C-7Y); 30.4 (C-8Y) (Figs. S3, S4; Table 2; Supplementary material);[M + H]+m/z of 363.2385 (Fig. S5, Supplementary material). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate / toluene / 2 h / 110 °C / Microwave irradiation 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h; | 1-0 Compound 6 was added to pyridinium chlorochromate (3eq) in dichloromethane solution, followed by stirring for 2 hours at room temperature. After completion of the reaction, a large amount of diethyl ether was added to the reaction suspension, followed by filtering. The obtained filtrate was concentrated under reduced pressure and the concentrate was purified through column chromatography (eluent: ethyl acetate/hexane (1:1) mixture) to obtain compound 3 of Reaction Formula 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 2: sodium acetate / ethanol / 15 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 2: sodium acetate / ethanol / 15 h / 60 °C 3: potassium hydroxide / methanol / 1.5 h / 60 °C |
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