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CAS No. : | 37052-78-1 | MDL No. : | MFCD00134581 |
Formula : | C8H8N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KOFBRZWVWJCLGM-UHFFFAOYSA-N |
M.W : | 180.23 | Pubchem ID : | 665603 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.84 |
TPSA : | 76.71 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 1.59 |
Log Po/w (XLOGP3) : | 1.4 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 0.97 |
Log Po/w (SILICOS-IT) : | 2.26 |
Consensus Log Po/w : | 1.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.33 |
Solubility : | 0.846 mg/ml ; 0.00469 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.61 |
Solubility : | 0.437 mg/ml ; 0.00243 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.15 |
Solubility : | 0.128 mg/ml ; 0.000711 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
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 |
---|---|---|
63% | With potassium hydroxide In CS2; ethanol; water | EXAMPLE 4 2-[(3,7-Dimethyl-2,6(E)-octadienyl)thio]-5-methoxy-1H-1,3-benzimidazole Monooxalate To potassium hydroxide (3.8 g, 0.067M) in ethanol (20 mL) and water (7 mL) was added 2.5 mL CS2 (3.09 g, 0.04M) (H2 S trapped over clorox). The reaction mixture was stirred for 30 minutes at ambient temperature, cooled to 0° C., and 4-methoxy-o-phenylene diamine (5.23 g, 0.03M) was slowly added. This reaction mixture was then stirred at reflux for 4 hours, stirred at ambient temperature overnight (basic soln. with pH paper), evaporated in vacuo and diluted with CH2 Cl2. Addition of water gave a precipitate which was suspended in CH2 Cl2 and acidified to pH 4. Filtration of the suspension gave purple crystalline 5-methoxy-2-mercaptobenzimidazole (3.4 g, 63percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With tetrabutylammomium bromide; edetate disodium; sodium hydroxide In dichloromethane; water | Step S1: 80.0 g (0.36 mol) of 4-methoxy-3,5-dimethyl-2-chloromethylpyridine hydrochloride (Compound I) was added to 480 mL of dichloromethane.0.2 g of disodium edetate was dissolved in 80 mL of water and added to the reaction solution.Step S2: After stirring and dissolving, 64.0 g (0.356 mol) was added.2-mercapto-5-methoxybenzimidazole (formula II),2.0 g (0.006 mol, 2percent molar equivalent) of tetrabutylammonium bromide,Sodium hydroxide adjusts the pH to 10,Stir until the reaction is over,Liquid separation,extraction,washing,dry,concentrate,a compound of formula III,Calculated in 100percent yield.Sodium hydroxide adjusts the pH to 10,The specific adjustment method is:Adjust the pH value in sections,Fine-tuning with 10percent sodium hydroxide in the early stage of the reaction;In the middle of the reaction, it was adjusted by using 15percent sodium hydroxide.Let it reach a pH of 8,Add 15percent sodium hydroxide every 10 minutes.This kind of benefit is adjusted more fully,Can better observe the effect of the adjustment,Make its PH reach 9;In the later part of the reaction, it was adjusted by using 20percent hydrogen peroxide.Make it PH to 10,The way the adjustment is added when it is interrupted,Add sodium hydroxide every 20 minutes;By adjusting the pH value in sections,Thereby making the adjusted pH more precise,More saving on sodium hydroxide,Save the production costs of the enterprise. |
95.2% | With sodium hydroxide In methanol; waterReflux | To a 1000 ml three-mouth flask is added 2-mercapto-5-methoxy benzimidazole 50.0g (0.28 µM), 500 ml of water and sodium hydroxide 22g (0.56 µM), after stirring dissolves clear slowly dropping 2-(chloromethyl)-4-methoxy-3,5-dimethyl pyridine hydrochloride 62g (0.28 µM) with methanol 300 ml of solution, stirring and heating to reflux the reaction, TLC monitoring raw material the reaction is complete. By reducing pressure methanol, water 200 ml, and dichloromethane is used for 300 ml * 3 extraction, the combined organic phase into the 2500 ml single-port in the bottle, the pressure off the solvent, adding petroleum ether to the residue in 1000 ml, lowering the temperature to 5 - 10 °C stirring crystallization, extraction, drying, to obtain white solid the ufiprazole 87g, yield 95.2percent. |
94% | With sodium hydroxide In ethanol; acetone at 40 - 45℃; for 3 h; Large scale | The reactor was added anhydrous ethanol 12.0kg, stirring, adding sodium hydroxide 1.09kg (27.25mol, 2.05eq) After stirring for 30 min, the internal temperature was controlled at 20-25 ° C. 2.40 kg (13.32 mol, 1.00 eq) of EL2,EL3 3.10kg (13.96mol, 1.05eq), acetone 4.0kg, the reaction was heated to an internal temperature of 40 ~ 45 ,Reaction 3h, TLC monitoring EL2 disappeared, the reaction was complete. The reaction liquid temperature was lowered to 25 ~ 30 ,After stirring for 30 min, insoluble materials were removed by filtration, the filter cake was washed once with 1.5 kg of acetone,The filtrate was concentrated under reduced pressure (bath temperature 40 ~ 45 ), the residue was added ethyl acetate 13.2kg, cooled to 0 ~ 5 ,Stir 3h, filter. The filter cake was washed once with 1.5 kg of ethyl acetate at 0-10 ° C,40 ~ 45 vacuum drying 8 to 10 hours. 4.14 kg of Intermediate 1 (EL1) was obtained with a yield of 94percent and a purity of 95.5percent by HPLC. |
94% | With sodium hydroxide In ethanol; acetone at 20 - 45℃; for 3 h; Large scale | The reactor was filled with 12.0 kg of absolute ethanol.Stir and add 1.09 kg of sodium hydroxide (27.25 mol, 2.05 eq). After stirring for 30 minutes, the internal temperature is controlled at 20 to 25°C.EL2 2.40 kg (13.32 mol, 1.00 eq) and EL3 3.10 kg (13.96 mol, 1.05 eq) were successively added.Acetone 4.0kg, the reaction solution was heated to an internal temperature of 40 to 45°C, and the reaction was conducted for 3 hours. TLC monitored EL2 disappeared. The reaction is complete. The internal temperature of the reaction solution is reduced to 25 to 30°C.After stirring for 30 minutes, the insoluble material was removed by filtration.The filter cake was washed once with acetone 1.5 kg, and the filtrate was concentrated under reduced pressure (bath temperature 40-45°C).The residue was added with 13.2 kg of ethyl acetate and cooled down to 0-5°C.Stir for 3h and filter. The filter cake was washed once with ethyl acetate of 0-10 °C 1.5 kg,40 ~ 45 °C vacuum drying 8 ~ 10 hours. Obtained 4.14 kg of Intermediate 1 (EL1) in 94percent yield.Purity was 95.5percent by HPLC. |
90% | With sodium carbonate In methanolReflux | Methanol was stirred at 25-35 0C and cooled to 20-25 0C. To the cold solution, 2-chloromethyl-3,5-dimethyl-4-methoxy-pyridine hydrochloride (1 mol), 2-mercapto-5-methoxy-benzimidazole (1 mol) and sodium carbonate (2.2 mol) and heated to reflux temperature. After completion of the reaction, the by-product formed was removed by filtration. Methanol was removed by distillation from the filtrate until small amount of methanol remains. The residue was dissolved in toluene and washed with aqueous solution of sodium carbonate. The organic layer was distilled under vacuum and cooled. To the residue toluene was added and seeded with qualified compound of formula (II). The obtained solid was filtered, washed with toluene and dried to obtain title compound. Yield: 80-90 percent; Purity: 99percent. |
130 g | With sodium hydroxide In methanol; water at 30 - 35℃; | 2-mercapto-5-methoxy benzimidazole (83.10 gm) was added at 30-35°C to a solution of NaOH (42 gm) in Methanol (200 ml) and Water (100 ml) to form a 1st reaction mass. A solution of 2-Chloromethyl-3,5-dimethyl-4-methoxy pyridine hydrochloride ( 100 gm) in methanol (50 ml) and water (150 ml) mixture was added to the 1st reaction mass in 90- 120 min at 30-35°C and the reaction mass stirred for 10-15 hrs and the reaction followed by TLC and HPLC.The reaction mass was worked up by addition of Water(900 ml), stirred for 2 hours, and filtered, washed with water(2x300 ml); suck dried, filtered and dried at 42-46C for 24-30 hrs in an oven to afford stage- 1 intermediate with M./C content < 0.5percent and a Dry Wt: - 130 gm |
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