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CAS No. : | 161798-02-3 | MDL No. : | MFCD15144699 |
Formula : | C14H12N2O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WTMZFYPEMMFHPR-UHFFFAOYSA-N |
M.W : | 288.32 | Pubchem ID : | 135627703 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.21 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 75.34 |
TPSA : | 111.45 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.59 cm/s |
Log Po/w (iLOGP) : | 2.64 |
Log Po/w (XLOGP3) : | 3.48 |
Log Po/w (WLOGP) : | 2.87 |
Log Po/w (MLOGP) : | 0.96 |
Log Po/w (SILICOS-IT) : | 3.9 |
Consensus Log Po/w : | 2.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.96 |
Solubility : | 0.0314 mg/ml ; 0.000109 mol/l |
Class : | Soluble |
Log S (Ali) : | -5.5 |
Solubility : | 0.000906 mg/ml ; 0.00000314 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.18 |
Solubility : | 0.0188 mg/ml ; 0.0000653 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.04 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
palladium-carbon; In tetrahydrofuran; ethanol; | Reference Preparation Example 17 Ethyl 2-[4-(benzyloxy)-3-cyanophenyl]-4-methyl-1,3-thiazole-5-carboxylate was suspended in a mixture of THF and ethanol, then palladium-carbon was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature to obtain ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate. APN: 287. | |
With hydrogen;palladium on activated charcoal; In tetrahydrofuran; ethanol; at 20℃; | Reference Example 8 Ethyl 2-[4-(benzyloxy)-3-cyanophenyl]-4-methyl-1,3-thiazole-5-carboxylate was suspended in a mixture of THF and ethanol, then palladium-carbon was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature to obtain ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate. APN: 287. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.2% | With potassium carbonate; potassium iodide; In ethyl acetate; at 65 - 70℃; for 5h; | The resulting solid compound input 360 ml ethyl acetate, 116g potassium carbonate, 3gKI and stirring and heating. T=65 °C, starting to drop the 116.5g bromo isobutane solution. Then completing, t=70 °C, thermal insulation 5h feed liquid cooling, t=15 °C, stirring 30min, filtering, adding water 120 ml beating 1.5h, filtering to obtain compound IV wet product. dries 88.6g yellow solid. Molar yield: 98.2percent, purity (HPLC): 98.7percent, shan Za (HPLC): 0.15percent, always mixed (HPLC): 1.3percent. |
92.9% | With potassium carbonate; In N,N-dimethyl-formamide; at 75℃; for 8h; | Example 4: Synthesis of Ethyl-2-(3-Cvano-4-Isobutyloxyphenyl)-4-Methyl-5-Thiazole CarboxylatePotassium carbonate (300 g, 2.17 mol) and isobutyl bromide (142.7 g, 1.041 mol) were added to a solution of ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate (100 g, 0.347 mol) in dimethylformamide (300 mL), and the reaction mixture was heated at a temperature of about 75°C for about 8 hours. After completion of reaction, the reaction mixture was cooled to about 40°C and water was added. The reaction mixture was further cooled to about 0°C and stirred for about 1 hour. The solid thus obtained was filtered, washed with water and dried to give title compound. (Yield: 11 lg, 92.9percent) |
88% | With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 90℃; for 3h; | Example - 3: Preparation of Ethyl 2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole -5-carboxylateA mixture of 10. Og of Ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole -5- carboxylate, 30 g of NMP, 9.6 g of potassium carbonate and 7.2 g of isobutyl bromide were stirred for 3 hours at 90°C. Reaction mass was diluted with 100 ml of purified water. The reaction mass was filtered and washed with purified water and ethanol to give 10.5 g of Ethyl-2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole -5-carboxyltae (yield 88.0percent). |
88.0% | With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 90℃; for 3h; | Example-3 Preparation of Ethyl 2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole-5-carboxylate A mixture of 10.0 g of Ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate, 30 g of NMP, 9.6 g of potassium carbonate and 7.2 g of isobutyl bromide were stirred for 3 hours at 90° C. Reaction mass was diluted with 100 ml of purified water. The reaction mass was filtered and washed with purified water and ethanol to give 10.5 g of Ethyl-2-(3-cyano-4-isobutoxy phenyl)-4-methyl thiozole-5-carboxylate (yield 88.0percent). |
2.28 g | With potassium carbonate; In N,N-dimethyl-formamide; at 75℃; for 15h; | Dissolve 2.2 g of <strong>[161798-02-3]ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate</strong> (Formula VI) in 7 ml dimethylformamide and to this mixture add 6.6 g of potassium carbonate and 3.14 g of isobutyl bromide. Stir the reaction at 75 °C for 15 hours and then cool to 40 °C. Add 15 ml process water and cool to 0-5 °C. Filter the precipitated solid off and wash with 15 ml process water, which, after drying, affords 2.28 g of ethyl 2-(3-cyano-4-isobutoxyphenyl)-4- methylthiazole-5-carboxylate (Formula Illb). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Example - 2: Preparation of Ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl thiozole - 5-carboxylateA mixture of 10. Og of Ethyl-2-(3-formyl-4-hydroxy phenyl)-4-methyl thiozole -5- carboxylate and 2.85 g of hydroxylamine hydrochloride were stirred for 30 minutes in 30 g of Dimethylformamide. To this reaction mixture 3.3 grams of acetyl chloride was added and stirred at 90°C for 2-3 hours. Reaction mass was cooled to room temperature and diluted with 100 ml of water and stir for 2 hours. The reaction mass was filtered and washed with purified water to give 10.0 g of Ethyl-2-(3-cyano-4-hydroxy phenyl)-4- methyl thiozole -5-carboxyltae (yield 99.0percent). | |
99.0% | Example-2 Preparation of Ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl thiozole-5-carboxylate A mixture of 10.0 g of Ethyl-2-(3-formyl-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate and 2.85 g of hydroxylamine hydrochloride were stirred for 30 minutes in 30 g of Dimethylformamide. To this reaction mixture 3.3 grams of acetyl chloride was added and stirred at 90° C. for 2-3 hours. Reaction mass was cooled to room temperature and diluted with 100 ml of water and stir for 2 hours. The reaction mass was filtered and washed with purified water to give 10.0 g of Ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate (yield 99.0percent). | |
97.6% | With formic acid; hydroxylamine hydrochloride; sodium acetate; at 100 - 105℃; for 10h; | In a 1 L four-necked flask, 60 g of a non-Bustam aldehyde substrate, 866.7 g of anhydrous formic acid, 17.3 g of hydroxylamine hydrochloride and24g anhydrous sodium acetate, stirring warming. The temperature of T = 100 ~ 105 , heat stirring 10h, the material vacuum distillation to no distillate to get the powdery solid compound . Weighing 86.8g, molar yield 97.6percent, purity (HPLC): 98.9percent, single impurity (HPLC): 0.22percent, total miscellaneous (HPLC): 1.1percent. |
85.9% | With formic acid; hydroxylamine hydrochloride; sodium formate; at 100℃; for 8h; | Example 3: Synthesis of ethyl-2-(3-cyano-4-hvdroxyphenvn-4-methyl-5-thiazole carboxylateHydroxylamine hydrochloride (35.82 g, 0.515 mol) and sodium formate (46.73 g, 0.687 mol) were added to a solution of ethyl-2-(3-formyl-4-hydroxyphenyl)-4-methyl-5- thiazole carboxylate (100 g, 0.343 mol) in formic acid (anhydrous, 300 mL) and the reaction mixture was heated to a temperature of about 100°C for about 8 hours. After completion of reaction, the reaction mixture was cooled to about 40°C and water was added to it. The reaction mixture was cooled to about 25°C and stirred for about 1 hour. The solid obtained was filtered, washed with water and dried. The solid was then dissolved in acetone at about 50°C and water was added slowly over a period of about 30 minutes. The mixture was cooled to about 25°C and again stirred for about 1 hour. The solid thus obtained was filtered, washed with acetone:water (1 :1) mixture and dried to obtain the title product. (Yield: 85 g, 85.9percent) |
42.6% | With ammonia; iodine; In tetrahydrofuran; water; at 25 - 30℃; | In a 50 mL round-bottomed flask charge under stirring 0.5g (1.72 mmol) of ethyl 2-(3-formyl-4- hydroxyphenyl)-4-methylthiazole-5-carboxylate in 8.6 mL THF, at 25-30 °C. Add 10.3 mL (544.94 mmol) 25percent aqueous ammonia, under stirring at 25-30 °C. Add 480 mg (1.89 mmol) iodine (I2) to the reaction mass, stir the reaction mixture at 25-30 °C for 15-30 min. Check the progress of the reaction by TLC (cyclohexane: ethyl acetate 1 :1). Starting material is consumed. Add 8.6 mL 5percent w/v aqueous thiosulfate and 40 mL ethyl acetate at the reaction mass, separate organic layer and extract aqueous layer twice with 40 mL ethyl acetate. Combine organic layers, dry over anhydrous sodium sulfate, filter off and concentrate to dryness. Purification of the residue with column chromatography (cyclohexane: ethyl acetate 3: 1) afforded 0.213 g of ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate (Formula Ilia). Yield : 42.6percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With sodium dihydrogenphosphate; potassium carbonate; In water; acetonitrile; at 150℃; for 12h;Sealed tube; | A solution of compound A (0.50 g, 1.734 mmol), 2,2-dimethyloxirane (1.25 g, 17.34 mmol), K2CO3 (0.24 g, 1.734mmol) and NaH2PO4 (0.21 g, 1.734 mmol) in CH3CN (40mL) and H2O (10 mL) was warned up to 150 C in a sealed tube for 12 h. Then the mixture was cooled to room temperature, diluted with H2O (60 mL) and extracted with EtOAc(30 mL ). The combined organic layers were washed with H2O (20 mL ) and brine (50 mL ), dried over anhydrous Na2SO4, filtered and evaporated to dryness. Flash chromatography on silica gel (petroleum ether/EtOAc) couldafford 9 (0.30 g, 48%) as colorless solid.9: mp 180-184 C, 1H NMR (400 MHz, CDCl3, ppm):1.42-1.37 (m, 9H, C(CH3)2 and CH2CH3), 2.78 (s, 3H,ArCH3), 3.97 (s, 2H, ArOCH2), 4.36 (q, J = 7.2 Hz, 2H,CH3CH2), 7.05 (d, J = 8.8 Hz, 1H, ArH), 8.14 (d, J = 8.8 Hz,1H, ArH), 8.20 (s, 1H, ArH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | To a solution of compound A (0.60 g, 2.08 mmol) in 15mL DMF was added K2CO3 (1.44 g, 10.41 mmol) and KI(0.17 g, 1.04 mol). After the mixture was activated at 80 Cfor 30 min, compound 7 (0.96 g, 6.24 mmol) was slowly added and maintained at 80 C for another 4 h. The mixturewas cooled to room temperature, treated with H2O (75 mL),and extracted with EtOAc (35 mL ). The combined organiclayers were washed with H2O (35 mL ) and brine, dried over anhydrous Na2SO4, filtered and evaporated todryness. The residue was crystalized in a mixture of EtOAc:hexane = 1: 2 to afford 8 (0.47 g, 63%) as yellow ctystals.8: mp 195-198 C, 1H NMR (400 MHz, CDCl3, ppm):1.13 (d, J = 6.8 Hz, 3H, CHCH3), 1.39 (t, 2H, J = 7.2 Hz,3H, OCH2CH3), 1.85 (br, 1H, OH), 2.28 (m, 1H, CH), 2.78(s, 3H, ArCH3), 3.77 (m, 2H, HOCH2), 4.14 (m, 2H,ArOCH2), 4.36 (q, J = 7.2 Hz, 2H, COOCH2), 7.08 (d, J =8.8 Hz, 1H, ArH), 8.13 (dd, J = 2.4, 8.8 Hz 1H, ArH), 8.18(d, J = 2.4 Hz, 1H, ArH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.69 g | With sodium chlorite; In ethanol; for 2h;Inert atmosphere; Green chemistry; | A solution of 1q (1.00 g, 3.4 mmol) and NH4OAc (0.54 g, 6.8 mmol) in ethanol (15 mL) was stirred for 30 min at 50 C. NaClO2 (80%,0.62 g, 5.4 mmol) was then added and the mixture was stirred for 2h under nitrogen (TLC control, petroleum ether [boiling range:60-90 C)/EtOAc (3:1, v/v)]. After cooling, the filtrate was rotary evaporated to dryness and the residues were purified by column chromatography on silica gel (ethyl acetate/n-hexane, 1:8) to afford 2q? [yield 0.69 g (70%)]. Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate (2q?): Pale yellow solid; m.p. 184.5-185.5 C (lit.11 184.7-185.4 C);1H NMR (600 MHz, DMSO): delta 11.89 (s, 1H), 8.15 (d, J = 2.4 Hz, 1H),8.05 (dd, J1 = 2.4 Hz, J2 = 4.2 Hz, 1H), 7.11-7.09 (m, 1H), 4.27 (q, J =7.2 Hz, 2H), 2.63 (s, 3H), 1.30 (t, J = 7.2 Hz, 3H); 13C NMR (150 MHz,DMSO): delta 167.5, 162.9, 161.7, 160.5, 133.3, 131.9, 124.3, 121.3, 117.4,116.4, 100.3, 61.6, 17.6, 14.6; MS (ESI): 289.1 [M + H]+ (lit.11 MS (ESI):286.9 [M - H]-). |
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