Home Cart 0 Sign in  

[ CAS No. 1221722-10-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1221722-10-6
Chemical Structure| 1221722-10-6
Structure of 1221722-10-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1221722-10-6 ]

Related Doc. of [ 1221722-10-6 ]

Alternatived Products of [ 1221722-10-6 ]

Product Details of [ 1221722-10-6 ]

CAS No. :1221722-10-6 MDL No. :MFCD18322428
Formula : C15H11F3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :LNRROOUNLXDADK-UHFFFAOYSA-N
M.W : 296.24 Pubchem ID :53228253
Synonyms :

Calculated chemistry of [ 1221722-10-6 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 70.49
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 4.62
Log Po/w (WLOGP) : 5.52
Log Po/w (MLOGP) : 3.43
Log Po/w (SILICOS-IT) : 3.96
Consensus Log Po/w : 3.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.75
Solubility : 0.00531 mg/ml ; 0.0000179 mol/l
Class : Moderately soluble
Log S (Ali) : -5.32
Solubility : 0.00141 mg/ml ; 0.00000476 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.29
Solubility : 0.00151 mg/ml ; 0.00000509 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 1221722-10-6 ]

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:

Application In Synthesis of [ 1221722-10-6 ]

* 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.

  • Downstream synthetic route of [ 1221722-10-6 ]

[ 1221722-10-6 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 7697-26-9 ]
  • [ 139301-27-2 ]
  • [ 1221722-10-6 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate In 1,2-dimethoxyethane
  • 2
  • (2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine [ No CAS ]
  • 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid [ No CAS ]
  • [ 956697-53-3 ]
YieldReaction ConditionsOperation in experiment
93.6% In a 500 ml four-necked flask equipped with a stirring, thermometer, reflux condenser and exhaust gas absorption device,Add 250 g of 1,2-dichloroethane, 31.5 g (0.11 mol) of 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxylic acid (VI) ,0.05 g of DMF, 17.9 g (0.15 mol) of thionyl chloride, stirred at 55-60 C for 4 hours.Excess chlorosulfoxide and solvent were recovered by distillation under reduced pressure, and the residue acid chloride was dissolved in 100 g of fresh 1,2-dichloroethane (acid chloride solution) and transferred to a constant pressure dropping funnel.In a 500 ml four-necked flask with stirring, thermometer, reflux condenser and exhaust gas absorption device,Add 200 grams of 1,2-dichloroethane,15.2 g (0.11 mol) potassium carbonate, 20.7 g (0.1 mol) of (2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine (V) obtained by the method of Example 5. ),The solution of the acid chloride obtained above was added dropwise at 40-45 C for 2 hours, and then stirred at 45-50 C for 4 hours.The mixture was cooled to 20-25 C, filtered, and the filter cake was washed twice with 1,2-dichloroethane, 50 g each time, and the filtrate was combined. The filtrate was washed twice with saturated aqueous sodium chloride solution, 30 g each time. The organic phase is separated, and the organic phase is distilled under reduced pressure to recover the solvent.To the residue was added 0.5 g of activated carbon, 200 g of isopropanol, and decolorized at 80-82 C for 1 hour.
  • 3
  • 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid [ No CAS ]
  • [ 63700-19-6 ]
  • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carbonyl)oxy)tetrahydro-2H-pyran-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
265 mg With magnesium chloride; In dimethyl sulfoxide; at 37.0℃; for 8.0h;Enzymatic reaction; Example 10: Preparation of (2S,3S,4S,5i?,6S)-3,4,5-Trihydroxy-6-((2-methyl-4'- (trifluoromethoxy)-[1,1'-biphenyl]-3 carbonyl)oxy)tetrahydro-2H-pyran-2-carboxylic acid (metabolite m47e) 2-methyl-4'-(trifIuoromethoxy)-[1 , 1 '-biphenyj-3-carboxyic acid<strong>[63700-19-6]UDPGA</strong>dog liver homogenatePreparation of dog liver homogenate: 100 g of frozen dog liver were defrosted and cut into small pieces. After addition of one volume equivalent of ice cold 0.9 % NaCl solution and mixing in a Dispomix blender (VWR International, Dietikon, Switzerland), the tissue was homogenized in a "Potter S" Tissue Homogenizer (Braun Biotech Inc., Melsungen, Germany) under cooling in ice water at 100 % stirrer speed. The homogenate was centrifuged at 4 - 6 C for 30 min at 10,000 rpm (= 17,000 x g) in a Beckmann Coulter centrifuge (Fullerton, CA, USA) type Avanti J-HC equipped with a JA-10 rotor. The supernatant served as the enzyme source.Preparative biotransformation: 32 mL of 1 M MES buffer (2-(N- morpholino)ethanesulfonic acid, pH 6.0), was mixed with 40 mL of a uridine 5'-diphospho- glucuronic acid trisodium salt solution (<strong>[63700-19-6]UDPGA</strong>, 200 mM in 20 mM HEPES buffer (4-(2- hydroxyethyl)-l-piperazineethanesulfonic acid), pH 7.5), 10 mL of a solution of 2-methyl-4'- (trifluoromethoxy)-[l,l'-biphenyl]-3-carboxylic acid (100 mM in DMSO), 40 mL of a MgCl2- solution (100 mM in water) and 100 mL of dog liver S9-preparation. The mixture was incubated at 37C and 180 rpm for 8 h. Then it was acidified with 2 mL of formic acid and stored frozen until purification of the glucuronide.The reaction mixture was defrosted, extracted by mixing with 400 mL of isopropanol for one hour and centrifuged. The supernatant was filtered and adsorbed on the column by premixing it with 9 volumes of the aqueous mobile phase with the aid of 2 pumps pumping at a flow ratio of 10 : 90. The acylglucuonide was purified by two RP-18 liquid chromatography runs using a gradient from 10 to 100 % B (v/v) of methanol as mobile phase B and a 0.05 % ammonium formate solution as mobile phase A. The solvent was removed from the product containing fractions in a rotary evaporator and subsequent by lyophilization. 265 mg of acylglucuronide with a purity of > 99 % (LC/fullDAD) was obtained.LC/MS (m/z, [M + NH4+]): 490.11H NMR (600 MHz, DMSO-i/6): δ ppm 2.34 (s, 3H), 3.34 (t, 1H), 3.38 (t, 1H), 3.42 (t, 1H), 3.85 (d, 1H), 5.64 (d, 1H), 7.38 - 7.5 (m, 6H), 7.89 (d, 1H)
  • 4
  • [ 76006-33-2 ]
  • [ 139301-27-2 ]
  • [ 1221722-10-6 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 130℃; for 12h; Inert atmosphere; 6.1 (1) Synthesis of compound I: Under nitrogen, 3-bromo-2-methylbenzoic acid (1.0mmol), 4-(trifluoromethoxy)phenylboronic acid (2.0mmol), sodium carbonate (4.0mmol), Pd(PPh3)4 (0.05mmol) ), 4mL DME, 1mL water mixed, and reacted at 130°C for 12h. After the reaction was completed, it was diluted with water, extracted with ethyl acetate for 3 times, spin-dried under reduced pressure, dried over anhydrous sodium sulfate, and subjected to silica gel column chromatography to obtain a white solid with a yield of 90% (266.3 mg).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 130℃; Sealed tube; 1 Example 1: Preparation of 2-methyl-4'-(trifluoromethoxy)-[l,l'-biphenyl]-3-carboxylic acid (Metabolite M48) Example 1: Preparation of 2-methyl-4'-(trifluoromethoxy)-[l,l'-biphenyl]-3-carboxylic acid (Metabolite M48) Example 1 was prepared according to a literature procedure (ACS Med. Chem. Lett. 2010, 1, 130-134) using a Suzuki-coupling with Pd(PPh3)4as catalyst and Na2CC>3 as a base in a dioxane/water mixture as solvent in a sealed tube at 130 °C overnight. The reaction mixture was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine and concentrated to give the crude product which was then purified by preparative HPLC.LC/MS (m/z, MH"): 295.21H NMR (400 MHz, DMSO-i/6): δ ppm 2.23 (s, 3 H), 6.94 - 7.01 (m, 1 H), 7.10 (t, J=7.33 Hz, 1 H), 7.33 (dd, J=7.58, 1.52 Hz, 1 H), 7.39 - 7.41 (m, 4 H)
120 g Stage #1: 3-bromo-2-methylbenzoic acid; 4-trifluoromethoxyphenylboronic acid With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 25 - 30℃; for 0.166667h; Stage #2: With potassium carbonate In 1,4-dioxane; water at 80 - 85℃; for 10h; 25 ExampIe-25: Preparation of 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid: (Formula-8) A mixture of 1,4-dioxane (800 ml), 3-bromo-2-methylbenzoic acid (100 gms), 4- (trifluoromethoxy)phenyl)boronic acid (120 gms) and tetrakis(triphenylphosphine)palladium (2 gms) was stirred for 10 minutes at 25-30°C. Aqueous sodium carbonate solution was added to the reaction mixture at 25-30°C. Heated the reaction mixture to 80-85°C and stirred for 10 hours at the same temperature. Cooled the reaction mixture to 25-30°C. Activated carbon (10 gms) was added to the reaction mixture at 25-30°C and stirred for 10 minutes at the same temperature. Filtered the reaction mixture through hy-flow bed and washed the bed with water. To the obtained filtrate, water was added at 25-30°C and washed twice with toluene. Cooled the aqueous layer to 15-20°C. Adjusted the pH of the aqueous layer using aqueous hydrochloric acid solution at 15-20°C. Raised the temperature of reaction mixture to 25-30°C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with water and dried to get the title compound. Yield: 120 gms; M.R: 112-116°C.
  • 5
  • [ 1221722-10-6 ]
  • [ 1799493-16-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 0 - 25 °C 2: triethylamine / dichloromethane / 3 h / 25 °C
  • 6
  • [ 1221722-10-6 ]
  • [ 1799493-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 0 - 25 °C 2: triethylamine / dichloromethane / 3 h / 25 °C
  • 7
  • [ 1221722-10-6 ]
  • [ 1799493-18-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 0 - 25 °C 2: triethylamine / dichloromethane / 3 h / 25 °C 3: sodium hydride / tetrahydrofuran / 14 h / 0 - 80 °C
  • 8
  • [ 1221722-10-6 ]
  • [ 1799493-44-9 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 3h; 2.1 Step 1 : 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carbonyl chloride Step 1 : 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carbonyl chloride To a solution of 2-methyl-4'-(trifluoromethoxy)-[l, -biphenyl]-3-carboxylic acid (3 g, 10.1 mmol) in anhydrous DCM (30 mL), (COCl)2(1.5 g, 12.1 mmol) and DMF (0.1 mL) were added at 0~5°C. After the addition, the reaction mixture was allowed to warm to 25°C and stirred for 3 h. The mixture was concentrated and directly used in step without further purification.
  • 9
  • [ 1221722-10-6 ]
  • [ 2054313-30-1 ]
  • [ 2054313-28-7 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Stage #2: C11H16N2O2 With triethylamine In dichloromethane at 20℃; for 2.5h; 3 Synthesis of erismoester [000580] Synthesis of erismoester: [000581] To a mixture of 10 (80 mg, 0.27 mmol) in 3 mL of DCM in the presence of DMF (1 drop) at 0 °C was added oxalyl chloride (0.04 mL, 0.4 mmol). Then the mixture was stirred at room temperature for 2 hours, and a solution of Ε Ν (0.1 ml, 0.8 mmol) and 6 (40 mg, 0.2 mmol) in 5 mL of DCM was added. The resulting mixture was stirred at room temperature for 2.5 hours, diluted with DCM (20 mL) and washed with water (15 mL). The organic phase was washed with brine (20 mL), dried over anhydrous Na2SC>4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by pre-HPLC (TFA) to give Erismoister as brown oil (80 mg, yield: 82%). LC-MS m/z: 487.1 [M+H]+. LC-MS Purity (214 nm): > 99%; tR = 2.374 min. NMR (400 MHz, CDC13): δ 8.14-8.11 (m, 2H), 7.47-7.28 (m, 7H), 6.71 (d, J = 9.6 Hz, 1H), 4.06-4.02 (m, 2H), 3.79-3.75 (m, 2H), 2.60-2.54 (m, 2H), 2.50 (s, 3H), 1.30-1.28 (m, 6H).
  • 10
  • [ 99548-54-6 ]
  • [ 1221722-10-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene; ethanol / 17 h / 80 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 16 h / 20 °C
Multi-step reaction with 2 steps 1: potassium phosphate monohydrate; palladium diacetate; triphenylphosphine / water; tetrahydrofuran / 20 h / 45 °C / Inert atmosphere; Schlenk technique; Green chemistry 2: sodium hydroxide / 5 h / 75 °C / Green chemistry
  • 11
  • [ 1630035-51-6 ]
  • [ 1221722-10-6 ]
YieldReaction ConditionsOperation in experiment
99% With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 20℃; for 16h; 3 Synthesis of 10: [000578] Synthesis of 10: [000579] A mixture of 9 (260 mg, 0.84 mmol), LiOH.H20 (211 mg, 5 mmol) in 3 mL of THF, 1 mL of methanol and 1 mL of water was stirred at room temperature for 16 hours, and concentrated in vacuo. The residue was diluted with water (2 mL), acidified with 1M HC1 until pH ~3. The suspension was filtered to give 10 as white solid (247 mg, 0.99%). LC-MS m/z: 297.1 [M+H]+. NMR (400 MHz, CDC13): δ 8.06-8.04 (m, 1H), 7.44-7.41 (m, 1H), 7.38-7.28 (m, 5H), 2.51 (s, 3H).
With sodium hydroxide at 75℃; for 5h; Green chemistry;
  • 12
  • [ 926249-35-6 ]
  • [ 1221722-10-6 ]
  • [ 2512200-40-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-(2,6-dimethyl-morpholin-4-yl)pyridin-3-ylamine; 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25 - 30℃; for 0.166667h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25 - 30℃; for 4h; 27 ExampIe-27: Preparation of N-(6-(cis-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyI- 4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide: (Formula-1) A mixture of dimethylformamide (250 ml), 6-(cis-2,6-dimethylmorpholino)pyridin-3- amine (35 gms), 2-methyl-4'-(trifluoromethoxy)-[l,r-biphenyl]-3-carboxylic acid (50 gms), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (40.2 gms) and 1 -hydroxy benzotriazole (2.25 gms) was stirred for 10 minutes at 25-30°C. Diisopropylethylamine (27.1 gms) was added to the reaction mixture at 25-30°C and stirred for 4 hours at the same temperature. Water was slowly added to the reaction mixture at 25-30°C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with water and dried to get the title compound. Yield: 80 gms; Purity by HPLC: 91.79%; Bromo amide impurity: 3.28 %; Desbromo amide impurity: 0.04%; Regio isomer impurity I: 0.1%; Trans isomer impurity: 0.14%; Regio isomer impurity: 0.08%; Unknown impurities: 4.41%.
  • 13
  • [ 926249-35-6 ]
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
120 g Stage #1: 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 45 - 50℃; for 0.666667h; Stage #2: 6-(2,6-dimethyl-morpholin-4-yl)pyridin-3-ylamine In 1-methyl-pyrrolidin-2-one at 45 - 50℃; for 0.75h; 29 Example-29: Preparation of N-(6-(cis-2,6-dimethyImorpholino)pyridin-3-yl)-2-methyl- 4'-(trifluoromethoxy)-[2,1'-biphenyl]-3-carboxamide hydrochloride: (Formula-lc) Thionyl chloride (80.3 gms) was slowly added to the mixture of 2-methyl-4'- (trifluoromethoxy)-[l, -biphenyl]-3-carboxylic acid (100 gms) and N-methylpyrrolidone (500 ml) at 25-30°C. Heated the reaction mixture to 45-50°C and stirred for 40 minutes at the same temperature. 6-(cis-2,6-dimethylmorpholino)pyridin-3 -amine (70 gms) was added to the reaction mixture at 45-50°C and stirred for 45 minutes at the same temperature. Cooled the reaction mixture to 25-30°C. Acetone (1 Its) was added to the reaction mixture at 25-30°C and stirred for 2 hours at the same temperature. Filtered the precipitated solid and washed with acetone. To the obtained compound, methanol (600 ml) was added at 25-30°C and stirred for 10 minutes at the same temperature. Activated carbon was added to the reaction mixture at 25-30°C. Filtered the reaction mixture through hy-flow bed and washed with methanol. Water was slowly added to the obtained filtrate at 25-30°C and stirred for 2 hours at the same temperature. Filtered the solid, washed with water and dried to get the title compound. (0426) Yield: 120 gms; Purity by HPLC: 99.74%.
  • 14
  • [ 1221722-10-6 ]
  • [ 2512200-40-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C
  • 15
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: hydrogen bromide / water; acetone / 4.67 h / 0 - 60 °C
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: hydrogen bromide / water; acetone / 4.67 h / 0 - 60 °C
  • 16
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: acetone / 4.67 h / 0 - 60 °C
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: acetone / 4.67 h / 0 - 60 °C
  • 17
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: acetone / 4.67 h / 0 - 60 °C
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: acetone / 4.67 h / 0 - 60 °C
  • 18
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: acetone / 4.67 h / 0 - 60 °C
  • 19
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: acetone / 4.67 h / 0 - 60 °C
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: acetone / 4.67 h / 0 - 60 °C
  • 20
  • [ 1221722-10-6 ]
  • [ 2512200-41-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: phosphoric acid / methanol / 4.5 h / 0 - 45 °C
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: phosphoric acid / methanol / 4.5 h / 0 - 45 °C
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 2.2: 0.75 h / 25 - 55 °C
Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: hydrogenchloride / acetone / 12 h / 25 - 30 °C 3.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.2: 0.75 h / 25 - 55 °C

  • 21
  • [ 1221722-10-6 ]
  • [ 2512200-41-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: phosphoric acid / acetonitrile / 2.75 h / 0 - 30 °C
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium carbonate / water; dichloromethane / 0.5 h / 25 - 30 °C / Large scale 2.2: 0.75 h / 25 - 60 °C / Large scale
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: phosphoric acid / acetonitrile / 2.75 h / 0 - 30 °C
Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: hydrogenchloride / acetone / 12 h / 25 - 30 °C 3.1: sodium carbonate / water; dichloromethane / 0.5 h / 25 - 30 °C / Large scale 3.2: 0.75 h / 25 - 60 °C / Large scale
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 2.2: 0.75 h / 25 - 55 °C 3.1: methanol / 0.67 h / 25 - 40 °C
Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: phosphoric acid / methanol / 4.5 h / 0 - 45 °C 3.1: methanol / 0.67 h / 25 - 40 °C
Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: hydrogenchloride / acetone / 12 h / 25 - 30 °C 3.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.2: 0.75 h / 25 - 55 °C 4.1: methanol / 0.67 h / 25 - 40 °C
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.67 h / 45 - 50 °C 1.2: 0.75 h / 45 - 50 °C 2.1: sodium hydroxide / water / 0.17 h / 25 - 30 °C 3.1: phosphoric acid / methanol / 4.5 h / 0 - 45 °C 4.1: methanol / 0.67 h / 25 - 40 °C

Reference: [1]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[2]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[3]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[4]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[5]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[6]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[7]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
[8]Current Patent Assignee: ESWARAIAH SAJJA; RAJESHAM BOGE; MSN LABORATORIES PRIVATE LIMITED; PURNA CHNDRASEKHAR REDDY THIPPIREDDY; RAJESHWAR REDDY SAGYAM; VENKATA PANAKALA RAO GOGULAPATI - WO2017/163258, 2017, A1
  • 22
  • [ 1221722-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: hydrogenchloride / acetone / 12 h / 25 - 30 °C
  • 23
  • [ 259269-84-6 ]
  • 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid [ No CAS ]
  • C22H12BrF4NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; methanesulfonyl chloride; In tetrahydrofuran; at 25℃; Its preparation method is:Using <strong>[259269-84-6]3-bromo-5-fluoroanthranilic acid</strong> 2b and 2-methyl-3- (4-trifluoromethoxyphenyl) benzoic acid 3a as starting materials,Preparation of intermediates under the action of methanesulfonyl chloride and pyridine6-chloro-2- [2-methyl-3- (4-trifluoromethoxyphenyl) phenyl] -8-bromo-4H-benzoxazin-4-one 4ab,The reaction temperature is 25 C, and the reaction solvent is tetrahydrofuran;
  • 24
  • 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid [ No CAS ]
  • [ 41198-02-1 ]
  • 8‐bromo‐6‐chloro‐2‐[2‐methyl‐4'‐(trifluoromethoxy)‐[1,1'‐biphenyl]‐3‐yl]‐4H‐3,1‐benzoxazin‐4‐one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanesulfonyl chloride; triethylamine; In acetonitrile; at 25℃; Its preparation method is:Using <strong>[41198-02-1]3-bromo-5-chloroanthranilic acid</strong> 2a and 2-methyl-3- (4-trifluoromethoxyphenyl) benzoic acid 3a as starting materials,Preparation of intermediate 6-chloro-2- [2-methyl-3- (4-trifluoromethoxyphenyl) phenyl] -8-bromo-4H-benzoxazin-4-one 4aa under the action of methanesulfonyl chloride and triethylamine ,The reaction temperature is 25 C, and the reaction solvent is acetonitrile;
  • 25
  • [ 139301-27-2 ]
  • [ 1221722-10-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate monohydrate; palladium diacetate; triphenylphosphine / water; tetrahydrofuran / 20 h / 45 °C / Inert atmosphere; Schlenk technique; Green chemistry 2: sodium hydroxide / 5 h / 75 °C / Green chemistry
  • 26
  • [ 1221722-10-6 ]
  • [ 20776-67-4 ]
  • [ 2573134-78-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanesulfonyl chloride; pyridine / 1,2-dichloro-ethane / 4 - 25 °C 2: 1,2-dichloro-ethane / 25 - 45 °C
  • 27
  • [ 1221722-10-6 ]
  • [ 20776-67-4 ]
  • [ 2573134-93-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine; methanesulfonyl chloride In 1,2-dichloro-ethane at 4 - 25℃; The preparation method is as follows: 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxylic acid 5b and 3-methyl-5-chloroanthranilic acid 6a is the starting material, the intermediate is prepared under the action of methanesulfonyl chloride and pyridine 6-Chloro-2-[2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]]-8-methyl-4H-benzoxazine-4-one 7b, the reaction temperature is 4-25°C, and the reaction solvent is dichloroethane;
  • 28
  • [ 1221722-10-6 ]
  • [ 956697-53-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2: C29H39O3P; caesium carbonate; bis(dibenzylideneacetone)-palladium(0); C48H55ClN2Pd; sodium t-butanolate / 1,4-dioxane; diethylene glycol dimethyl ether / 25 - 100 °C / Sealed tube; Inert atmosphere
  • 29
  • [ 5350-93-6 ]
  • [ 1221722-10-6 ]
  • [ 2585662-28-6 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 12h; 6.2 (2) Synthesis of compound II ompound I (1.0 mmol), 5-amino-2-chloropyridine (1.0 mmol), HAUT (2.0 mmol, 410 mg), triethylamine (4.0 mmol), 4 mL DMF were mixed, and reacted at room temperature for 12 hours. After the reaction is completed, it is diluted with water, extracted with ethyl acetate 3 times, spin-dried under reduced pressure, dried over anhydrous sodium sulfate, and subjected to silica gel column chromatography to obtain a white solid with a yield of 92% (373.3 mg) of II.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1221722-10-6 ]

Fluorinated Building Blocks

Chemical Structure| 330-12-1

[ 330-12-1 ]

4-(Trifluoromethoxy)benzoic acid

Similarity: 0.93

Chemical Structure| 1014-81-9

[ 1014-81-9 ]

3-(Trifluoromethoxy)benzoic acid

Similarity: 0.91

Chemical Structure| 148438-00-0

[ 148438-00-0 ]

Methyl 3-(trifluoromethoxy)benzoate

Similarity: 0.90

Chemical Structure| 4315-07-5

[ 4315-07-5 ]

4-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.89

Chemical Structure| 4837-20-1

[ 4837-20-1 ]

4-(Difluoromethoxy)benzoic acid

Similarity: 0.89

Aryls

Chemical Structure| 330-12-1

[ 330-12-1 ]

4-(Trifluoromethoxy)benzoic acid

Similarity: 0.93

Chemical Structure| 1014-81-9

[ 1014-81-9 ]

3-(Trifluoromethoxy)benzoic acid

Similarity: 0.91

Chemical Structure| 148438-00-0

[ 148438-00-0 ]

Methyl 3-(trifluoromethoxy)benzoate

Similarity: 0.90

Chemical Structure| 4315-07-5

[ 4315-07-5 ]

4-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.89

Chemical Structure| 4837-20-1

[ 4837-20-1 ]

4-(Difluoromethoxy)benzoic acid

Similarity: 0.89

Ethers

Chemical Structure| 330-12-1

[ 330-12-1 ]

4-(Trifluoromethoxy)benzoic acid

Similarity: 0.93

Chemical Structure| 1014-81-9

[ 1014-81-9 ]

3-(Trifluoromethoxy)benzoic acid

Similarity: 0.91

Chemical Structure| 148438-00-0

[ 148438-00-0 ]

Methyl 3-(trifluoromethoxy)benzoate

Similarity: 0.90

Chemical Structure| 4315-07-5

[ 4315-07-5 ]

4-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.89

Chemical Structure| 4837-20-1

[ 4837-20-1 ]

4-(Difluoromethoxy)benzoic acid

Similarity: 0.89

Carboxylic Acids

Chemical Structure| 330-12-1

[ 330-12-1 ]

4-(Trifluoromethoxy)benzoic acid

Similarity: 0.93

Chemical Structure| 1014-81-9

[ 1014-81-9 ]

3-(Trifluoromethoxy)benzoic acid

Similarity: 0.91

Chemical Structure| 4315-07-5

[ 4315-07-5 ]

4-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.89

Chemical Structure| 4837-20-1

[ 4837-20-1 ]

4-(Difluoromethoxy)benzoic acid

Similarity: 0.89

Chemical Structure| 203302-97-0

[ 203302-97-0 ]

3-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.88

Trifluoromethyls

Chemical Structure| 330-12-1

[ 330-12-1 ]

4-(Trifluoromethoxy)benzoic acid

Similarity: 0.93

Chemical Structure| 1014-81-9

[ 1014-81-9 ]

3-(Trifluoromethoxy)benzoic acid

Similarity: 0.91

Chemical Structure| 148438-00-0

[ 148438-00-0 ]

Methyl 3-(trifluoromethoxy)benzoate

Similarity: 0.90

Chemical Structure| 4315-07-5

[ 4315-07-5 ]

4-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.89

Chemical Structure| 203302-97-0

[ 203302-97-0 ]

3-(Trifluoromethoxy)phenylacetic acid

Similarity: 0.88