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Chemical Structure| 175204-88-3 Chemical Structure| 175204-88-3

Structure of 175204-88-3

Chemical Structure| 175204-88-3

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Product Details of [ 175204-88-3 ]

CAS No. :175204-88-3
Formula : C13H10F3NO2S
M.W : 301.28
SMILES Code : CCOC(=O)C1=CSC(=N1)C1=CC=C(C=C1)C(F)(F)F
MDL No. :MFCD00179674
InChI Key :SCZAGGBIOXLKPW-UHFFFAOYSA-N
Pubchem ID :2737237

Safety of [ 175204-88-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318
Precautionary Statements:P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501
Class:8
UN#:1759
Packing Group:

Application In Synthesis of [ 175204-88-3 ]

* 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 [ 175204-88-3 ]

[ 175204-88-3 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 70-23-5 ]
  • [ 72505-21-6 ]
  • [ 175204-88-3 ]
YieldReaction ConditionsOperation in experiment
63% In acetone; for 3h;Heating / reflux; To a stirred solution of 4-trifluoromethylthiobenzamide (205 g, 10 mmol) in acetone (10 mL) was added ethyl bromopyruvate (1.95 g, 10 mmol) in acetone (10 mL) dropwise. The mixture was stirred under reflux for 3 h. After cooling to room temperature, the solution was concentrated and purified by column chromatography to give 1.9 g (63%) of cpd Q1 as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.23 (s, 1H), 8.14 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 4.46 (q, J=7.1 Hz, 2H) 1.44(t, J=7.1 Hz, 3H); MS (ES) m/z: 302 (M+H+).
  • 2
  • [ 175204-88-3 ]
  • [ 19578-68-8 ]
  • [ 870280-38-9 ]
YieldReaction ConditionsOperation in experiment
18% With copper(l) iodide; triethylamine;palladium diacetate; triphenylphosphine; In DMF (N,N-dimethyl-formamide); at 130℃; for 12h; Compound 7; (R)-2-[5-(4-Benzyloxyphenyl)-2-(4-trifluoromethylphenyl)thiazole-4-carbonyl]amino}- 3-benzylsulfanylpropionic acid; Step A: 5-( 4-Benzyloxyphenyl)-2-( 4-trifluoromethylphenyl)thiazole-4-carboxylic acid ethyl ester; A mixture of 2- (4-trifluoromethylphenyl)thiazole-4-carboxylic ethyl ester (commercially available, 301 mg, 1.0 mmol), 4-benzyloxy-1-iodobenzene (620 mg, 2.0 mmol), palladium acetate (22 mg, 0.1 mmol), copper (I) iodide (381 mg, 2.0 mmol), triphenylphosphine (52 mg, 0.2 mmol) and triethylamine (0.28 mL, 2.0 mmol) in dimethyl formamide (3.0 mL) was heated at 130C for 12 h. It was then cooled to room temperature and diluted with ethyl acetate (15 mL). After washing with water multiple times, the organic layer was separated, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the crude product. Purification of the crude product by medium pressure liquid chromatography on silica gel (1: 9 ethyl acetate/hexanes) gave 85 mg (18%) of the title compound. MS 484.1 (M+H)+.
  • 3
  • [ 1221437-20-2 ]
  • [ 175204-88-3 ]
  • 4
  • [ 1332708-70-9 ]
  • [ 175204-88-3 ]
YieldReaction ConditionsOperation in experiment
86% With oxygen; copper diacetate; In N,N-dimethyl-formamide; at 120℃; under 760.051 Torr; for 12h;Molecular sieve; General procedure: To a solution of 4-carboxythiazoline or 4-carboxyoxazoline (0.5 mmol) in anhydrous DMF (1 mL) were added molecular sieves (4 Å, 100% wt) and Cu(OAc)2 (9.1 mg, 0.05 mmol). The reaction mixture was stirred with an O2 balloon at 120 C for 10-24 h. The resulting mixture was diluted with ethyl acetate and the solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford 4-carboxythiazole or 4-carboxyoxazole.
  • 5
  • [ 175204-88-3 ]
  • [ 1373148-71-0 ]
  • [ 1373143-63-5 ]
YieldReaction ConditionsOperation in experiment
321 mg 1N Aqueous solution of sodium hydroxide (2 ml) was added at room temperature to a solution of 2-[4-(trifluoromethyl)phenyl]thiazole-4-carboxylic acid ethyl ester (300 mg) described in Reference Example 178 in tetrahydrofuran (2 ml) and stirred at 50 C. for 4.5 hours. After the reaction, 1N aqueous solution of hydrochloric acid (2 ml) was added, the solvent was evaporated and the residue was azeotropically distilled twice with toluene. N,N-Dimethylformamide (catalytic amounts) and thionyl chloride (2 ml) were added to the resulting residue at room temperature, stirred at 80 C. for an hour, and an excess amount of thinly chloride was evaporated. The resulting reaction solution was dissolved in dichloromethane (5 ml), triethylamine (416 μl) and 5-methyl-6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridine-3-amine (327 mg) were added and stirred at room temperature for 20 minutes. After the reaction, water was added, extracted with chloroform and the solvent was evaporated. The resulting residue was purified with a basic silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (321 mg) as a white solid. [1109] MS (ESI) m/z: 529 (M+H)+.
  • 6
  • (4-Trifluoromethyl-benzoylamino)-acetic acid ethyl ester [ No CAS ]
  • [ 175204-88-3 ]
  • 7
  • C13H12F3NO4 [ No CAS ]
  • [ 175204-88-3 ]
YieldReaction ConditionsOperation in experiment
With Lawessons reagent; In 1,4-dioxane; for 12h;Reflux; General procedure: The mixture of the 7b (1.96g, 8.35 mmole) and Lawesson’s reagent (6.73 g, 16.68 mmole) in dry 1, 4 Dioxane(25 mL) was heated to reflux overnight. The reaction mixture was then evaporated under reduced pressure and purified by passing through silica gelwith petroleum ether/ethyl acetate to afford pure solid product 4b (81%).
  • 8
  • [ 175204-88-3 ]
  • [ 288161-17-1 ]
  • 9
  • [ 175204-88-3 ]
  • 5-{2-[4-(trifluoromethyl)phenyl]thiazol-4-yl}-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
  • 11
  • [ 455-19-6 ]
  • [ 868-59-7 ]
  • [ 175204-88-3 ]
  • 12
  • [ 175204-88-3 ]
  • (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-2-(4-(trifluoromethyl)phenyl)thiazole-4-carboxamide [ No CAS ]
  • 13
  • [ 175204-88-3 ]
  • [ 144061-16-5 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; at 80℃; for 12h; General procedure: Toan oven-dried round bottom flask charged withethyl 2-(4-chlorophenyl)thiazole-4-carboxylate,55(176 mg, 0.62 mmol,1.0 equiv.) THF (6 mL) and MeOH (2mL) was added LiOH.H2O (78 mg, 1.86 mmol,3.0 equiv.).The reaction mixture was allowed to stir at 80 for 12 hr.The reaction mixture was cooled toroom temperatureand neutralized with 1N HCl. The resulting solution was extracted with ethyl acetate.The combined organic layer was dried overMgSO4,filtered,and concentrated under reduced pressureto give 2-(4-chlorophenyl) thiazole-4-carboxylic acid.
  • 14
  • [ 41731-52-6 ]
  • [ 128796-39-4 ]
  • [ 175204-88-3 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 90℃; for 12h; General procedure: Toan oven-dried round bottom flask charged withethyl 2-chlorothiazole-4-carboxylate(500 mg, 2.60 mmol, 1.0 equiv.), toluene (10 mL),Pd(PPh3)4(150 mg, 0.13 mmol, 0.05 equiv.), DPPF (43 mg, 0.08 mmol, 0.03 equiv.), and saturated aqueous K2CO3solution (720 mg, 5.20 mmol, 2.0 equiv. in 1mL H2O) was added 4-chlorophenylboronic acid(813 mg, 5.20 mmol, 2.0 equiv.).The reaction mixture was allowed to stir at 90oC for 12 h. The reaction mixture wascooled to room temperature, 2N NaOH solution and the resulting mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified byMPLC (24g-silica-gel,n-hexanes/EtOAc)to affordethyl 2-(4-chlorophenyl)thiazole-4-carboxylate.
  • 15
  • [ 100367-77-9 ]
  • [ 128796-39-4 ]
  • [ 175204-88-3 ]
YieldReaction ConditionsOperation in experiment
16% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,2-dimethoxyethane; for 43h;Schlenk technique; Inert atmosphere; General procedure: A predried 20 ml Schlenk tube with magnetic stirring bar was charged with 5 mol-% PdC Cdppf), 1.0 eq aryl halide, 1 .0-1.3 eq boronic acid and 2.1 eq cesium fluoride in anhydrous DME. The reaction mixture was degassed by evacuation and purging with Ar (repeated three times) and placed in an oil bath at 80 C. After stirring for 21 -96 h (reaction control via TLC and GC/MS) the reaction mixture was cooled to RT and filtered through a pad of Celite. The filter cake was washed with an appropriate amount of EtOAc, the volatiles were removed under reduced pressure and the crude residue was died in oil-pump vacuum. Pure product was obtained via flash column chromatography (S1O2, cycl o h exa ne/EtO Ac or toluene/EtOAc), unless otherwise stated.
  • 16
  • [ 175204-88-3 ]
  • [ 857284-25-4 ]
  • 17
  • [ 175204-88-3 ]
  • (2-oxo-2-((2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)methoxy)ethyl)triphenylphosphonium bromide [ No CAS ]
  • 18
  • [ 175204-88-3 ]
  • C13H9BrF3NO2S [ No CAS ]
 

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