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Chemical Structure| 171243-30-4 Chemical Structure| 171243-30-4

Structure of 171243-30-4

Chemical Structure| 171243-30-4

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CAS No.: 171243-30-4

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Product Details of [ 171243-30-4 ]

CAS No. :171243-30-4
Formula : C8H3ClF4O
M.W : 226.56
SMILES Code : O=C(Cl)C1=CC(C(F)(F)F)=CC(F)=C1
MDL No. :MFCD00061157
InChI Key :BGAKSLBTFLVNAH-UHFFFAOYSA-N
Pubchem ID :519364

Safety of [ 171243-30-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:Ⅱ

Application In Synthesis of [ 171243-30-4 ]

* 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 [ 171243-30-4 ]

[ 171243-30-4 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 159706-35-1 ]
  • [ 171243-30-4 ]
  • [ 171243-04-2 ]
  • 2
  • [ 171243-30-4 ]
  • [ 501701-42-4 ]
  • <i>N</i>-[1-(2,4-dimethoxy-benzyloxycarbamoyl)-2-hydroxy-ethyl]-3-fluoro-5-trifluoromethyl-benzamide [ No CAS ]
  • 3
  • [ 4149-06-8 ]
  • [ 171243-30-4 ]
  • 3-fluoro-<i>N</i>-(5-oxo-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-3-yl)-5-trifluoromethyl-benzamide [ No CAS ]
  • 4
  • [ 6638-79-5 ]
  • [ 171243-30-4 ]
  • [ 329941-91-5 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine; In chloroform; at 0 - 20℃; for 3.75h; ) Compound 1.2 Acyl chloride 1.1 (5.00 g, 21.0 mmol) was added dropwise to an ice-cold solution of MeNH(OMe).HCl (2.80 g, 28.1 mmol) and Et3N (9.00 mL, 63.9 mmol) in CHCl3 (50 mL). The reaction mixture was stirred at 0C for 45 min and at room temperature for 3 h then was concentrated under reduced pressure. The residue was partitioned between water and EtOAc. The organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give compound 1.2 (4.78 g, 91% yield) as a brown oil.
With triethylamine; In chloroform; at 0 - 20℃; for 1h; Into a round-bottom flask equipped with a stir bar and nitrogen on demand were placed N,O-dimethylhydroxylamine hydrochloride (2.80 g, 28.7 mmol), Et3N (9.0 mL, 64.57 mmol) and CHCl3 (50 mL). The solution was cooled to 0C and 3-trifluoromethyl-5-fluorobenzoyl chloride (5.0 g, 22.07 mmol) was added dropwise over several minutes. The resulting solution was allowed to stir at 0C for 30 min, after which time it was allowed to warm to rt and stir for an additional 30 min. The mixture was then poured into a separatory funnel containing ethyl acetate and water. The organic layer was collected and was washed with water, brine, dried over MgSO4, filtered and the solvents were removed under reduced pressure to provide 68 as a clear oil which was used without any further purification. 1H NMR (CDCl3, 300 MHz) δ 7.83 (s, 1H), 7.65 (d, J= 9 Hz, 1H), 7.46 (d, J= 9 Hz, 1H), 3.59 (s, 3H), 3.42 (s, 3H).
  • 5
  • [ 4294-57-9 ]
  • [ 171243-30-4 ]
  • (3-fluoro-5-trifluoromethyl-phenyl)-<i>p</i>-tolyl-methanone [ No CAS ]
  • 11
  • [ 171243-30-4 ]
  • GW4511 [ No CAS ]
  • 12
  • [ 171243-30-4 ]
  • 2-[4-chloro-2-(3-fluoro-5-trifluoromethyl-benzoyl)-phenoxy]-<i>N</i>-[2-methyl-4-(3-sulfamoyl-propoxy)-phenyl]-acetamide [ No CAS ]
  • 13
  • [ 171243-30-4 ]
  • [ 170729-83-6 ]
  • 14
  • [ 171243-30-4 ]
  • [ 171243-05-3 ]
  • 15
  • [ 171243-30-4 ]
  • 5-{(2R,3S)-2-[(R)-1-(3-Fluoro-5-trifluoromethyl-phenyl)-ethoxy]-3-phenyl-morpholin-4-ylmethyl}-2,4-dihydro-[1,2,4]triazol-3-one [ No CAS ]
  • 16
  • [ 171243-30-4 ]
  • (2-{(2R,3S)-2-[(R)-1-(3-Fluoro-5-trifluoromethyl-phenyl)-ethoxy]-3-phenyl-morpholin-4-yl}-1-hydrazono-ethyl)-carbamic acid methyl ester [ No CAS ]
  • 17
  • 5-amino-2-chloro-N-(5-fluoropyridin-3-yl)benzamide [ No CAS ]
  • [ 171243-30-4 ]
  • 2-chloro-N-(5-fluoropyridin-3-yl)-5-[3-fluoro-5-(trifluoromethyl)benzoyl]amino}-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25℃; for 12h; 2-Chloro-N-r5-fluorot3yridin-3-yl)-5-{r3-flυoro-5-rtrifluoromethyl)benzoyl1aminol- benzamide A solution of 5-amino-2-chloro-N-(5-fluoropyridin-3-yl)benzamide (Method 79; 124 mg, 0.466 mmol) and DlEA (405 μL, 2.33 mmol, 5.0 equiv) in THF (2.0 ml) was treated with 3-fluoro-5-(trifluorottiethyl)benzoyl chloride (131 mg, 0.582 mmol, 1.25 equiv). The reaction mixture was stirred for 12 h at 25 C. The reaction was quenched with 10% NaOH and extracted with EtOAc. The organics were dried with ΝaCl(sat) and then Na2SO4^) and removed under reduced pressure. The residue was purified directly by Gilson reverse phase preparatory Hl3LC (5-95% MeCN/H2O) to give 75 mg of product (35%). NMR: 11.11 (s, IH), 10.80 (s, IH), 8.68 (s, I H), 8.37 (s, IH), 8.18-8.12 (m, 3H), 8.03-7.93 (M, 3H), 7.63 (d, IH); m/z 456.
  • 18
  • [ 1772-01-6 ]
  • [ 171243-30-4 ]
  • 3-(pyridin-2-yl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3-(2-Pyridyl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole 3-Fluoro-5-trifluoromethylbenzoyl chloride (0.11 mL, 0.73 mmol) was added in a dropwise manner to a solution of pyridylamidoxime (99.3 mg, 0.73 mmol) in dichloromethane (10 mL) under argon. The reaction mixture was stirred at room temperature for 10 minutes and the solvent was removed in vacuo. DMF (4 ml) was added to the oily residue and the resulting solution was stirred at 120 C. for 16 h under argon. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo. Flash chromatography on silica gel (15%-20% ethyl acetate in hexanes) yielded 150 mg (66.9%, GC/MS product RT 7.59 min, 98% purity) of 3-(2-pyridyl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.86 (d, 1H), 8.40 (s, 1H), 8.24 (d, 1H), 8.18 (d, 1H), 7.90 (dt, 1H), 7.59 (d, 1H), 7.49 (m, 1H).
  • 19
  • MSproduct RT [ No CAS ]
  • [ 327056-58-6 ]
  • [ 171243-30-4 ]
  • 3-(5-fluoro-pyridin-2-yl)-5-(3-fluoro-5-trifluoromethylphenyl)-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-trifluoromethylphenyl)-1,2,4-oxadiazole 3-Fluoro-5-trifluoromethylbenzoyl chloride (0.10 mL, 0.65 mmol) was added to a solution of 5-fluoropyridylamidoxime (102.9 mg, 0.66 mmol) in dichloromethane (2 mL). The solution was stirred at room temperature for 10 minutes and then concentrated in vacuo. DMF (4 mL) was added to the residue and the resulting solution was stirred at 120 C. for 16 h under argon. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo. Flash chromatography on silica gel (10%-20% ethyl acetate in hexane) yielded 131.1 mg (62.5%, GC/MSproduct RT 7.34 min, 96% pure) of 3-(5-fluoro-2-pyridyl) -5-(3-fluoro-5-trifluoromethylphenyl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.70 (d, 1H), 8.38 (s, 1H), 8.28 (dd, 1H), 8.17 (d, 1H), 7.60 (dt, 2H).
  • 20
  • piperidinomethylpolystyrene [ No CAS ]
  • [ 226249-95-2 ]
  • [ 171243-30-4 ]
  • [ 226238-54-6 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In methanol; dichloromethane; chloroform; EXAMPLE 240 Preparation of (R)-3-[N-(3-Fluoro-5-{trifluoromethyl)benzoyl}glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compound No. 1191) A solution of 3-fluoro-5-(trifluoromethyl)benzoyl chloride (0.058 mmol) in dichloromethane (1 mL) was added to a mixture of (R)-1-(3,5-dimethylisoxazol-4-ylmethyl)-3-(glycylamino)pyrrolidine (0.050 mmol) and piperidinomethylpolystyrene (58 mg) in chloroform (0.2 mL) and dichloromethane (0.75 mL). After the reaction mixture was stirred at room temperature for 2 h, methanol (1.0 mL) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was loaded onto Varian SCX column, and washed with CH3OH (16 mL). Product was eluted off using 2 N NH3 in CH3OH (6 mL) and concentrated to afford (R)-3-[N-(3-fluoro-5-(trifluoromethyl)benzoyl}glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compound No. 1191) (19.5 mg, 88%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 443.2 (M++H, C20H22F4N4O3).
  • 21
  • piperidinomethylpolystyrene [ No CAS ]
  • [ 226249-95-2 ]
  • NH3in methanol [ No CAS ]
  • [ 171243-30-4 ]
  • [ 226238-54-6 ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; chloroform; [Example 240] Synthesis of (R)-3- [N-(3-fluoro-5-(trifluoromethyl)benzoyl]glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compd. No. 1191) A dichloromethane solution (1 mL) of 3-fluoro-5-(trifluoromethyl)benzoyl chloride (0.058 mmol) was added to a solution of (R)-1-(3,5-dimethylisoxazol-4-ylmethyl)-3-(glycylamino)pyrrolidine (0.050 mmol) and a piperidinomethylpolystyrene (58 mg) in chloroform (0.2 mL) and dichloromethane (0.75 ml). The reaction mixture was stirred at room temperature for 2 hours, and methanol (1.0 mL) was then added. The resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was loaded onto a Varian SCX column and washed with methanol (16 mL). The obtained crude product was eluted with a solution of 2 M NH3in methanol (6 mL) and concentrated to provide (R)-3-[N-[3-fluoro-5-(trifluoromethyl)benzoyl]glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compd. No. 1191) (19.5 mg, 88%). The purity wasdetermined by RPLC/MS (100%). ESI/MS m/e 443.2 (M++H, C20H22F4N4O3).
  • 22
  • [ 42122-75-8 ]
  • [ 171243-30-4 ]
  • [ 942631-59-6 ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine; In dichloromethane; at 0℃; for 1.5h; Method 19; Methyl 2-chloro-5-{r3-fluoro-5-(trifluoromethyl)benzoyl1amino}benzoate; To a solution of methyl 5-amino-2-chlorobenzoate (Method 24, 2.25 g, 12.1 mmol) and triethylamine (2.53 ml, 18.2 mmol) in DCM (15 ml) at O0C was added 3-fluoro-5-(trifluoromethyl)benzoyl chloride (3.02 g, 13.3 mmol). After 1.5 hours, the reaction mixture was diluted with DCM (100 ml), washed with IN HCl (30 ml), water (30 ml), brine (30 ml) and dried (MgSO4). The crude product was recrystallized from EtOAc:Hex (3 crops) to give 3.55 g (78%) white solid. <n="53"/>1H NMR CDCl3 8.05 (s, 1 H), 7.86 (m, 3 H), 7.79 (d, 1 H), 7.55 (d, 1 H), 7.48 (d, 1 H), 3.94 (S5 3 H); m/z: 374.
  • 23
  • [ 35944-64-0 ]
  • [ 171243-30-4 ]
  • [ 1036376-89-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 25℃; for 16.75h; Example 19 : 3-Fluoro-N- [4-methyl-3-(9H-pyrimido [4,5-b] indol-7-yl)phenyl] -5-(trifluoro- methyl)benzamideStep 1: 3-Fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide3-Iodo-4-methylaniline (2.42 g, 10.4 mmol) was dissolved in DCM (20.00 mL) and triethylamine (TEA) (1.70 mL, 12.2 mmol) was added and the resulting mixture was cooled to 0 0C. To the mixture was added dropwise 3-fluoro-5-(trifluoromethyl)benzoyl chloride (1.60 mL, 10.5 mmol) and the resulting mixture was stirred at 0 0C for 45 minutes and at 25 0C for 16 hours. The reaction was extracted with ethyl acetate and the organic extracts were washed with water sat. Na2CCh, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The reaction product was used in the next reaction without purification. 1H NMR(CDCl3): δ 8.98 (d, IH), 7.78 (s, IH), 7.72 (m, 2H), 7.55 (m, 2H), 7.23 (d, IH), 2.42 (s, 3H). MS (EI) m/z = 424 (M+H).
  • 24
  • [ 925897-75-2 ]
  • [ 171243-30-4 ]
  • 5-(((3-fluoro-5-(trifluoromethyl)phenyl)carbonyl)amino)-2-methyl-N-(2-((4-(4-methyl-1-piperazinyl)phenyl)amino)-5-pyrimidinyl)benzamide [ No CAS ]
  • 25
  • C17H26FN5O2*ClH [ No CAS ]
  • [ 171243-30-4 ]
  • [ 1134775-91-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; To tert-Znrtyl 2-((R)-l-(5-((2R,5S)-2,5-dimethylpyrrolidine-l-carbonyl)-3-fluoropyridin-2- yl)ethylcarbamoyl)-2-ethylhydrazinecarboxylate (25 mg, 0.06 mmol) is added a solution of HCl in MeOH (3N, 1 mL). The reaction mixture is stirred at RT for 2 h and then concentrated <n="110"/>to dryness. No purification step is required, a he isolated hydrochloride is utilized in the next reaction.The hydrochloride (20 mg, 0.05 mmol) is dissolved in DMF (0.5 mL), treated withDIPEA (90 μL, 0.52 mmol) and 3-fluoro-5-(trifluoromethyl)benzoyl chloride (10 mg, 0.08 mmol) and stirred 2 h at RT. Then the mixture was concentrated in vacuo and the residue was purified by reversed phase HPLC using a gradient of ACN in water with 0.1% TFA to give the title compound. MS (m/z): 541.8 [M+H+]
  • 26
  • C13H18ClN3O3*ClH [ No CAS ]
  • [ 171243-30-4 ]
  • [ 1134777-19-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; To (R)-t?r/-butyl 2-(l -(2-chloro-4-(methoxycarbonyl)phenyl)ethylcarbamoyl)-2- ethylhydrazinecarboxylate (75 mg, 0.19 mmol) is added a solution of HCl in MeOH (3 N, 2 mL). The reaction mixture is stirred at RT for 14 h and then concentrated to dryness. No purification step is required, and the isolated title compound is utilized in the next reaction.The hydrochloride (63 mg, 0.19 mmol) is dissolved in DMF (1.0 mL), treated with DIPEA (163 μL, 0.94 mmol) and 3-fluoro-5-(trifluoromethyl)benzoyl chloride (47 mg, 0.21 mmol) and stirred 2 h at RT. Then the mixture was concentrated in vacuo and the residue was purified by chromatography on silica gel (n-hexan/EA). MS (m/z): 489.6 [M+H*]
  • 27
  • [ 5855-97-0 ]
  • [ 171243-30-4 ]
  • [ 1363454-10-7 ]
  • 28
  • [ 623-12-1 ]
  • [ 171243-30-4 ]
  • [ 329941-92-6 ]
  • 29
  • 2-methoxy-5-chlorophenylmagnesium bromide [ No CAS ]
  • [ 171243-30-4 ]
  • [ 1364739-51-4 ]
  • [ 329941-92-6 ]
  • 30
  • [ 171243-30-4 ]
  • 4-{2-[4-chloro-2-(3-fluoro-5-trifluoromethylbenzoyl)phenoxy]acetylamino}-2-fluoro-3-methylbenzoic acid [ No CAS ]
  • 31
  • [ 171243-30-4 ]
  • 4-{2-[4-chloro-2-(3-fluoro-5-trifluoromethylbenzoyl)phenoxy]acetylamino}-2-fluoro-3-methylbenzoic acid [ No CAS ]
  • [ 1364740-54-4 ]
  • [ 1364740-36-2 ]
  • 32
  • C18H19N2O2Pol [ No CAS ]
  • [ 171243-30-4 ]
  • C26H21F4N2O3Pol [ No CAS ]
 

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