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[ CAS No. 654-70-6 ] {[proInfo.proName]}

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Chemical Structure| 654-70-6
Chemical Structure| 654-70-6
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Product Details of [ 654-70-6 ]

CAS No. :654-70-6 MDL No. :MFCD00042155
Formula : C8H5F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PMDYLCUKSLBUHO-UHFFFAOYSA-N
M.W : 186.13 Pubchem ID :522170
Synonyms :

Calculated chemistry of [ 654-70-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.56
TPSA : 49.81 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 3.32
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 2.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.694 mg/ml ; 0.00373 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.58 mg/ml ; 0.00311 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.181 mg/ml ; 0.000973 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 654-70-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P272-P280-P301+P312+P330-P302+P352-P333+P313-P362+P364-P501 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 654-70-6 ]

* 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 [ 654-70-6 ]

[ 654-70-6 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 79-41-4 ]
  • [ 654-70-6 ]
  • [ 90357-53-2 ]
YieldReaction ConditionsOperation in experiment
92.1% <Reference Example 1>; A reaction container was charged with 70 g of commercially available 4-cyano-3-trifluoromethylaniline (LC surface percentage: 99.39%) and 350 mL of ethanol, and the temperature was increased to 72C. After the mixture was stirred at 72 to 75C for 30 minutes, insoluble matters were removed by filtration at the same temperature and the mixture was further washed with 10 mL of ethanol. The filtrate thus obtained was cooled to 57C, and 360 mL of water was dropped at the same temperature over about 4 hours. 30 mg of 4-cyano-3-trifluoromethylaniline that had been previously purified was seeded thereto and the resultant mixture was cooled to 45C, and thereafter stirred at the same temperature for 30 minutes. Then, the mixture was cooled to 25C and stirred at the same temperature for 1 hour. Crystals were separated by filtration and washed with a mixed solvent of 56 mL of ethanol and 56 mL of water to give 83.81 g of wet crystals. The wet crystals were dried under reduced pressure to obtain 50.61 g of 4-cyano-3-trifluoromethylaniline. The LC surface percentage was 99.90%, and the yield was 72.3%. A reaction container was charged with 68 mL of N,N-dimethylacetamide, 22.1 g of methacrylic acid, and 38 mg of dibutylhydroxytoluene, and the temperature was reduced to -5C. Thionyl chloride in an amount of 30.6 g was dropped thereto at -3.8 to 0.3C over 50 minutes, and the mixture was kept at -4.0 to -0.8C for 30 minutes. A solution obtained by dissolving 36.0 g of 4-cyano-3-trifluoromethylaniline obtained as described above in 79 mL of N,N-dimethylacetamide was dropped into the reaction container at -5.3 to 0C over 65 minutes. The container for dropping was washed with 11 mL of N,N-dimethylacetamide, the washing liquid was added to the reaction solution, and the solution was kept at -5.3 to 0C for 1 hour. After completion of the reaction, the obtained reaction solution was dropped to a mixed solution of 306 mL of ethyl acetate and 252 mL of water at 20C or less. The solution was washed with 18 mL of N,N-dimethylacetamide and the washing solution and the mixed solution were combined, and 378.1 g of an aqueous 16% sodium carbonate solution was added to the solution to adjust the pH to 7.1. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 1.7 m/hr. The organic layer was added with 571.8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 9 m/hr. The organic layer was added with 571.8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 6 m/hr. The organic layer was further added with 571. 8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and then made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 0 m/hr. Then, the organic layer was charged with 180 mL of chlorobenzene, and ethyl acetate and chlorobenzene were distilled out in an amount of 222.3 g by vacuum concentration. Next, 504 mL of chlorobenzene, 1.8 g of activated carbon and 4.9 g of gamma-alumina were charged and the mixture was stirred at 75C for 30 minutes. The alumina and activated carbon were separated by filtration at the same temperature and washed with 36 mL of chlorobenzene. The filtrate and the washing solution were combined, and 545.5 g of chlorobenzene was distilled out by vacuum concentration, and then the mixture was cooled to 20C and stirred at 15 to 20C for 2 hours. Crystal were separated by filtration and washed with 108 mL of a chlorobenzene solution dissolved with 0.45 g of dibutylhydroxytoluene to give 48.94 g of wet crystals. After drying the crystal under reduced pressure, 45.27 g of crystals of N-methacryloyl-4-cyano-3-trifluoromethylaniline was obtained. The LC surface percentage was 99.92%, and the yield was 92.1%.
  • 2
  • [ 3586-58-1 ]
  • [ 654-70-6 ]
  • [ 888071-25-8 ]
  • 3
  • 1-(4-fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carbonyl chloride [ No CAS ]
  • [ 654-70-6 ]
  • 1-(4-fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 4
  • 1-(4-fluoro-benzyl)-4-methyl-2-oxo-imidazolidine-4-carbonyl chloride [ No CAS ]
  • [ 654-70-6 ]
  • 1-(4-fluoro-benzyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 5
  • [ 654-70-6 ]
  • [ 261904-39-6 ]
  • [ 206193-17-1 ]
YieldReaction ConditionsOperation in experiment
84% To a solution of (R)-XIX-I in DMA (dimethylacetamide) (0.55M) cooled at -100C, 1.3 eq. of SOCl2 were added drop wise under nytrogen atmosphere. The solution was stirred at this temperature for 3 h, and a solution of 4-amino-2- (trifluoromethyl)benzonitrile (XVII-I, Scheme 1) in DMA (1.2 eq. of amine in 1.5 mL of DMA) was added drop wise. The reaction mixture was than allowed to react at room temperature for 16 h. The solvent was than removed under reduced pressure, and the crude material was treated with saturated NaHCO3 and extracted with EtOAc. The reaction crude was purified by silica gel column chromatography. Yield:
80.4% With thionyl chloride; In N,N-dimethyl acetamide; at -15 - 40℃; for 3.5h; Compound R-III (6.00 g, 32.9 mmol),4-cyano-3-trifluoromethylaniline (6.79 g, 36.5 mmol)Add N,N-methylacetamide (42 mL) to the reaction flask and cool to -15 C in an ice bath.Thionyl chloride (4.60 g, 39.0 mmol) was added dropwise, and the reaction temperature was controlled from -10 C to -15 C.After the dropwise addition was completed, the mixture was stirred for 0.5 h, and then raised to 40 C for 3 h.The reaction was slowly poured into cold saturated sodium bicarbonate solution (120 mL).Extract with ethyl acetate (30 mL x 3), combine the organic phases and wash with saturated sodium chloride.Filtration and evaporation of the solvent under reduced pressure afforded crude material.Recrystallization from a mixed solution of petroleum ether and methyl tert-butyl ether, decolorization of activated carbon,Obtained white solid R-IV 9.30g, yield 80.4%,
77.0% To a cold solution of bromoacid1 3 (0.29 mol) in 300 mL of THF was added SOCl2 (0.39 mol) in a dropwise manner under an argon atmosphere. The reaction mixture was stirred for 3 h under an ice-water bath and then Et3N (0.39 mol), aniline (1, 2, 0.19 mol) were added. The reaction mixture was stirred for 20 h at room temperature and concentrated under reduced pressure to give a solid which was treated with 300 mL of H2O. The solution was extracted with EtOAc (2×400 mL) and combined EtOAc extracts were washed with saturated NaHCO3 solution (2×300 mL) and brine (300 mL), successively. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give an oil which was purified by column chromatography using CH2Cl2/EtOAc (8:2) to give a solid which was recrystallized from EtOAc/hexane to give a target compound. 1) Kirkovsky, L.; Mukheijee, A.; Yin, D.; Dalton, J. T.; Miller, D. D. Chiral nonsteroidal affinity ligands for the androgen receptor. 1. Bicalutamide analogues bearing electrophilic groups in the B aromatic ring. J. Med. Chem. 2000, 43(4), 581-590. 2) Van Dort, M. E.; Robins, D. M.; Wayburn, B. Design, Synthesis, and Pharmacological Characterization of 4-[4,4-Dimethyl-3-94-hydroxybutyl]-5-oxo-2-thioxo-1-imidazolidinyl]-2-iodobenzonitrile as a High-Affinity Nonsteroidal Androgen Receptor Ligand. 2000, 43, 3344-3347.
73.9% Synthesis of (2R)-3-Bromo-N-[4-cyano-3-(trifluoromethyl) phenyl]-2-hydroxy-2- methylpropanamide. Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C) of 6 (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2- cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at room temperature. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2 X 400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 X 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2ZEtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2R)-3- Bromo-N-[4-cyano-3-(trifluoromethyl) phenyl] -2-hydroxy-2-methylpropanamide as a light- yellow solid. 1H NMR (CDC13/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1eta, OH), 3.63 (d, / = 10.8 Hz, IH, CH2), 4.05 (d, / = 10.8 Hz, IH, CH2J, 7.85 (d, / = 8.4 Hz, IH, ArH), 7.99 (dd, / = 2.1, 8.4 Hz, IH, ArH), 8.12 (d, / = 2.1 Hz, IH, ArH), 9.04 (bs, 1eta, NH). Calculated Mass: 349.99, [M-H]- 349.0. M.p.: 124-126 0C.
73.9% Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C.) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2*400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2*300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized fromCH2Cl2/hexane to give 55.8 g (73.9%) of (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide as a light-yellow solid.
73.9% [003 19j Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 mm under the same condition. After 20mm, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H20, extracted with EtOAc (2 x400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 x 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure togive a solid which was purified from column chromatography using CH2CWEtOAc (80:20) to give a solid. This solid was recrystallized from CH2CWhexane to give 55.8 g (73.9%) of (2R)-3-bromo- N-[4-cyano-3 -(trifluoromethyl)phenylj -2-hydroxy-2-methylpropanamide as a light-yellow solid. Mp 134.0-136.5C;[00320j ?H NMR (CDC13fFMS) oe 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J= 10.8 Hz, 1H,CH2), 4.05 (d, J= 10.8 Hz, 1H, CH2), 7.85 (d, J= 8.4 Hz, 1H, Ar]), 7.99 (dd, J=2.1, 8.4 Hz, 1H,ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). MS (ESI) 349.0 [M - Hj M.p.: 124- 126C.
73.9% Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (4) (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2 × 400 mL). The combined organic extracts were washed with saturated NaHCO3solution (2 × 300 mL) and brine (300 mL). The organic layer was dried over MgSO4and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from to give 55.8 g (73.9%) of (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]- 2-hydroxy-2-methylpropanamide (8) as a light-yellow solid. M.p. 134.0-136.5C;1H NMR (CDCl3/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J = 10.8 Hz, 1H, CH2), 4.05 (d, J = 10.8 Hz, 1H, CH2), 7.85 (d, J = 8.4 Hz, 1H, ArH), 7.99 (dd, J = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). Calculated Mass: 349.99, [M - H] - 349.0.
73.9% (2 ?)-3-Bromo-N-[4-cyano-3-(trifluoromethyl)phenyll-2-hydroxy-2-methylpropanamide (8) (0668) [00308] Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of ( ?)-3-bromo-2-hydroxy-2-methylpropanoic acid (4, 51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5- amino-2-cyanobenzotrifluoride (6, 40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H20, and extracted with EtOAc (2 x400 mL). The combined organic extracts were washed with saturated NaHC03 solution (2 x 300 mL) and brine (300 mL). The organic layer was dried over MgS04 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2 EtOAc (80:20) to give a solid. This solid was recrystallized from Cl hCh/hexane to give 55.8 g (73.9%) of (2K)-3-bromo- V-[4-cyano-3- (trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide as a light- yellow solid. (0669) lU NMR (CDCb/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, IH, OH), 3.63 (d, J = 10.8 Hz, IH, CH2), 4.05 (d, = 10.8 Hz, IH, CH2), 7.85 (d, = 8.4 Hz, IH, ArH), 7.99 (dd, J = 2.1, 8.4 Hz, IH, ArH), 8.12 (d, = 2.1 Hz, IH, ArH), 9.04 (bs, 1Eta, NH). MS (ESI) 349.0 [M - Eta] mp 124-126C.
73.9% Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (4, 51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5- amino-2-cyanobenzotrifluoride (6, 40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, and extracted with EtOAc (2 ×400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 × 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2R)-3-bromo-N-[4-cyano-3- (trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide as a light-yellow solid.1H NMR (CDCl3/TMS) d 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J = 10.8 Hz, 1H, CH2), 4.05 (d, J = 10.8 Hz, 1H, CH2), 7.85 (d, J = 8.4 Hz, 1H, ArH), 7.99 (dd, J = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). MS (ESI) 349.0 [M - H] -; mp 124-126C.
59% Thionyl chloride (2.4 ml, 33.6 mmol) was added dropwise to (R)-3-bromo-2-hydroxy-2-methylpropionic acid (5.11).Gram, 28 mmol) in a solution of 30 ml of THF,The temperature of the drop is controlled at 0-12 C.It takes 10 minutes.The resulting mixture was stirred under the same conditions for 2 hours.The internal temperature was adjusted to about -5 C, and triethylamine (Et3N) (5.0 ml, 36.4 mmol, 1.3 eq) was slowly added to the reaction mixture, and the internal temperature was lower than 12 C during the addition.Stir for 20 minutes under the same reaction conditions.Then, a solution of 4-cyano-3-trifluoromethyl-phenylamine (4.0 g, 21 mmol) in 40 mL of THF was added dropwise, and the mixture was stirred at 50 C for two hours.The reaction solution was cooled to 20 ± 5 C, then water (15 ml, 2.9 vol) and toluene (20 ml, 4.0 vol) was added, and after stirring, the mixture was separated and the organic phase was washed with water (15 ml, 2.9 vol.). After the combination, it was concentrated to 5 ± 0.5 volume (6.4% by weight) by distillation under reduced pressure, and the temperature was kept below 50 C during the distillation. Add toluene (31 ml, 6 volumes) to the concentrate, dilute to 5 ± 0.5 volume (6.4 wt), adjust the temperature to 2.5 ± 2.5 C, stir at this temperature for one hour, add seed crystal (0.018 g, 0.005 wt) Stirring was continued for one hour, filtered, and the filter cake was washed twice with toluene (8.5 ml each time, 1.7 volumes each time). The batch is then dried in a vacuum oven.Get 5.8 grams(R)-3-Bromo-N-(4-cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methylpropanamide.Yield 59%, HPLC (mobile phase is water and acetonitrile) purity 99% (220 nm), 99% (254 nm), optical HPLC purity 99%.

  • 6
  • [ 946825-98-5 ]
  • [ 654-70-6 ]
  • 4-[(6-cyclopentyl-2-methyl-3-oxo-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-9-yl)amino]-2-(trifluoromethyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% 10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 157 mg, 0.56 mmol), 4-amino-2-methyl-benzonitrile (Aldrich, 95 mg, 0.51 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27 mg, 0.05 mmol) were dissolved in 1,4-dioxane (7.5 mL). Caesium carbonate (330 mg, 1.01 mmol) was added and the mixture purged with a stream of nitrogen for 5 minutes. Tris(dibenzylideneacetone) palladium (II) (28 mg, 0.03 mmol) was added and the apparatus was evacuated and backfilled with nitrogen (×3) and then heated at 100 C. for 8 h. The mixture was cooled, filtered and the filtrate absorbed onto an SCX-3 column, washed with methanol and the product eluted with ammonia in methanol. Product containing fractions were concentrated and purified by preparative reverse phase chromatography to give the title compound as a white solid. (21 mg, 10%)1H NMR (399.9 MHz, DMSO-d6) delta1.57-1.72 (6H, m), 1.92-2.00 (2H, m), 2.61 (2H, m), 3.19 (3H, s), 3.64-3.66 (2H, m), 4.82-4.90 (1H, m), 7.99-8.07 (2H, m), 8.16 (1H, s), 8.50 (1H, d), 10.15 (1H, s); MS m/z 431 [M+H]+.
  • 7
  • [ 874009-75-3 ]
  • [ 654-70-6 ]
  • [ 1003838-18-3 ]
YieldReaction ConditionsOperation in experiment
<strong>[654-70-6]4-cyano-3-trifluoromethyl-aniline</strong> is reacted with propene-2-sulfonyl chloride (51), and subjected to epoxidation followed by opening of the epoxide ring with p-CN-phenol in the presence of potassium carbonate to yield compound V, as presented in Figure 1 C.
  • 8
  • C12H10ClNO4 [ No CAS ]
  • [ 654-70-6 ]
  • C20H14F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
4-methylene-tetrahydro-furan-3-ol (61 ) is prepared from a starting compound 3,6-Dioxa- bicyclo[3.1.0]hexane (60) as shown in Figure I E. It is used in a Mitsunobu type reaction with p-CN- phenol (50) to form compound 62. Dihydroxylation with OsO4, followed by oxidation with NaClO4 in the presence of TEMPO radical (2,2,6,6-tetramethylpiperidinyloxy) forms acid 64. Compound 64 <n="140"/>using thionyl chloride and <strong>[654-70-6]4-cyano-3-trifluoromethyl-aniline</strong> yields compound XXl, as presented inFigure IE.
  • 9
  • [ 1003838-29-6 ]
  • [ 654-70-6 ]
  • C20H16F3N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Compound 62 is prepared as in Example 4, followed by epoxidation to yield compound 65 as presented in Figure IF. An opening of the epoxide ring with <strong>[654-70-6]4-cyano-3-trifluoromethyl-aniline</strong> yields compound XXXVI, as presented in Figure IF.
  • 10
  • [ 2170-03-8 ]
  • [ 654-70-6 ]
  • [ 1003838-30-9 ]
YieldReaction ConditionsOperation in experiment
<strong>[654-70-6]4-cyano-3-trifluoromethyl-aniline</strong> is reacted with itaconic anhydride (66) to yield intermediate 67. Further epoxidation and opening of the epoxide ring with p-CN-phenol 50 yields compound XLVI as presented in Figure IG.
  • 11
  • [ 1002-18-2 ]
  • [ 654-70-6 ]
  • [ 1011526-76-3 ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran; at 22 - 55℃; for 0.833333h; IA (10.0 g; 40.4 mmol; 1.0 equiv), neat, was added via syringe to a clear amber solution of 2-trifluoromethyl-4-aminobenzonitrile (14.9 g; 80.8 mmol; 2.0 equiv) in 80 mL dry THF at 22C. A slight exotherm was observed. The homogeneous amber solution was stirred for 20 min, and then placed in a 55C oil <n="57"/>bath for 30 min. HPLC indicated only a small amount of aniline was present. The contents of the reactor were concentrated in vacuo to yield a tan solid. After absorption onto silica, the crude material was purified by flash column chromatography (1% acetone/CH2Cl2 to elute aniline, then 10-50% acetone/CH2Cl2 to elute desired as a pale yellow band.) to give 20.3 g (94 %) of IB as an off-white solid. HPLC: 95% at 3.736 min (retention time) (YMC ODS-A column 4.6 x 50 mm eluting with 10-90% aqueous MeOH over 4 min containing 0.1% H3PO4, 4 mL/min, monitoring at 220 nm).
94% In tetrahydrofuran; at 22 - 55℃; for 0.833333h; To a clear amber solution of 2-trifluoromethyl 4-aminobenzonitrile (14.9 g; 80.8 mmol; 2.0 equiv) in 80 mL dry THF at 22C was added Compound IA (10.0 g; 40.4 mmol; 1.0 equiv), neat, by syringe. A slight exotherm was observed. The homogeneous amber solution stirred for 20 minutes, then placed in a 55C oil bath for 30 minutes. HPLC indicated only a small amount of aniline was present. The contents of the reactor were concentrated in vacuo, yielding a tan solid. After absorption onto silica, the crude material was purified by flash column chromatography (1% acetone/DCM to elute aniline, then 10-50% acetone/DCM to elute desired as a pale yellow band.) 20.3 g (94 %) of Compound IB was obtained as an off-white solid.[00153] 95% at 3.736 min (retention times) (YMC ODS-A column 4.6 x 50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% H3PO4, 4 mL/min, monitoring at 220 nm).
  • 12
  • [ 654-70-6 ]
  • [ 5704-66-5 ]
  • [ 87310-69-8 ]
  • 13
  • [ 75-44-5 ]
  • [ 654-70-6 ]
  • [ 143782-18-7 ]
YieldReaction ConditionsOperation in experiment
In toluene; acetonitrile; at 70℃; 1) Preparation of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile (1.1) Compound 1.1 can be prepared by process "A". To this end, 14.74 g (79.21 mmol) of <strong>[654-70-6]4-amino-2-trifluoromethylbenzonitrile</strong> were dissolved in 200 ml of dry acetonitrile. This solution was added dropwise with stirring to a 20% solution, heated to 70 C., of phosgene in toluene and then stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, and the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 150 ml of dry acetonitrile and the solution was admixed with 15.5 g (79.21 mmol) of tert-butyl 2-amino-2-methylpropionate hydrochloride with stirring. 12.02 g (118.8 mmol) of triethylamine were slowly added dropwise to the reaction mixture which was then stirred at room temperature for 45 min. Thereafter, the mixture was admixed cautiously with 50 ml of concentrated hydrochloric acid and stirred at 70 C. for 1 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was admixed with ethyl acetate and water. The organic phase was removed, washed with saturated sodium carbonate solution and then with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 2:1 heptane/ethyl acetate. 21.2 g (90% yield) of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 1.1 with the melting point of 208-211 C. were obtained. ; 1) Preparation of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile (28.1) Compound 28.1 can be prepared by process "A". To this end, 5.3 ml of phosgene solution (20% in toluene) were initially charged under argon atmosphere. At 75 C., a solution of 4-cyano-3-trifluoromethylaniline in 15 ml of dry acetonitrile was slowly added dropwise. After the addition had ended, the mixture was stirred at 75 C. for another 90 min. The mixture was concentrated under reduced pressure. The residue was then taken up repeatedly in toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 15 ml of dry tetrahydrofuran, admixed with 0.72 g of 1-amino-1-cyclohexanecarboxylic acid and dropwise with 1.05 ml of triethylamine, and the mixture was stirred at room temperature for 2 h. After standing overnight at room temperature, the reaction mixture was admixed with 5 ml of concentrated hydrochloric acid and stirred under reflux for 2 h. The cooled reaction mixture was admixed with saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. 0.62 g of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile (28.1) was obtained. 1H NMR: 9.21, s, 1H, 8.30, d, 1H, 8.19, s, 1H, 8.02, d, 1H, 1.8-1.5, m, 9H, 1.4-1.25, m, 1H.
In ethyl acetate; toluene; at 0 - 20℃; for 3.5h;Heating / reflux; 4-Isocyanato-2-trifluoromethyl-benzonitrile (8a) To a solution of 5-amino-2-cyanobenzotrifluoride (1a) (2.0 g, 10.7 mmol) in ethyl acetate (6 mL) at 0 C. under argon, was added dropwise a 2.0 M solution of phosgene in toluene (6.5 mL, 12.9 mmol). The solution was stirred 30 min at 0 C. and allowed to return at room temperature. Toluene (3 mL) was then added to the ethyl acetate and the resulting solution was refluxed for 3 hrs using a Dean-Stark apparatus, equipped with an HCl trap (solid NaOH). The first 6 mL of distilled solvent was removed and replaced by toluene (6 mL). The solution was then filtrated and evaporated to give compound 8a (1.6 g) as an orange oil which was directly used for the next step. IR: 2268 (strong), 2232 (weak) cm-1.
In acetonitrile; at 70℃; 1) Preparation of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethyl-benzonitrile (1.1); Compound 1.1 can be prepared by method ?N-A?. To this end, 14.74 g (79.21 mmol) of <strong>[654-70-6]4-amino-2-trifluoromethylbenzonitrile</strong> were dissolved in 200 ml of dry acetonitrile. This solution was added dropwise with stirring to a 20% solution, heated to 70 C., of phosgene in toluene and then stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 150 ml of dry acetonitrile and the solution was admixed with stirring with 15.5 g (79.21 mmol) of tert-butyl 2-amino-2-methylpropionate hydrochloride. 12.02 g (118.8 mmol) of triethylamine were slowly added dropwise to the reaction mixture which was then stirred at room temperature for 45 min. Thereafter, the mixture was admixed cautiously with 50 ml of concentrated hydrochloric acid and stirred at 70 C. for 1 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was admixed with ethyl acetate and water. The organic phase was removed, washed with saturated sodium hydrogencarbonate solution and then with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically using silica gel with 2:1 heptane/ethyl acetate. This afforded 21.2 g (90% yield) of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 1.1 with melting point 208-211 C.
In toluene; acetonitrile; at 70℃;Product distribution / selectivity; 1.47 g (7.9 mmol) of <strong>[654-70-6]4-amino-2-trifluoromethylbenzonitrile</strong> were dissolved in 20 ml of dry acetonitrile. This solution was added dropwise with stiffing to a 20% solution, heated to 70 C., of phosgene in toluene and then the mixture was stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, and the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in acetonitrile and reacted with the amino acid ester 1.1 as described in example 1, step 3, to give 4-[3-(2-benzylbenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoro-methylbenzonitrile. The compound of example 88 can be prepared by a further method, by alkylation of the previously prepared imidazolidine-2,4-dione 88.1:
In ethyl acetate; toluene; at 0 - 5℃; for 0.5h; 1) Preparation of 4-(4,4-dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile (1.1):The compound 1.1 can be prepared by process ?A?. A solution of 10 g of 4-cyano-3-trifluoromethylaniline (described in European Patent No. 0,002,892) in 30 ml of ethyl acetate was added at from 0 to 5 C. to 33.6 ml of a toluene solution containing 1.93 M /l of phosgene, and, after stirring at from 0 to 5 C. for 30 minutes, the temperature was increased to 25 C. The mixture was distilled while fresh toluene was introduced, which was kept at a constant height, in order to compensate for the distilled volume of toluene, until a temperature of about 110 C. had been attained. The mixture was kept at reflux, until the release of hydrogen chloride decreased (4½ hours). The temperature returned to room temperature, and the white solid was dried over sodium sulfate and rinsed 3 times with toluene. The organic phase was concentrated to dryness under reduced pressure, heated at 60 C. for one hour and then cooled under argon, in order to obtain 11.6 g of 4-isocyanato-2-trifluoromethylbenzonitrile.A solution of 6.6 g of 4-isocyanato-2-trifluoromethylbenzonitrile in 10 ml of dichloroethane was added at 5 C. to a solution of 2.63 g of 2-amino-2-cyanopropane and 36 ml of dichloroethane and 0.9 ml of triethylamine, and, after stirring at room temperature for 16 hours, the mixture was concentrated to dryness. The 7.7 g of residue were chromatographed on silica gel and eluted with an 85-15 methylene chloride-acetone mixture, in order to obtain 3.54 g of the desired product, which melts at 228 C. An analysis sample was prepared by crystallizing 300 mg from isopropanol, in order to obtain 267 mg of the product, which melts at 228 C.
With sodium hydrogencarbonate; In dichloromethane; toluene; at 0 - 20℃; for 2h; Preparation of Compound 34A suspension of 4-cyano-3-trifluomethylaniline (27) (2.01 g, 10.8 mmol) and sodium bicarbonate (2.25 g, 26.8 mmol) in dichloromethane (50 mL) was cooled at 0 C., slowly treated with a 20% phosgene solution in toluene (11 mL, 20.9 mmol) and stirred for 2 h after removing the ice-water bath. The reaction mixture was filtered and concentrated under reduced pressure. The crude isocyanate 34 was used in the next step without further purification.

  • 16
  • [ 928312-10-1 ]
  • [ 654-70-6 ]
  • C19H17F3N2O3 [ No CAS ]
  • 17
  • [ 928312-10-1 ]
  • [ 654-70-6 ]
  • [ 108-24-7 ]
  • [ 97760-99-1 ]
  • [ 928312-11-2 ]
  • 18
  • [ 4390-96-9 ]
  • [ 654-70-6 ]
  • [ 888071-25-8 ]
  • 19
  • [ 654-70-6 ]
  • [ 78450-85-8 ]
  • [ 888071-26-9 ]
  • 20
  • [ 654-70-6 ]
  • [ 888073-09-4 ]
  • 4-amino-3,5-dichloro-2-trifluoromethyl-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide; In methanol; at 0℃; for 2h; Example 151; 4-Amino-5-chloro-2-trifluoromethyl-benzonitrile and 4-Amino-3.5-dichloro-2-trifluoromethyl-benzonitrile; 4-Amino-2-trifluoromethyl-benzonitrile (10.5 mmoL) , NCS (15.5 mmoL) in MeOH (50 ml_) at O0C was stirred for 2 hrs. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with sodium thiosulfate, water and brine, then dried over anhydrous Na2SO4, filtered and concentrated to yield crude material, which was then purified by column chromatography using hexanes and ethyl acetate to yield the title compounds as brown solids. 4-Amino-5-chloro-2-trifluoromethyl-benzonitrile:H NMR (CDCI3) delta 7.65 (s, 1 H), 7.02 (s, 1 H), 4.90 (br, s, 2H) MS (m/z): MH+ 221.4-Amino-3,5-dichloro-2-trifluoromethyl-benzonitrile: 1H NMR (CDCI3) delta 7.61 (s, 1 H), 5.32 (br, s, 2H) MS (m/z): MH+ 256. EPO <DP n="173"/>
  • 21
  • [ 654-70-6 ]
  • [ 90715-73-4 ]
  • [ 888072-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3,3,3-trifluoro-2-hydroxymethyl-propionamide [ No CAS ]
  • 22
  • [ 654-70-6 ]
  • [ 101066-87-9 ]
YieldReaction ConditionsOperation in experiment
62.5% With sulfuric acid; potassium iodide; sodium nitrite; In water; acetonitrile; at 20℃; A solution of 4-amino-2-chlorobenzonitrile (10) (1.6g,10.5 mmol) in MeCN (60.0 ml) and water (18.0 ml) was cooled to0 C. Sulfuric acid (1.8 ml) and 2.0M aqueous sodium nitrite(840.0 mg, 6.0 ml) was slowly added, respectively. Thereafter potassiumiodide (3.3 g, 20.0 mmol) dissolved in 5.0 ml of water wasadded dropwise. The reaction mixture was allowed to warm up toroom temperature and stirred overnight. The organic phase wasevaporated, the resulting suspension was dissolved in ethyl acetateand washed three times with 10% aqueous NaHSO3. The organicphase was dried over anhydrous Na2SO4, filtered and concentratedunder vacuum. Purification on silica using a solvent of 10% ethylacetate in hexanes yielded the intermediate 12 as a white solid(1.71 g, yield 62.5%).
  • 23
  • [ 654-70-6 ]
  • 3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid (2-chloro-4-cyano-5-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 24
  • [ 654-70-6 ]
  • C14H9ClF6N4O [ No CAS ]
  • 25
  • [ 654-70-6 ]
  • [ 888073-11-8 ]
  • 28
  • [ 654-70-6 ]
  • C15H14F3N3O4 [ No CAS ]
  • 29
  • [ 654-70-6 ]
  • C14H10F3N3O3 [ No CAS ]
  • 35
  • [ 654-70-6 ]
  • 2-(1-hydroxy-1-methyl-ethyl)-3-methyl-6-trifluoromethyl-1<i>H</i>-indole-5-carbonitrile [ No CAS ]
  • 38
  • [ 654-70-6 ]
  • C10H8F3IN2O4S2 [ No CAS ]
  • 39
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3-methyl-3,4-dihydro-2H-pyrazole-3-carboximidothioic acid ethyl ester [ No CAS ]
  • 40
  • [ 654-70-6 ]
  • 4-(6-amino-3a-methyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile [ No CAS ]
  • 42
  • [ 654-70-6 ]
  • 2-(1-hydroxy-1-methyl-2-phenylsulfanyl-ethyl)-6-trifluoromethyl-1<i>H</i>-indole-5-carbonitrile [ No CAS ]
  • 49
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxamidine [ No CAS ]
  • 50
  • [ 654-70-6 ]
  • benzoic acid 2-(5-cyano-6-trifluoromethyl-1<i>H</i>-indol-2-yl)-2-hydroxy-propyl ester [ No CAS ]
  • 53
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3,N'-dimethyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxamidine [ No CAS ]
  • 55
  • [ 654-70-6 ]
  • 2-[2-(4-chloro-phenylsulfanyl)-1-hydroxy-1-methyl-ethyl]-6-trifluoromethyl-1<i>H</i>-indole-5-carbonitrile [ No CAS ]
  • 56
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-N'-hydroxy-3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxamidine [ No CAS ]
  • 57
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboximidothioic acid ethyl ester [ No CAS ]
  • 58
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-N'-methoxy-3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxamidine [ No CAS ]
  • 59
  • [ 654-70-6 ]
  • 5-[(4-cyano-3-trifluoromethyl-phenylimino)-ethylsulfanyl-methyl]-5-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]
  • 60
  • [ 654-70-6 ]
  • 2-[2-(4-fluoro-benzenesulfonyl)-1-hydroxy-1-methyl-ethyl]-6-trifluoromethyl-1<i>H</i>-indole-5-carbonitrile [ No CAS ]
  • 61
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-N'-ethyl-3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxamidine [ No CAS ]
  • 62
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3(R)-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboximidothioic acid ethyl ester [ No CAS ]
  • 63
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3(S)-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboximidothioic acid ethyl ester [ No CAS ]
  • 64
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3-ethyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboximidothioic acid ethyl ester [ No CAS ]
  • 65
  • [ 654-70-6 ]
  • 4-fluoro-benzoic acid 2-(5-cyano-6-trifluoromethyl-1<i>H</i>-indol-2-yl)-2-hydroxy-propyl ester [ No CAS ]
  • 66
  • [ 654-70-6 ]
  • 4-(6-imino-3a-methyl-2-trifluoromethyl-3,3a-dihydro-pyrazolo[1,5-c]oxazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile [ No CAS ]
  • 68
  • [ 654-70-6 ]
  • N-[(4-cyano-3-trifluoromethyl-phenylimino)-(3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-yl)-methyl]-methanesulfonamide [ No CAS ]
  • 69
  • [ 654-70-6 ]
  • N'-(4-cyano-3-trifluoromethyl-phenyl)-N,N-diethyl-3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carboxamidine [ No CAS ]
  • 70
  • [ 654-70-6 ]
  • 6-amino-4-(4-cyano-3-trifluoromethyl-phenylimino)-3a-methyl-3a,4-dihydro-3H-imidazo[1,5-b]pyrazole-2-carboxylic acid ethyl ester [ No CAS ]
  • 73
  • [ 654-70-6 ]
  • 4-(6-amino-3a-ethyl-2-trifluoromethyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile [ No CAS ]
  • 74
  • [ 654-70-6 ]
  • 4-[(3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-yl)-pyrrolidin-1-yl-methylene]-amino}-2-trifluoromethyl-benzonitrile [ No CAS ]
  • 75
  • [ 654-70-6 ]
  • N-[4-(4-cyano-3-trifluoromethyl-phenylamino)-3aR-methyl-2-trifluoromethyl-3a,4-dihydro-3H-imidazo[1,5-b]pyrazol-6-yl]-2,2,2-trifluoro-acetamide [ No CAS ]
  • 78
  • [ 654-70-6 ]
  • N-(4-cyano-3-trifluoromethyl-phenyl)-3-methyl-5-pentafluorophenyl-3,4-dihydro-2H-pyrazole-3-carboximidothioic acid ethyl ester [ No CAS ]
  • 79
  • [ 654-70-6 ]
  • 4-(6-amino-3a-methyl-2-pentafluorophenyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile [ No CAS ]
  • 81
  • [ 654-70-6 ]
  • [ 897364-32-8 ]
  • 83
  • [ 654-70-6 ]
  • 4-piperidin-4-yl-2-trifluoromethyl-benzonitrile [ No CAS ]
  • 84
  • [ 654-70-6 ]
  • [ 854765-35-8 ]
  • 85
  • [ 654-70-6 ]
  • 4'-cyano-3'-trifluoromethyl-biphenyl-4-carbonyl chloride [ No CAS ]
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