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[ CAS No. 654-99-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 654-99-9
Chemical Structure| 654-99-9
Chemical Structure| 654-99-9
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Product Details of [ 654-99-9 ]

CAS No. :654-99-9 MDL No. :MFCD00083521
Formula : C8H4F4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BRFNBGWEOKQIND-UHFFFAOYSA-N
M.W : 208.11 Pubchem ID :688294
Synonyms :

Calculated chemistry of [ 654-99-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.36
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 4.12
Log Po/w (MLOGP) : 3.09
Log Po/w (SILICOS-IT) : 2.69
Consensus Log Po/w : 2.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.85
Solubility : 0.296 mg/ml ; 0.00142 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.29 mg/ml ; 0.00139 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.237 mg/ml ; 0.00114 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 654-99-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 654-99-9 ]

* 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 [ 654-99-9 ]

[ 654-99-9 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 425-75-2 ]
  • [ 654-99-9 ]
  • 5-Fluoro-4-nitro-2-trifluoromethyl-benzoic acid ethyl ester [ No CAS ]
  • 3-Fluoro-2-nitro-6-trifluoromethyl-benzoic acid ethyl ester [ No CAS ]
  • 2
  • [ 654-99-9 ]
  • 3-Fluoro-2-nitro-6-trifluoromethyl-benzoic acid [ No CAS ]
  • 5-Fluoro-4-nitro-2-trifluoromethyl-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Oakwood Products, Inc., 1741 Old Dunbar Road, West Columbia, S.C. 29172, USA. TCI America, 9211 N. Harborgate Street, Portland, Oreg. 97203, USA ... 4-fluoro-3-nitrobenzoic acid; 5-fluoro-2-nitrobenzoic acid; 2-fluoro-3-(trifluoromethyl)benzoic acid; 4-fluoro-3-(trifluoromethyl)benzoic acid; 5-fluoro-2-(trifluoromethyl)benzoic acid; 2-hydroxy-3-isopropyl-benzoic acid; 3-iodobenzoic acid; 5-iodosalicylic acid; ...
  • 4
  • [ 654-99-9 ]
  • [ 104800-02-4 ]
  • [ 1130849-04-5 ]
  • 5
  • [ 654-99-9 ]
  • [ 57260-71-6 ]
  • [ 932720-83-7 ]
YieldReaction ConditionsOperation in experiment
83% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 10 - 20℃; Synthesis of 4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester HOBt (163 mg, 1.2 mmol) and DIEA (373 mg, 2.9 mmol) were added to a stirred solution of <strong>[654-99-9]5-fluoro-2-trifluoromethyl-benzoic acid</strong> (200 mg, 0.9 mmol) in DMF (1.0 mL) and the resulting mixture was cooled to 10 C. EDCI.HCl (231 mg, 1.2 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (197 mg, 1.0 mmol) were then added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and the product extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude residue, which was purified by column chromatography using silica gel 60-120 mesh (30% ethyl acetate in hexane) to afford 301 mg (83%) of 4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester, LCMS purity: 99.5%.
  • 6
  • [ 654-99-9 ]
  • [ 4755-77-5 ]
  • [ 1232028-62-4 ]
YieldReaction ConditionsOperation in experiment
91.4% With triethylamine; In dichloromethane; at 20℃; for 1h; Step 1 [4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-oxo-acetic acid ethyl ester Chloro-oxo-acetic acid ethyl ester (480 mg, 3.51 mmol) was added a cold (0 C.) mixture of 5-Fluoro-2-trifluoromethyl-phenyl)-piperazin-1-yl-methanone hydrochloride salt (1.0 g, 3.2 mmol) prepared by the similar method as described in earlier example using 5-fluoro-2-trifluoromethyl benzoic acid as starting material, Aldrich, St. Louis, Mo.), Et3N (809 mg, 1.1 mL, 8.0 mmol) in DCM (10 mL) and stirring was continued at ambient temperature for 1 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed the organic layer with brine solution, dried over Na2SO4, and concentrated under reduced pressure to afford 1.1 g (91.4%) of [4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-oxo-acetic acid ethyl ester.
  • 7
  • [ 654-99-9 ]
  • [ 129799-15-1 ]
  • [ 1232028-51-1 ]
YieldReaction ConditionsOperation in experiment
85.9% Step 6 Synthesis of 4-(5-Fluoro-2-trifluoromethyl-benzoyl)-<strong>[129799-15-1]piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester</strong> DIPEA (430 mg, 0.58 mL, 3.27 mmol) followed by HOBT (121 mg, 0.9 mmol) and EDCI (230 mg, 1.22 mmol) were added to a stirred solution of 5-Fluoro-2-trifluoromethyl-benzoic acid (170 mg, 0.82 mmol) in DMF (2.0 mL) at room temperature. After 2 minutes 2 minutes <strong>[129799-15-1]piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester</strong> (200 mg, 0.82 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated to afford 305 mg (85.9%) of 4-(5-Fluoro-2-trifluoromethyl-benzoyl)-<strong>[129799-15-1]piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester</strong>.
  • 8
  • [ 654-99-9 ]
  • 5-fluoro-2-(trifluoromethyl)benzoyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 0.5h; Step 3 Synthesis of 1-(5-Fluoro-2-trifluoromethyl-benzoyl)-4-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperazine-2-carboxylic acid methyl ester Oxalyl chloride (67 mg, 0.53 mmol) was added to an ice cold (0 C.) solution of 5-Fluoro-2-trifluoromethyl-benzoic acid (91 mg, 0.44 mmol) in DCM (3 mL) followed by 1 drop of DMF and stirred at ambient temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure to afford the residue. The residue obtained was diluted with DCM (3 mL) and added to a cold (0 C.) mixture of 4-{2-[(5-Phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperazine-2-carboxylic acid methyl ester (180 mg, 0.44 mmol), DIPEA (171 mg, 0.23 mL, 1.32 mmol) in DCM (4 mL) and stirred at ambient temperature for 1 hr. The reaction mass was diluted with DCM, washed the organic layer with water followed by brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 200 mg(80.74%) of 1-(5-Fluoro-2-trifluoromethyl-benzoyl)-4-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperazine-2-carboxylic acid methyl ester.
With dmap; oxalyl dichloride; In dichloromethane; at 50℃; for 0.666667h; Oxalyl chloride (1.23 ml, 14.24 mmol) was added dropwise to a solution of <strong>[654-99-9]5-fluoro 2-trifluoromethyl benzoic acid</strong> (1 gm, 4.81 mmol) in HPLC grade DCM(15 ml), containing DMAP. The reaction mixture was heated to 50 C. for 40 min. The reaction mass was cooled to room temperature and solvent evaporated to dryness under a nitrogen atmosphere to get crude 5-fluoro 2-trifluoromethyl benzoyl chloride.
  • 9
  • 5-phenyl-1H-pyrazole-3-carboxylic acid [2-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-2-oxo-ethyl]-amide hydrochloride [ No CAS ]
  • [ 654-99-9 ]
  • [ 1232028-16-8 ]
YieldReaction ConditionsOperation in experiment
23% Step 3 Synthesis of 5-Phenyl-1H-pyrazole-3-carboxylic acid {2-[5-(5-fluoro-2-trifluoromethyl-benzoyl)-2,5-diaza-bicyclo[2.2.1]hept-2-yl]-2-oxo-ethyl}-amide DIPEA (103 mg, 0.14 mL, 0.8 mmol) was added to a stirred solution of <strong>[654-99-9]5-fluoro-2-trifluoromethyl-benzoic acid</strong> (41.6 mg, 0.2 mmol) in DMF (3 mL). HOBT (29.7 mg, 0.22 mmol) and EDCI (76.6 mg, 0.4 mmol) were then added at room temperature. After 2 minutes, 5-phenyl-1H-pyrazole-3-carboxylic acid [2-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-2-oxo-ethyl]amide hydrochloride (70 mg, 0.2 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added. The product was extracted with ethyl acetate and the organic layer was washed with saturated brine solution then dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the resulting residue was purified by column chromatography (using 60-120 silica gel and 60% ethyl acetate in hexane as eluent) to afford 24 mg (23%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[5-(5-fluoro-2-trifluoromethyl-benzoyl)-2,5-diaza-bicyclo[2.2.1]hept-2-yl]-2-oxo-ethyl}-amide. LCMS Purity: 96.11%. 1H NMR (DMSO-d6): delta 13.7 (s, 2H), 8.6 (s, 1H), 8.2 (m, 1H), 8.1 (m, 1H), 8.0-7.85 (m, 2H), 7.85-7.7 (m, 4H), 7.7-7.6 (m, 1H), 7.6-7.3 (m, 8H), 7.1 (d, 1H), 6.6-6.5 (s, 1H), 5.0-4.7 (m, 3H), 4.2-3.9 (m, 5H), 3.7-3.4 (m, 5H), 3.0 (m, 1H), 2.0-1.4 (m, 4H).
  • 10
  • [ 654-99-9 ]
  • [ 18107-18-1 ]
  • [ 773873-90-8 ]
YieldReaction ConditionsOperation in experiment
In methanol; diethyl ether; chloroform; for 1h; To a solution of <strong>[654-99-9]5-fluoro-2-(trifluoromethyl)benzoic acid</strong> (2.0 g, 9.62 mmol, Aldrich) in a mixture of chloroform and methanol (1 :1 , 40 ml) was added a 2 M solution of TMS- diazomethane in ether (approximately 8 ml) dropwise, in portions over about 1 h, allowing the solution to cool down between additions. The solution was evaporated in vacuo. To the residue was added chloroform (approximately 40 ml) and the solvent removed in vacuo to give methyl 5-fluoro-2-(trifluoromethyl)benzoate as a colourless slightly cloudy oil (2.09 g).
  • 11
  • [ 64-17-5 ]
  • [ 654-99-9 ]
  • [ 773135-32-3 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride;Reflux; (d) 5-Fluoro-2-trifluoromethyl-benzoic acid ethyl esterA mixture of <strong>[654-99-9]5-fluoro-2-trifluoromethyl-benzoic acid</strong> (3.0 g; 10 mmol) and 25 mL HCI in EtOH was heated at reflux over night. The mixture was cooled to rt and evaporated i.vac.Yield: 2,47g (73%); MS [M+H]+ = 236; TLC (RP8; MeOH: 5%NaCI-Lsg 6/4) Rf= 0,16
73% With hydrogenchloride;Reflux; A mixture of <strong>[654-99-9]5-fluoro-2-trifluoromethyl-benzoic acid</strong> (3.0 g; 10 mmol) and 25 mL HCl in EtOH was heated at reflux over night. The mixture was cooled to rt and evaporated i.vac.Yield: 2.47 g (73%); MS [M+H]+=236; TLC (RPB; MeOH: 5% NaCl-Lsg 6/4) Rf=0.16
  • 12
  • [ 654-99-9 ]
  • [ 1294496-79-9 ]
  • 13
  • [ 654-99-9 ]
  • [ 1294494-79-3 ]
  • 14
  • [ 654-99-9 ]
  • [ 1294496-76-6 ]
  • 15
  • [ 654-99-9 ]
  • [ 1294496-77-7 ]
  • 16
  • [ 654-99-9 ]
  • [ 1294496-78-8 ]
  • 17
  • [ 110-91-8 ]
  • [ 654-99-9 ]
  • [ 124-41-4 ]
  • [ 1441207-87-9 ]
YieldReaction ConditionsOperation in experiment
4% To <strong>[654-99-9]5-fluoro-2-(trifluoromethyl)benzoic acid</strong> (1 g, 4.8 mmol) in concentrated sulphuric acid (5 mL) at 0C was carefully added concentrated nitric acid (5 mL) dropwise. The mixture was heated to 100C for 18 h. The cooled mixture was poured into an ice/water mixture (75 mL) and then extracted with EtOAc (75 mL). The organic layer was washed with brine (75 mL) and passed through a hydrophobic frit. The solvent was removed in vacuo and half of the residue was added to a solution of sodium methoxide in THF [formed by the addition of sodium hydride (220 mg, 60% in oil, 5.5 mmol) to a mixture of THF (5 mL) and methanol (0.12 mL, 2.9 mmol)]. The mixture was stirred at RT for 3 h and then DCM (20 mL) and aqueous 2 M HC1 (5 mL) were added. The mixture was passed through a hydrophobic frit and the solvent was removed in vacuo. The residue was dissolved in DCM (24 mL) and then DIPEA (0.48 mL, 7.2 mmol) and HATU (1.1 g, 2.9 mmol) were added, followed by morpholine (0.15 mL, 2.9 mmol). The mixture was allowed to stir at RT for 4 h and then saturated aqueous sodium bicarbonate solution (25 mL) was added. The mixture was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-10% EtOAc in iso-hexane) gave (5-methoxy-4-nitro-2- (trifluoromethyl)phenyl)(mo holino)methanone (350 mg, 4%) as a yellow solid. LCMS (lOcm ESCI Bicarb MeCN): [M + H]+ = 335 at 3.33 min. ? NMR (400 MHz, CDC13): delta 8.21 (s, 1H), 7.02 (s, 1H), 4.04 (s, 3H), 3.96-3.59 (m, 4H), 3.64-3.59 (m, 2H), 3.22-3.17 (m, 2H).
  • 18
  • [ 654-99-9 ]
  • [ 1441199-51-4 ]
  • 19
  • [ 654-99-9 ]
  • [ 1441199-46-7 ]
  • 20
  • [ 654-99-9 ]
  • [ 1441207-93-7 ]
  • 21
  • [ 654-99-9 ]
  • 4-(2-amino-3-methylbutanoyl)benzonitrile hydrochloride [ No CAS ]
  • N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-yl)-5-fluoro-2-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% 5-Fluoro-2-(trifluoromethyl)benzoic acid (CAS 654-99-9, 52.3 mg, 0.25 mmcl) was dissolved in DMF (1 mL). HBTU (119 mg, 0.31 mmcl) and TEA (0.088 mL, 0.63 mmcl) were added. The mixture was stirred for 15 mm at rt and then a mixture of 1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-aminium chloride (Example 49b, 50 mg, 0.21 mmcl) and TEA (0.088 mL, 0.63 mmcl) in DMF (2 mL) was added. The reaction mixture was stirred for 2 h at rt and then filtered and purified by preparative HPLC to give N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan- 2-yl)-5-fluoro-2-(trifluoromethyl)benzamide (58.0 mg, 71%).1H NMR (500 MHz, DMSO-d6) 5 ppm 0.94 (d, 3 H) 0.91 (d, 3 H) 2.14 - 2.30 (m, 1 H) 5.25 - 5.45(m, 1 H) 7.21 (dd, 1 H) 7.46 - 7.60 (m, 1 H) 7.87 (dd, 1 H) 8.00 - 8.12 (m, 2 H) 8.13 - 8.28 (m, 2 H) 9.11 (d, 1 H).MS (ESI) m/z 393 [Mi-H]
  • 22
  • [ 654-99-9 ]
  • C10H7F4N5O [ No CAS ]
  • 23
  • [ 654-99-9 ]
  • [ 124-40-3 ]
  • 5-fluoro-N,N-dimethyl-2-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20℃; for 5h; (Reference Example 101) 5-Fluoro-N,N-dimethyl-2-(trifluoromethyl)benzamide[0656] 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter, referred to as EDC, 2.67 g, 13.93 mmol), 1-hydroxybenzotriazole monohydrate (140 mg, 0.91 mmol), and dimethylamine (2.0 M solution in THF, 10.0 mL, 20.0 mmol) were added at room temperature to a solution of <strong>[654-99-9]5-fluoro-2-(trifluoromethyl)benzoic acid</strong> (1.93 g, 9.27 mmol) in dichloromethane (50 mL), and the mixture was stirred at room temperature for 5 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with dichloromethane. The obtained organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 100/0 - 60/40 (gradient)] to obtain the title compound (1.32 g, yield: 61%).[0658] 1H-NMR (400 MHz, CDCl3) delta: 7.71 (1H, dd, J = 9, 5 Hz), 7.22-7.17 (1H, m), 7.06 (1H, dd, J = 8, 2 Hz), 3.13 (3H, s), 2.82 (3H, s).
61% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; at 20℃; for 5h; 5-fluoro-2- (trifluoromethyl) benzoic acid (1.93g, 9.27mmol) in dichloromethane (50 mL) solution of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter, EDC and, 2.67g, 13.93mmol), 1- hydroxybenzotriazole monohydrate (140mg, 0.91mmol), and, dimethyl amine (2.0M THF solution, 10.0mL, 20.0mmol) at room temperature in addition, the mixture was stirred at room temperature for 5 hours.The reaction mixture, a saturated aqueous solution of ammonium chloride was added, extracted with dichloromethane, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, under reduced pressure, the solvent was distilled off.The obtained residue was purified by silica gel column chromatography [elution solvent: hexane / ethyl acetate = 100 / 0-60 / 40 (gradient) gave the title compound (1.32 g, 61% yield).1
  • 24
  • [ 654-99-9 ]
  • 5-[4-(5-amino-1H-pyrazol-3-yl)piperidin-1-yl]-N,N-dimethyl-2-(trifluoromethyl)benzamide [ No CAS ]
  • 25
  • [ 654-99-9 ]
  • 1-(4,5-dimethyl-6-(1-methyl-1H-pyrazol-5-yl)pyridazin-3-yl)piperidin-4-amine trifluoroacetate [ No CAS ]
  • N-(1-(4,5-dimethyl-6-(1-methyl-1H-pyrazol-5-yl)pyridazin-3-yl)piperidin-4-yl)-5-fluoro-2-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 0 - 20℃; for 6h;Inert atmosphere; General procedure: DIPEA (0.5 mL) was added to a solution of amine (1 equiv) in dichloromethane (10 mL). The mixture was stirred at 0 C for 15 min. Then 4-fluoro-2-(trifluoromethyl)benzoic acid (1.2 equiv) and HATU (1.2 equiv) were added to the solution, the reaction mixture was stirred for 6 h while warming at room temperature. The reaction solution was washed with water and extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 30:1) to yield pure product. 5.1.3.1. (R)-N-(1-(6-Chloro-4,5-dimethylpyridazin-3-yl)pyrrolidin-3-yl)-4-fluoro-2-(trifluoromethyl)benzamide (10a). Yellow solid(76%)
  • 26
  • [ 654-99-9 ]
  • [ 2486-70-6 ]
  • 4-[5-fluoro-2-(trifluoromethyl)benzamido]-3-methylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.874 g To a solution of 5-fluoro-2-(trifluoromethyl)benzoic acid (2.54 g) in DMA (20 mL) was added SOC12 (0.933 mL), and the mixture was stirred at room temperature for 2.5 hours. LC-MS showed that the starting materials remained, and additional SOC12 (0.170 mL) was added to the mixture. Then, the mixture was stirred for 1 hour. 4-Amino-m-toluic acid (1.757 g) was added thereto, and the mixture was stirred at room temperature overnight. Then, the mixture was homogenized by addition of SN aqueous NaOH solution (20 mL) and water, and then the aqueous layer was washed with AcOEt. The aqueous layer was acidified by addition of SN HC1, and then iPr2O was added thereto. The mixture was stirred for a while, and the precipitated solid was filtered and dried at 60C to give4- [5-fluoro-2-(trifluoromethyl)benzamidoj -3-methylbenzoic acid (2.874 g).
  • 27
  • [ 654-99-9 ]
  • 4-(3-amino-6-fluoro-7-methyl-1H-indazol-5-yl)-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dicarbonitrile [ No CAS ]
  • N-[5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-6-fluoro-7-methyl-1H-indazol-3-yl]-5-fluoro-2-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl acetamide; at 100℃; for 2h;Microwave irradiation; To a stirred solution of 4-(3-amino-6-fluoro-7-methyl-1H-indazol-5-yl)-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dicarbonitrile (200 mg, 595 pmol) in DMA (5.8 mL) was added N,N-diisopropylethylamine (410 mI, 2.4 mmol), <strong>[654-99-9]5-fluoro-2-(trifluoromethyl)benzoic acid</strong> (186 mg, 892 pmol) and HATU (362 mg, 951 mihoI). The mixture was stirred at 100C for 2 h in a microwave oven. An aqueous solution of sodium bicarbonate was added, the mixture was stirred for 15 minutes and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography followed by aminophase-silicagel chromatography gave a solid that was triturated with a mixture of dichloromethane and hexane to give 107 mg (34 % yield) of the title compound. LC-MS (Method 1 ): Rt = 1 .1 1 min; MS (ESIpos): m/z = 527 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 2.235 (16.00), 2.430 (4.75), 2.518 (0.98), 2.523 (0.66), 3.331 (10.12), 4.619 (2.09), 5.759 (2.04), 7.563 (0.40), 7.576 (1 .57), 7.594 (1 .22), 7.740 (0.68), 7.746 (0.71 ), 7.762 (0.71 ), 7.768 (0.66), 7.945 (0.69), 7.958 (0.73), 7.968 (0.67), 7.980 (0.62), 1 1 .164 (2.00), 13.080 (1.73).
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Similarity: 0.91

Chemical Structure| 1483-47-2

[ 1483-47-2 ]

2-(Trifluoromethyl)terephthalic acid

Similarity: 0.91

Chemical Structure| 42580-42-7

[ 42580-42-7 ]

2,5-Bis(trifluoromethyl)benzoic acid

Similarity: 0.91

Carboxylic Acids

Chemical Structure| 161622-05-5

[ 161622-05-5 ]

3-Fluoro-5-trifluoromethylbenzoic acid

Similarity: 0.91

Chemical Structure| 32890-87-2

[ 32890-87-2 ]

2,4-Bis(trifluoromethyl)benzoic acid

Similarity: 0.91

Chemical Structure| 433-97-6

[ 433-97-6 ]

2-(Trifluoromethyl)benzoic acid

Similarity: 0.91

Chemical Structure| 1483-47-2

[ 1483-47-2 ]

2-(Trifluoromethyl)terephthalic acid

Similarity: 0.91

Chemical Structure| 42580-42-7

[ 42580-42-7 ]

2,5-Bis(trifluoromethyl)benzoic acid

Similarity: 0.91

Trifluoromethyls

Chemical Structure| 161622-05-5

[ 161622-05-5 ]

3-Fluoro-5-trifluoromethylbenzoic acid

Similarity: 0.91

Chemical Structure| 32890-87-2

[ 32890-87-2 ]

2,4-Bis(trifluoromethyl)benzoic acid

Similarity: 0.91

Chemical Structure| 433-97-6

[ 433-97-6 ]

2-(Trifluoromethyl)benzoic acid

Similarity: 0.91

Chemical Structure| 1483-47-2

[ 1483-47-2 ]

2-(Trifluoromethyl)terephthalic acid

Similarity: 0.91

Chemical Structure| 42580-42-7

[ 42580-42-7 ]

2,5-Bis(trifluoromethyl)benzoic acid

Similarity: 0.91