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[ CAS No. 67515-74-6 ] {[proInfo.proName]}

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Product Details of [ 67515-74-6 ]

CAS No. :67515-74-6 MDL No. :MFCD00070814
Formula : C8H7F4N Boiling Point : -
Linear Structure Formula :- InChI Key :HZDVQEUISWBXPV-UHFFFAOYSA-N
M.W : 193.14 Pubchem ID :522270
Synonyms :

Calculated chemistry of [ 67515-74-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.08
TPSA : 26.02 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 3.72
Log Po/w (MLOGP) : 3.03
Log Po/w (SILICOS-IT) : 2.88
Consensus Log Po/w : 2.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.851 mg/ml ; 0.00441 mol/l
Class : Soluble
Log S (Ali) : -1.92
Solubility : 2.3 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0472 mg/ml ; 0.000244 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 67515-74-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338 UN#:1760
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 67515-74-6 ]

* 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 [ 67515-74-6 ]

[ 67515-74-6 ] Synthesis Path-Downstream   1~37

YieldReaction ConditionsOperation in experiment
Amid 12, LiAlH4;
Nitril 13, H2;
entspr.Benzamid, LiAlH4;
  • 2
  • [ 67515-74-6 ]
  • [ 311770-42-0 ]
  • [ 876296-07-0 ]
YieldReaction ConditionsOperation in experiment
With TEA; chloroformic acid ethyl ester In dichloromethane
  • 3
  • [ 512785-26-1 ]
  • [ 67515-74-6 ]
  • 5-(4-cyclohexyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid 4-fluoro-3-trifluoromethyl-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
  • 4
  • [ 75-44-5 ]
  • [ 67515-74-6 ]
  • C9H6ClF4NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene Heating / reflux; 209 N-[4-fluoro-3-(trifluoromethyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea EXAMPLE 209 N-[4-fluoro-3-(trifluoromethyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea 4-Fluoro-3-(trifluoromethyl)benzylamine (0.8 g, 4.15 mmol) in toluene (20 mL) was refluxed with 20% w/v phosgene solution in toluene (2.1 mL) overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was again taken up in toluene (25 mL) and was stirred overnight at 80° C. with DIEA (2 mL, 11.5 mmol) and 5-amino-3-methylisoquinoline (500 mg, 3.16 mmol). The mixture was cooled to room temperature, concentrated in vacuo, and the residue was purified by silica gel chromatography (97:3 CH2Cl2:CH3OH, eluant) to provide the title compound. The corresponding hydrochloride salt was prepared by treatment with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 9.18 (s, 1H), 8.72 (s, 1H), 8.16 (d, 1H, J=7.8 Hz), 7.70-7.77 (m, 4H), 7.48-7.54 (m, 3H), 7.14 (t, 1H, J=5.9 Hz), 4.42 (d, 2H, J=6.1 Hz), 2.64 (s, 3H); MS (ESI+) m/z 378 (M+H).
  • 5
  • [ 869297-03-0 ]
  • [ 67515-74-6 ]
  • ethyl 4-[({2-[([4-fluoro-3-(trifluoromethyl)phenyl]methyl}amino)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl}methyl)oxy]methyl}benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% In ethanol at 80℃; for 15h; 315 Example 315; ethyl 4-[({2-[([4-fluoro-3- (trifluoromethyl) phenyl]methyl}amino)carbonyl]-4-oxo- 3,4-dihydrothieno [2,3-d]pyrimidin-5- yl} methyl)oxy]methyl}benzoate; A suspensionof ethyl 5-[({4- [(ethyloxy) carbonyl]phenyl}methyl)oxy]methyl}-4-oxo-3,4- dihydrothieno[2,3-d]pyrimidine-2-carboxylate (0.350 g, 0.840 mmol) obtained in Reference Example 158 and 1-[4- fluoro-3- (trifluoromethyl)phenyl]methanamine (0.315 g, 1.63 mmol) in ethanol (16 mL) was stirred with heating at 80°C for 15 hrs. The mixture was allowed to cool to room temperature and the precipitated solid was collected by filtration and washed with ethanol to give the title compound as a white powder (397 mg, 73%). melting point: 227-229°C
73% In ethanol at 80℃; for 15h; 315 ethyl 4-[({2-[([4-fluoro-3-(trifluoromethyl)phenyl]methyl}amino)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl}methyl)oxy]methyl}benzoate Example 315 ethyl 4-[({2-[([4-fluoro-3-(trifluoromethyl)phenyl]methyl}amino)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl}methyl)oxy]methyl}benzoate A suspension of ethyl 5-[({4-[(ethyloxy)carbonyl]phenyl}methyl)oxy]methyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (0.350 g, 0.840 mmol) obtained in Reference Example 158 and 1-[4-fluoro-3-(trifluoromethyl)phenyl]methanamine (0.315 g, 1.63 mmol) in ethanol (16 mL) was stirred with heating at 80° C. for 15 hrs. The mixture was allowed to cool to room temperature and the precipitated solid was collected by filtration and washed with ethanol to give the title compound as a white powder (397 mg, 73%). melting point: 227-229° C.
  • 6
  • [ 67515-74-6 ]
  • [ 369360-49-6 ]
  • [ 248929-73-9 ]
YieldReaction ConditionsOperation in experiment
121 (2RS,3R)-3-Amino-4-cyclohexyl-N-(4-fluoro-3-(trifluoromethyl)benzyl)-2-hydroxybutanamide Hydrochloride Example 121 (2RS,3R)-3-Amino-4-cyclohexyl-N-(4-fluoro-3-(trifluoromethyl)benzyl)-2-hydroxybutanamide Hydrochloride The product of example 23A and 3-(trifluoromethyl)-4-fluorobenzylamine were processed as in example 101 to provide the title compound. MS (APCI) m/e 377 (M+H)+ 1H NMR (300 MHz, MeOH-d4) δ 7.64 (m, 2H), 7.29 (t, 1H), 4.45 (q, 2H), 4.12 (d, 1H), 3.49 (m, 1H), 0.80-1.80 (me, 13H).
  • 7
  • [ 75-44-5 ]
  • [ 54410-17-2 ]
  • CH2Cl2:CH3OH [ No CAS ]
  • [ 67515-74-6 ]
  • [ 581811-69-0 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In toluene 209 N-[4-fluoro-3-(trifluoromethyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea EXAMPLE 209 N-[4-fluoro-3-(trifluoromethyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea 4-Fluoro-3-(trifluoromethyl)benzylamine (0.8 g, 4.15 mmol) in toluene (20 mL) was refluxed with 20% w/v phosgene solution in toluene (2.1 mL) overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was again taken up in toluene (25 mL) and was stirred overnight at 80° C. with DIEA (2 mL, 11.5 mmol) and 5-amino-3-methylisoquinoline (500 mg, 3.16 mmol). The mixture was cooled to room temperature, concentrated in vacuo, and the residue was purified by silica gel chromatography (97:3 CH2Cl2:CH3OH, eluant) to provide the title compound. The corresponding hydrochloride salt was prepared by treatment with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 9.18 (s, 1H), 8.72 (s, 1H), 8.16 (d, 1H, J=7.8 Hz), 7.70-7.77 (m, 4H), 7.48-7.54 (m, 3H), 7.14 (t, 1H, J=5.9 Hz), 4.42 (d, 2H, J=6.1 Hz), 2.64 (s, 3H); MS (ESI+) m/z 378 (M+H).
With N-ethyl-N,N-diisopropylamine In toluene 209 N-[4-fluoro-3-(trifluoromethyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea EXAMPLE 209 N-[4-fluoro-3-(trifluoromethyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea 4-Fluoro-3-(trifluoromethyl)benzylamine (0.8 g, 4.15 mmol) in toluene (20 mL) was refluxed with 20% w/v phosgene solution in toluene (2.1 mL) overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was again taken up in toluene (25 mL) and was stirred overnight at 80° C. with DIEA (2 mL, 11.5 mmol) and 5-amino-3-methylisoquinoline (500 mg, 3.16 mmol). The mixture was cooled to room temperature, concentrated in vacuo, and the residue was purified by silica gel chromatography (97:3 CH2Cl2:CH3OH, eluant) to provide the title compound. The corresponding hydrochloride salt was prepared by treatment with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 9.18 (s, 1H), 8.72 (s, 1H), 8.16 (d, 1H, J=7.8 Hz), 7.70-7.77 (m, 4H), 7.48-7.54 (m, 3H), 7.14 (t, 1H, J=5.9 Hz), 4.42 (d, 2H, J=6.1 Hz), 2.64 (s, 3H); MS (ESI+) m/z 378 (M+H).
  • 8
  • 3-methyl-2-oxo-4-imidazolidinecarboxylic acid [ No CAS ]
  • [ 67515-74-6 ]
  • N-[4-fluoro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4-imidazolidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% Stage #1: 3-methyl-2-oxo-4-imidazolidinecarboxylic acid With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Stage #2: 4-fluoro-3-trifluoromethylbenzylamine In dichloromethane 84 Example 84 N-[4-Fluoro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4- imidazolidinecarboxamide (E84) (in a form obtainable or prepared from (4S)-2-oxo- S-^phenylmethyOoxyJcarbonyl^-imidazolidinecarboxylic acid); A mixture of 3-methyl-2-oxo-4-imidazolidinecarboxylic acid (86 mg, 0.6 mmol) (prepared as described in Example 28 from 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate, itself prepared as described in step (iii) of Example 13, starting originally from (4S)-2-oxo-3-[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid), N-ethyl morpholine (0.380 ml, 3.00 mmol), 1- hydroxybenzotriazole hydrate (110 mg, 0.720 mmol) and 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (138 mg, 0.720 mmol) in dichloromethane (9 ml) was stirred at room temperature for 10 minutes, under an argon atmosphere. [4-Fluoro-3-(trifluoromethyl)phenyl]methyl}amine (127 mg, 0.660 mmol) was added and the reaction was stirred overnight under an argon atmosphere. The reaction mixture was diluted with dichloromethane (10ml) and the solution was washed with saturated sodium hydrogen carbonate solution (10ml), water (10ml) and brine (10ml). The organic solution was dried and the solvent was evaporated in vacuo. The residue was purified by mass-directed automated HPLC. Fractions containing product were collected and the solvent was evaporated in vacuo to give N-[4-fluoro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4- imidazolidinecarboxamide (8 mg, 4% yield) as a white solid. LC/MS [M+H]+ = 320, retention time = 1.87 minutes.
  • 9
  • methyl rac-6-(2-(((2S*,5R*)-5-hydroxymethyl-1,4-dioxan-2-yl)methyl)-2H-tetrazol-5-yl)-2-methylpyrimidine-4-carboxylate [ No CAS ]
  • [ 67515-74-6 ]
  • rac-N-(4-fluoro-3-trifluoromethyl-benzyl)-6-[2-((2S*,5R*)-5-hydroxymethyl-[1,4]dioxan-2-ylmethyl)-2H-tetrazol-5-yl]-2-methyl-pyrimidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% In N,N-dimethyl acetamide at 85℃; for 18h; 70 Example 70 rac-W-(4-Fluoro-3-(trifluoromethyl)benzyl)-6-(2-(((2S*,5/?*)-5-(hydroxymethyl)-1,4-dioxan-2- yl)methyl)-2H-tetrazol-5-yl)-2-methylpyrimidine-4-carboxamideA mixture of rac-methyl 6-(2-(((2S5R*)-5-(hydroxymethyl)-1 ,4-dιoxan-2-yl)methyl)-2H- tetrazol-5-yl)-2-methylpyrιmιdιne-4-carboxylate (prepared as described in step 1 of the synthesis of rac-λ/-(4-fluoro-3-methylbenzyl)-6-(2-(((2S*,5R*)-5-(hydroxymethyl)-1 ,4-dιoxan-2-yl)methyl)-2H- tetrazol-5-yl)-2-methylpyϖmιdιne-4-carboxamιde, Example 67) (100 mg, 0 285 mmol), 4-fluoro-3- tϖfluoromethylbenzylamine (165 mg, 0 856 mmol), and dimethylacetamide (1 mL) was heated to 85 0C for 18 hours The title compound was isolated as a solid by reverse phase preparative HPLC (52 mg, 36%) MS (ES+) m/z 512 (M+H) 1H NMR (400 MHz, DMSO-Cf6) δ ppm 2 84 (s, 3 H), 3 31 - 3 52 (m, 5 H), 3 78 (dd, J= 11 4, 1 8 Hz, 1 H), 3 99 (dd, J= 11 4, 2 2 Hz, 1 H), 4 03 - 4 14 (m, 1 H), 4 59 (d, J=6 2 Hz, 2 H), 4 65 (t, J=5 7 Hz, 1 H), 4 81 - 5 00 (m, 2 H), 7 41 - 7 53 (m, 1 H), 7 69 - 7 83 (m, 2 H), 8 41 (s, 1 H), 9 66 (t, J=6 04 Hz, 1 H)
  • 12
  • [ 1217315-21-3 ]
  • [ 67515-74-6 ]
  • [ 1217482-74-0 ]
  • [ 1217315-22-4 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 16h;
  • 13
  • 4-(4-chlorophenyl)thiazole-2-carboxylic acid [ No CAS ]
  • [ 67515-74-6 ]
  • 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid 4-fluoro-3-trifluoromethyl-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 4-(4-chlorophenyl)thiazole-2-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: 4-fluoro-3-trifluoromethylbenzylamine In tetrahydrofuran at 20℃; for 24h; 2.53 Compound 53. 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid 4-fluoro-3-trifluoromethyl-benzylamide (B250303) 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid (51 mg, 0.18 mmol) was dissolved in THF (5 mL), followed by addition of CDI (37 mg, 0.23 mmol). The slurry mixture was stirred at RT for 1 hour. 4-Fluoro3-(trifluoromethyl)benzylamine (45 mg, 0.23 mmol) dissolved in THF (2 mL) was added to it. The reaction was continued at RT for 24 hours. After removal of the solvent, the residue was dissolved in dichloromethane. After filtration through a pad of silica eluted with chloroform, the concentrated residue was applied on chromatotron (silica) eluted with chloroform to afford a component (Rf=0.25, chloroform, silica). It was an off-white semisolid (47 mg, Y=80%). The structure of the compound was confirmed by NMR
  • 14
  • [ 67515-74-6 ]
  • [ 1849-02-1 ]
  • [ 1258460-63-7 ]
YieldReaction ConditionsOperation in experiment
at 130℃; Step B: (4-Fluoro-3-trifluoromethyl-benzyl)-(1-methyl-1H-benzimidazol-2-yl)-amineA mixture of <strong>[1849-02-1]2-chloro-1-methyl-1H-benzimidazole</strong> (915 mg, 5.5 mmol) and 4-fluoro-3-trifluoromethyl-benzylamine (4.24 g, 22.0 mmol) was stirred at 130 C. overnight. The resulting mixture was diluted with EtOAc, washed with H2O, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by recrystallization from hexane to yield (4-fluoro-3-trifluoromethyl-benzyl)-(1-methyl-1H-benzimidazol-2-yl)-amine MS 324 (M+1)+
  • 16
  • [ 67515-74-6 ]
  • [ 1392000-76-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 96 h / 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / -15 - 20 °C / Inert atmosphere 3: triethylamine / methanol / 48 h / 45 °C
  • 17
  • [ 67515-74-6 ]
  • [ 1392000-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 96 h / 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / -15 - 20 °C / Inert atmosphere
  • 18
  • [ 67515-74-6 ]
  • [ 1864-94-4 ]
  • [ 1392000-93-9 ]
  • 19
  • [ 1616340-76-1 ]
  • [ 67515-74-6 ]
  • [ 1616342-26-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; for 1h; 25.1 Example 25 Preparation of Compound 25 (2S,5R,13aS)-N-(4-fluoro-3-(1rifluorom.ethyl)benz.yl)-8-hydroxy-7,9-dioxo- 2,3,4,5,7,9,13, 13a-octahydro-2,5-rnethanopyrido[ ,2':4,5]pyrazino[2, 1 - b] [ 1 ,3]oxazepine- 10-carboxamide Steps 1 and 2 Preparation of Compound 25 (2S,5R,13aS)-N-(4-fluoro-3-(1rifluorom.ethyl)benz.yl)-8-hydroxy-7,9-dioxo- 2,3,4,5,7,9,13, 13a-octahydro-2,5-rnethanopyrido[ ,2':4,5]pyrazino[2, 1 - b] [ 1 ,3]oxazepine- 10-carboxamide Steps 1 and 2 15-B (43 mg, 0.13 mmol) was treated with acetonitrile ( 1 mL), (4-fluoro- 3-(trifluoromethyi)phenyi)metiiaiiamine (29 mg, 0.15 mmol), HATU (62 mg, 0.16 mmol), and N,N-diisopropyIethylamine (26 mg, 0.20 mmol). The reaction mixture was stirred at room temperature for one hour and magnesium bromide (62 mg, 0.34 mmol) was added. The mixture was sealed and heated to 50 °C. After 60 minutes, the reaction mixture was quenched with 0.2M HCl(aq), di luted with brine, and thrice extracted into DCM. HPLC purification (Acetonitrile: water, 0.1% TFA) afforded Compoimd 25. 1H~ NMR (400 MHz, Chloroform-d) δ 10.44 (s, 1 H), 8.29 (s, 1H), 7.56 - 7.38 (m, 2H), 7.06 (t, J = 9.2 Hz, 1H), 5.30 (dd, J - 9.3, 3.5 Hz, I I I . 5.21 (s, 1 H), 4.65 - 4.45 (m, 3H), 4.21 (dd, J = 12.8, 3.4 Hz, 1H), 3.95 (dd, J = 12.4, 9.7 Hz, 1H), 2.1 1 - 1.89 (m, 4H), 1.89 - 1.74 (m, 1 H), 1 .53 (dt, J = 12.4, 3.2 Hz, 1H). LCMS-ESI+ (m/z): U calculated for C22H19F4N3O5: 482.14; found: 482.2.
  • 20
  • [ 1624255-71-5 ]
  • [ 67515-74-6 ]
  • [ 1624256-13-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane at 20℃; for 16h;
  • 21
  • [ 67515-74-6 ]
  • C23H15ClF7NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: caesium carbonate / acetonitrile / 0.17 h / 160 °C / Microwave irradiation
  • 22
  • [ 67515-74-6 ]
  • [ 1254208-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: caesium carbonate / acetonitrile / 0.17 h / 160 °C / Microwave irradiation
  • 23
  • [ 67515-74-6 ]
  • [ 1254205-80-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: caesium carbonate / acetonitrile / 0.17 h / 160 °C / Microwave irradiation 3: water; sodium hydroxide / tetrahydrofuran / 50 °C
  • 24
  • [ 67515-74-6 ]
  • [ 1254205-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: caesium carbonate / acetonitrile / 0.17 h / 160 °C / Microwave irradiation 3: water; sodium hydroxide / tetrahydrofuran / 50 °C
  • 25
  • [ 67515-74-6 ]
  • [ 69812-51-7 ]
  • C16H13F4NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃;
  • 26
  • 1-(3-amino-1H-1,2,4-triazol-5-yl)piperidine-4-carboxylic acid [ No CAS ]
  • [ 67515-74-6 ]
  • 1-(3-amino-1H-1,2,4-triazol-5-yl)-N-(4-fluoro-3-(trifluoromethyl)benzyl)piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With hydrogenchloride In ethyl acetate at 20℃; 54 Step 3: 2-(4-bromophenoxy)-1-(piperazin-1-yl)butan-1-one General procedure: Step 3: 2-(4-bromophenoxy)-1-(piperazin-1-yl)butan-1-onetert-Butyl 4-(2-(4-bromophenoxy)butanoyl)piperazine-1-carboxylatewasdissolved in ethyl acetate and treated with hydrogen chloride(4M solution in ethyl acetate). The reaction mixturewas stirred at ambient temperature and followed by TLC20 (chloroform/methanol 9:1). When substrate was no longerdetected, the precipitate was filtered off and washedwith ether to give the title compoundas the hydrochloride salt (white solid). The hydrochloride salt was dissolvedin 1M NaOH, and the free amine was extractedinto dichloromethane, washed with brine, and dried over anhydrous MgS04. The solvent was removed under reduced pressureto give the title compoundas a colorless oil (91% yield)
  • 27
  • [ 1112182-62-3 ]
  • [ 67515-74-6 ]
  • [ 1112174-59-0 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 4-(2-(((trans)-4-(hydroxymethyl)cyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methylpicolinic acid With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.25h; Stage #2: 4-fluoro-3-trifluoromethylbenzylamine With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 18h;
  • 28
  • [ 869297-03-0 ]
  • [ 67515-74-6 ]
  • 4-[({2-[([4-fluoro-3-(trifluoromethyl)phenyl]methyl}amino)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl}methyl)oxy]methyl}benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 15 h / 80 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 1 h / Heating
  • 29
  • [ 124612-15-3 ]
  • [ 67515-74-6 ]
  • 3-((4-fluoro-3-(trifluoromethyl)benzyl)amino)-5-(trifluoromethyl)cyclohex-2-enone [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In ethanol; ethyl acetate for 5h; Reflux; 1.1 4.1.1.1 .3-((4-fluoro-3-(trifluoromethyl) benzyl) amino)-5-(trifluoromethyl) cyclohex-2-enone (4f) To a stirred solution of 5-(trifluoromethyl) -1,3- cyclohexane dione (1 mmol 180 mg) in a mixture of absolute Ethanol (33 ml) and Ethyl acetate (35 ml), 4-fluoro-3-(trifluoromethyl) benzylamine (1 mmol, 147 mg) was added and the reaction mixture was refluxed and stirred for 5 h. The progress of the reaction was monitored by TLC. During that time, one-half of the solvents were slowly removed, via a Dean Stark trap, and after cooling, replaced with an equal amount of anhydrous diethyl ether. After completion of the reaction as indicated by TLC, the remaining solvent was removed through vacuum and the product was recrystallized with hexane and ethyl acetate to give the title compound. Yellow powder product formed. Yield: 52%(183 mg); mp: 150-152 °C; TLC: Rf = 0.84 (S1); EIMS m/z: 177(42%), 355 (100%) (M+), 356 (16.6%) (M+1); 1HNMR (400Mz, δ ppm, DMSO-d6) δ 2.04(d, 2H), 2.56(t, 1H), 2.99-3.01-(d, 2H), 4.03(d, 2H), 4.34(s, 1H), 5.01(s, 1H), 7.67(d, 1H), 7.89(d, 2H). 13CNMR (400Mz, δ ppm, DMSO-d6) 22.71, 28.72, 36.77, 36.52, 39.00, 47.83, 100.25, 113.99, 115.69, 118.63, 121.32, 126.93, 131.91, 137.61, 138.75, 155.70, 163.20, 197.
  • 30
  • [ 67515-74-6 ]
  • [ 79-04-9 ]
  • C10H8ClF4NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 25℃; for 1h; Inert atmosphere; 3 Preparation of compound C, the reaction process is as follows: At 0 ° C,To a nitrogen-protected dry single-mouth bottle was added ultra dry solvent DCM (5 mL), compound Cc (193 mg, 1 mmol), chloroacetyl chloride (135.6 mg, 1.2 mmol) and triethylamine (151.5 mg, 1.5 mmol), then The reaction was carried out for 1 h at 25 ° C (TLC tracking); the obtained system was successively subjected to DCM (15 mL) extraction, water (10 mL) and saturated hydrogen carbonate.The sodium solution (10 mL) was washed, and brine (10 mL) was washed. The organic phase was collected, and the organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure and dried to give a crude amide intermediate product directly for subsequent reaction;
  • 31
  • [ 67515-74-6 ]
  • C19H25F4N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 0 - 25 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / 6 h / 60 °C
  • 32
  • [ 67515-74-6 ]
  • N<SUP>3</SUP>-cyclopropyl-N<SUP>3</SUP>-(4-fluoro-3-(trifluoromethyl)benzyl)-N<SUP>1</SUP>,N<SUP>1</SUP>-dimethyl-1H-1,2,4-triazole-1,3-disulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 12 h / 25 °C 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 25 °C
  • 33
  • [ 171967-86-5 ]
  • [ 67515-74-6 ]
  • N<SUP>3</SUP>-(4-fluoro-3-(trifluoromethyl)benzyl)-N<SUP>1</SUP>,N<SUP>1</SUP>-dimethyl-1H-1,2,4-triazole-1,3-disulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With pyridine In tetrahydrofuran at 25℃; for 12h;
  • 34
  • [ 32833-96-8 ]
  • [ 1188429-06-2 ]
  • [ 67515-74-6 ]
  • [ 1188425-55-9 ]
YieldReaction ConditionsOperation in experiment
6 mg General procedure: To a mixture of 37 (30 mg, 0.076 mmol) and (3,4-difluorophenyl)methanamine (109 mg, 0.765 mmol) in ethanol (2 mL) was added TEA (0.107 mL, 0.765 mmol) and the mixture heated at 90 oC for 18 h. At this point LC-MS indicated completion of the reaction and the appearance of the desired product. The reaction mixture was cooled and the residue purified by HPLC to afford the desired product as a thick film. (2.5 mg, 6%).
  • 35
  • [ 67515-74-6 ]
  • 2-(4-hydroxyazepan-1-yl)-N,N-dimethyl-2-phenylacetamide [ No CAS ]
  • 2-(4-[4-fluoro-3-(trifluoromethyl)benzyl]amino}azepan-1-yl)-N,N-dimethyl-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-(4-hydroxyazepan-1-yl)-N,N-dimethyl-2-phenylacetamide With methanesulfonyl chloride; triethylamine In dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere; Stage #2: 4-fluoro-3-trifluoromethylbenzylamine In dimethyl sulfoxide at 20℃; for 15h; Inert atmosphere;
  • 36
  • 3,4-dihydronaphthalen-1-yl-sulfofluoridate [ No CAS ]
  • [ 67515-74-6 ]
  • C18H15F4NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With 1,4-diaza-bicyclo[2.2.2]octane; calcium(II) bis(trifluoromethanesulfonyl)imide In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
  • 37
  • [ 50593-73-2 ]
  • [ 67515-74-6 ]
  • N-[4-fluoro-3-(trifluoromethyl)benzyl]-6-methoxy-2-methylquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 110℃; Inert atmosphere;
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