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[ CAS No. 330-17-6 ] {[proInfo.proName]}

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Chemical Structure| 330-17-6
Chemical Structure| 330-17-6
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Product Details of [ 330-17-6 ]

CAS No. :330-17-6 MDL No. :MFCD00040906
Formula : C8H5F3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :UMOGQQWVQUQTQA-UHFFFAOYSA-N
M.W : 222.18 Pubchem ID :2777858
Synonyms :

Calculated chemistry of [ 330-17-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.31
TPSA : 62.6 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) : -4.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 3.95
Log Po/w (WLOGP) : 4.26
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 2.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.0332 mg/ml ; 0.00015 mol/l
Class : Soluble
Log S (Ali) : -4.96
Solubility : 0.00241 mg/ml ; 0.0000108 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.372 mg/ml ; 0.00167 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.42

Safety of [ 330-17-6 ]

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

Application In Synthesis of [ 330-17-6 ]

* 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 [ 330-17-6 ]

[ 330-17-6 ] Synthesis Path-Downstream   1~75

  • 1
  • [ 332-26-3 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 140℃;
  • 2
  • [ 352-68-1 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
(i) Br2, (irradiation), CCl4, (ii) aq. HNO3; Multistep reaction;
  • 3
  • [ 330-17-6 ]
  • [ 74483-45-7 ]
YieldReaction ConditionsOperation in experiment
(i) LiAlH4, (ii) SOCl2; Multistep reaction;
  • 4
  • [ 330-17-6 ]
  • [ 79865-54-6 ]
YieldReaction ConditionsOperation in experiment
70% With dihydrogen peroxide; dicyclohexyl-carbodiimide In diethyl ether; dichloromethane at 0 - 2℃;
  • 6
  • [ 330-17-6 ]
  • [ 17128-26-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid
YieldReaction ConditionsOperation in experiment
4-Fluormercaptocarbonyl-benzoesaeure, SF4, Autoklav, 150grad-175grad;
p-Trichlormethylmercaptobenzoesaeurechlorid, 1) SbF3, Δ, 2) W., Acn., Δ;
  • 8
  • [ 6302-65-4 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / liquid ammonia / 0.5 h / Irradiation; PRK-4 mercury lamp 2: 94 percent / HCl / acetic acid / 6 h / 110 °C
  • 9
  • [ 330-17-6 ]
  • [ 384-37-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH 3: SO3/H2SO4, NaN3 4: (i) H2SO4, NaNO2, (ii) aq. Na2S2O4, H2SO4
  • 10
  • [ 330-17-6 ]
  • [ 1948-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH
  • 11
  • [ 330-17-6 ]
  • [ 17095-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH 3: SO3/H2SO4, NaN3
  • 12
  • [ 330-17-6 ]
  • [ 17095-18-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH 3: SO3/H2SO4, NaN3 4: (i) H2SO4, NaNO2, (ii) aq. Na2S2O4, H2SO4 5: aq. HCl, SnCl2
  • 13
  • [ 330-17-6 ]
  • [ 17128-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH 3: SO3/H2SO4, NaN3 4: (i) H2SO4, NaNO2, (ii) aq. Na2S2O4, H2SO4 5: aq. HCl, SnCl2 6: (i) NaNO2, H2SO4, AcOH, (ii) /BRN= 507140/
  • 14
  • [ 330-17-6 ]
  • [ 3771-34-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH 3: SO3/H2SO4, NaN3 4: (i) H2SO4, NaNO2, (ii) aq. Na2S2O4, H2SO4 5: aq. HCl, SnCl2 6: (i) aq. HCl, NaNO2, (ii) /BRN= 507140/
  • 15
  • [ 330-17-6 ]
  • [ 17128-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. HNO3, H2SO4 2: CrO3, AcOH 3: SO3/H2SO4, NaN3 4: (i) AcOH, H2SO4, NaNO2, (ii) /BRN= 507140/
  • 16
  • [ 696-61-7 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran 2: (i) Br2, (irradiation), CCl4, (ii) aq. HNO3
  • 17
  • [ 330-17-6 ]
  • [ 29805-57-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) LiAlH4, (ii) SOCl2 2: (i) NaH, DMSO, (ii) /BRN= 2364099/
  • 18
  • [ 330-17-6 ]
  • 2-(2-Dimethylamino-ethyl)-2-(4-trifluoromethylsulfanyl-benzyl)-malonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) LiAlH4, (ii) SOCl2 2: (i) NaH, DMSO, (ii) /BRN= 2364099/ 3: (i) NaH, DMSO, (ii) /BRN= 605280/
  • 19
  • [ 330-17-6 ]
  • [ 312-22-1 ]
YieldReaction ConditionsOperation in experiment
87% With potassium permanganate; acetic acid In water at 20℃; for 16h; 17 Example 17 (S)-N-(1-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-cyanopropan-2-yl)-4-(trifluoromethylsulfonyl)benzamide Example 17 (S')-N-('l-('7-chloro-l-hvdroxy-l,3-dihvdrobenzo[cl[l.,21oxaborol-6-yloxy')-2-cvanopropan -2-vl)-4-ftrifluoromethvlsulfonvl)benzamide To the solution of 4-(trifluoromethylthio)benzoic acid (5g, 22.5 mmol) is dissolved in water (50 mL) and acetic acid (150 mL) is added potassium permanganate (20g, 126.5 mmol) at rt. The reaction is stirred for 16 h, diluted with ethyl acetate and washed with water. The organic layer is dried over MgS04 and concentrated to give 4-(trifluoromethylsulfonyl)benzoic acid (5g, 87% yield).
86% With oxone In methanol; water at 20 - 50℃; for 102h; 83.A To a solution of 4-trifluoromethylsulfanyl-benzoic acid (250 mg, 1.13 mmol) in methanol (10 mL) and water (8 mL) is added oxone (5.59 g, 6.75 mmol) and the reaction is stirred first at 50 °C for 6 hours, then at room temperature for 4 days. The mixture is diluted with ethyl acetate and water and the layers are separated. The aqueous layer is extracted with ethyl acetate and the combined organic phase washed with brine, dried over Na2SO4, filtered, and the solvent is removed in vacuo to afford the desired product (245 mg, 86%). LCMS: 253.00 (M-H+).
With potassium permanganate; acetic acid In water at 20℃; for 16h; 19 Example 19 N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(trifluoromethylsulfonyl)benzamide 4-(trifluoromethylthio)benzoic acid (200 mg, 0.9 mmol) was dissolved in water (2 mL) and acetic acid (4 mL) and treated with potassium permanganate (711 mg, 4.5 mmol) at room temperature. The reaction was allowed to stir for 16 h, diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO/i) and concentrated to yield 4-(trifluoromethylsulfone)benzoic acid.
With potassium permanganate; acetic acid In water at 20℃; for 16h; 19 4-(trifluoromethylthio)benzoic acid (200 mg, 0.9 mmol) was dissolved in water (2 mL) and acetic acid (4 mL) and treated with potassium permanganate (711 mg, 4.5 mmol) at room temperature. The reaction was allowed to stir for 16 h, diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4) and concentrated to yield 4-(trifluoromethylsulfone)benzoic acid.
500 mg With potassium permanganate; acetic acid In water at 20℃; for 12h; 76 Synthesis of II-A-24b A mixture of KMnCL (2000 mg, 12.66 mmol) and 4- (trifluoromethylsulfanyl)benzoic acid (500 mg, 2.25 mmol) in acetic acid (15 mL) and water (5 mL) was stirred at 20 °C for 12 hours. The mixture was diluted with water (20 mL) and the aqueous layer was extracted with EtOAc (20 mL x 2). The combined organic phase was washed with water (20 mL x 2) and brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated to give the product (500 mg, 1.97 mmol) as a solid. NMR (400MHz, CD3OD) dH = 8.37 (d, 2H), 8.20 (d, 2H).

  • 20
  • [ 330-17-6 ]
  • [ 128273-56-3 ]
  • [ 56602-33-6 ]
  • [ 329317-33-1 ]
YieldReaction ConditionsOperation in experiment
With dmap In N,N-dimethyl-formamide 5 Example 5 Example 5 N-(4-Trifluoromethylsulfonylbenzyl)-4-trifluoromethylsulfonylbenzamide (5). A mixture of 4-(trifluoromethylthio)benzoic acid (300 mg, 1.35 mmol), 4-(trifluoromethylthio)benzylamine (308 mg, 1.49 mmol), benzotriazol-1-yl-oxytris-(dimethylamino)-phosphonium hexafluorophosphate (1.8 g, 4.05 mmol) and DMAP (198 mg, 1.62 mmol) in DMF (15 mL) was stirred at rt overnight. The reaction was diluted with ether, washed with water, dried and concentrated to give 520 mg (94%) of N-(4-trifluoromethylthiobenzyl)-4-trifluoromethylthiobenzamide as a white solid. 1H-NMR (360 MHz, DMSO-d6) δ 9.27 (m, 1H, NH), 8.01 (d, J=8.0 Hz, 2H), 7.82 (d, J=8.0 Hz, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 4.54 (d, J=5.8 Hz, 2H, NCH2). MS-EI m/z 411 [M+]. N-(4-trifloromethylthiolbenzyl)-4-trifloromethylthiobenzamide (300 mg, 0.73 mmol) was oxidized using 3-chloroperbenzoic acid (879 mg, excess) to give 310 mg (90%) of N-(4-trifluoromethylsulfonylbenzyl)-4-trifluoromethylsulfonylbenzamide. 1H-NMR (360 MHz, DMSO-d6) δ 9.61 (m, 1H, NH), 8.28 (s, 4H), 8.10 (d, J=8.5 Hz, 2H), 7.79 (d, J=8.5 Hz, 2H), 4.69 (d, J=6.1 Hz, 2H, NCH2).
  • 21
  • [ 330-17-6 ]
  • [ 3468-17-5 ]
  • [ 1178608-83-7 ]
YieldReaction ConditionsOperation in experiment
With PS-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20.0℃; for 60.0h; A suspension of 4-(trifluoromethylthio)benzoic acid (0.333 g, 1.499 mmol; Aldrich) and 1 H-indole-6-methanamine (0.146 g, 0.999 mmol; Chemgenix) in 10: 1 dichloromethane- MN-dimethylformamide (16.5 mL) was treated with PS-carbodiimide (1.5 g, 1.875 mmol; Biotage) and stirred at room temperature for 60 hours. The suspension was filtered through diatomaceous earth, rinsing with dichloromethane. The resulting material was purified by flash chromatography (40 g silica gel column, 5-95% gradient of ethyl acetate in hexanes), then purified further by preparative HPLC [Waters 30x100 mm XBridge Cl 8 OBD 5 mu column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, CDCl3) delta ppm 4.74 (d, J=5.4 Hz, 2 H), 6.40 (s, 1 H), 6.55 (ddd, J=3.1, 2.0, 1.0 Hz, 1 H), 7.10 (dd, J=8.1 , 1.7 Hz, 1 H), 7.20 - 7.25 (m, 1 H), 7.41 (s, 1 <n="59"/>H), 7.63 (d, J=8.1 Hz, 1 H), 7.66 - 7.73 (m, 2 H), 7.81 (dt, J=8.5, 2.0 Hz, 2 H), 8.13 - 8.29 (m,1 H); MS (+DCI) m/z 351 (M+H)+, 368 (M+NH4)+.
  • 22
  • [ 864264-03-9 ]
  • [ 330-17-6 ]
  • [ 1178607-02-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU In ISOPROPYLAMIDE at 20℃; 12 In a 96 deep well plate, 4-(trifluoromethylthio)benzoic acid (23 mg, 0.10 mmol) was added dissolved in dimethylacetamide (0.4 mL), followed by O-(7-azabenzotriazol-l-yl)- N,N5N'5N'-tetramethyluronium hexafluorophosphate (HATU, 48 mg, 0.12 mmol, 1.2 equivalents) dissolved in dimethylacetamide (0.3 mL), triethylamine (26 mg, 0.25 mmol, 2.4 equivalents) dissolved in dimethylacetamide (0.3 mL), and finally the N-(I -methyl- lH-indol- 6-yl)methanamine (0.7 mL of a 0.2 M solution in dimethylacetamide, 1.4 equivalents). This was shaken at room temperature overnight. The reaction solution was concentrated to dryness in vacuo, dissolved in 1 : 1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC (Phenomenex Luna C8(2) 5 urn IOOA AXI A column (30mm x 75mm), a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 40mL/min (0-0.5 min 10% A, 0.5-6.0 min linear gradient 10-100% A, 6.0-7.0 min 100% A, 7.0-8.0 min linear gradient 100-10% A)) to give the titled product: 1H NMR (500 MHz, OMSO-Ci(SD2O) δ ppm 3.76 (s, 3 H) 4.61 (s, 2 H) 6.40 (dd, J=3.1, 0.6 Hz, 1 H) 7.05 (dd, J=8.1, 1.4 Hz5 1 H) 7.28 (d, J=3.1 Hz, 1 H) 7.39 (s, 1 H) 7.51 (d, J=7.9 Hz, 1 H) 7.81 - 7.85 (m, 2 H) 7.97 - 8.01 (m, 2 H), 9.22 (s, 1 H); MS (ESI+) m/z 365.0 (M+H)+.
  • 23
  • [ 330-17-6 ]
  • 4-(dimethylamino)benzylamine dihydrochloride salt [ No CAS ]
  • [ 1190069-78-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; B; 17 N-[4-(dimethylamino)benzyl]-4-[(trifluoromethyl)thio]benzamide A suspension of an amine (0.5 mmol) and a benzoic acid (0.5 mmol) in anhydrous N,N-dimethylformamide (2 mL) was treated with N,N-diisopropylethylamine (iPr2NEt; 245 μL. 1.5 mmol, 3.0 equivalents: Acros) and O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoro-phosphate (HATU; 285 mg, 0.75 mmol, 1.5 equivalents; Aldrich). The mixture was stirred overnight at room temperature, and diluted with dichloromethane (20 mL). The solution was washed with dilute aqueous ammonium chloride (2×7 mL). dilute aqueous sodium bicarbonate (2×7 mL). and brine (2×7 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by either flash chromatography [Analogix pre-packed silica gel cartridges, 5-50% gradient of ethyl acetate/hexanes], or by preparative HPLC [Waters Xterra RP18 30×100 mm column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with sodium hydroxide)] to afford the desired amide product as its free base. Alternatively, the compound was purified on a Waters Symmetry C8 30×100 mm column (flow rate 40 mL/minute, 5-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid) to afford the amide product after evaporation of solvent. The product was prepared from 4-trifluoromethylthiobenzoic acid (133 mg) and 4-(dimethylamino)benzylamine dihydrochloride (134 mg) according to Method B: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.85 (s, 6H), 4.36 (d, J=5.8 Hz, 2H), 6.57-6.75 (m, J=8.8 Hz, 2H), 7.08-7.23 (m, J=8.8 Hz, 2H), 7.76-7.86 (m, J=8.5 Hz, 2H), 7.92-8.06 (m, J=8.5 Hz, 2H), 9.08 (t, J=5.8 Hz, 1H); MS (DCI/NH3) m/z 355.1 (M+H)+; Anal. C17H17F3N2OS: C, H, N.
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; 17 A suspension of an amine (0.5 mmol) and a benzoic acid (0.5 mmol) in anhydrous N,N-dimethylformamide (2 mL) was treated with N,N-diisopropylethylamine (iPr2NEt; 245 µL, 1.5 mmol, 3.0 equivalents; Acros) and O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoro-phosphate (HATU; 285 mg, 0.75 mmol, 1.5 equivalents; Aldrich). The mixture was stirred overnight at room temperature, and diluted with dichloromethane (20 mL). The solution was washed with dilute aqueous ammonium chloride (2 x 7 mL), dilute aqueous sodium bicarbonate (2 x 7 mL), and brine (2 x 7 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by either flash chromatography [Analogix pre-packed silica gel cartridges, 5-50% gradient of ethyl acetate/hexanes], or by preparative HPLC [Waters Xterra RP18 30×100 mm column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with sodium hydroxide)] to afford the desired amide product as its free base. Alternatively, the compound was purified on a Waters Symmetry C8 30×100 mm column (flow rate 40 mL/minute, 5-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid) to afford the amide product after evaporation of solvent. The product was prepared from 4-trifluoromethylthiobenzoic acid (133 mg) and 4-(dimethylamino)benzylamine dihydrochloride (134 mg) according to Method B: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.85 (s, 6 H), 4.36 (d, J=5.8 Hz, 2 H), 6.57 - 6.75 (m, J=8.8 Hz, 2 H), 7.08 - 7.23 (m, J=8.8 Hz, 2 H), 7.76 - 7.86 (m, J=8.5 Hz, 2 H), 7.92 - 8.06 (m, J=8.5 Hz, 2 H), 9.08 (t, J=5.8 Hz, 1 H); MS (DCI/NH3) m/z 355.1 (M+H)+; Anal. C17H17F3N2OS: C, H, N.
  • 24
  • [ 368869-95-8 ]
  • [ 330-17-6 ]
  • [ 1190069-52-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU In ISOPROPYLAMIDE at 20℃; A; 1 N-[3-(1H-pyrrol-1-yl)benzyl]-4-[(trifluoromethyl)thio]benzamide In a 96 deep well plate, 4-(trifluoromethylthio)benzoic acid (23 mg, 0.10 mmol) was added dissolved in N,N-dimethylacetamide (0.4 mL), followed by O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) (48 mg. 0.12 mmol, 1.2 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), triethylamine (26 mg, 0.25 mmol, 2.4 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), and finally the amine (0.7 mL of a 0.2 M solution in N,N-dimethylacetamide, 1.4 equivalents). This was shaken at room temperature overnight. The reaction solution was concentrated to dryness in vacuo, dissolved in 1:1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC on a Phenomenex Lunar Combi-HTS C8(2) 5 μm 100 (2.1 mm×30 mm) using a gradient of 10-100% acetonitrile (A) and 0.1% trifluoroacetic acid (B) in water at a flow rate of 2.0 mL/minute (0-0.1 minutes 10% A, 0.1-2.6 minutes 10-100% A, 2.6-2.9 minutes 100% A, 2.9-3.0 minutes 100-10% A.) to give the product. The product was prepared from (3-(1H-pyrrol-1-yl)phenyl)methanamine according to Method A: 1H NMR (500 MHz, DMSO-d6) δ ppm 4.54-4.58 (m, 2H), 6.28 (t, J=2.1 Hz, 2H), 7.22 (d, J=6.4 Hz, 1H), 7.32 (t, J=2.1 Hz, 2H), 7.38-7.47 (m, 2H), 7.51 (s, 1H), 7.81-7.87 (m, J=8.2 Hz, 2H), 7.96-8.03 (m, J=8.2 Hz, 2H), 9.32 (t, J=6.0 Hz, 1H); MS (ESI+) m/z 377.0 (M+H)+.
With triethylamine; HATU In N,N-dimethyl acetamide at 20℃; 1 In a 96 deep well plate, 4-(trifluoromethylthio)benzoic acid (23 mg, 0.10 mmol) was added dissolved in N,N-dimethylacetamide (0.4 mL), followed by O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATS) (48 mg, 0.12 mmol, 1.2 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), triethylamine (26 mg, 0.25 mmol, 2.4 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), and finally the amine (0.7 mL of a 0.2 M solution in N,N-dimethylacetamide, 1.4 equivalents). This was shaken at room temperature overnight. The reaction solution was concentrated to dryness in vacuo, dissolved in 1:1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC on a Phenomenex Luna Combi-HTS C8(2) 5µm 100Å (2.1mm × 30mm) using a gradient of 10-100% acetonitrile (A) and 0.1% trifluoroacetic acid (B) in water at a flow rate of 2.0 mL/minute (0-0.1 minutes 10% A, 0.1-2.6 minutes 10-100% A, 2.6-2.9 minutes 100% A, 2.9-3.0 minutes 100-10% A.) to give the product. The product was prepared from (3-(1H-pyrrol-1-yl)phenyl)methanamine according to Method A: 1H NMR (500 MHz, DMSO-d6) δ ppm 4.54 - 4.58 (m, 2 H), 6.28 (t, J=2.1 Hz, 2 H), 7.22 (d, J=6.4 Hz, 1 H), 7.32 (t, J=2.1 Hz, 2 H), 7.38 - 7.47 (m, 2 H), 7.51 (s, 1 H), 7.81 - 7.87 (m, J=8.2 Hz, 2 H), 7.96 - 8.03 (m, J=8.2 Hz, 2 H), 9.32 (t, J=6.0 Hz, 1 H); MS (ESI+) m/z 377.0 (M+H)+
  • 25
  • [ 1143624-67-2 ]
  • [ 330-17-6 ]
  • [ 1143624-81-0 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 3h; 2.A Example 2; Compound 1 of Table I; N-[6-(4-bromophenyl)-2-[(butyrylamino)methyl]-5-(2,4-dichlorophenyl)pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide; A) N-[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-(methoxymethyl)pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide; 18.0 g of the 1-[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-(methoxymethyl)pyrid-3-yl]methanamine obtained in step B) of Example 1 are dissolved in 200 ml of DCM, followed by addition of 8.38 g of 4-(trifluoromethylthio)benzoic acid, 19.1 ml of triethylamine and 19.63 g of PyBOP.The medium is stirred for 3 hours at room temperature and is then washed successively with 200 ml of 10% HCl, with 200 ml of aqueous 10% NaHCO3 solution, and then with 200 ml of distilled water.The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product. This product is purified by chromatography on silica, eluting with a DCM/MeOH gradient of from 0 to 1% MeOH over 1 hour.The fractions containing the purified product are combined and brought to dryness to give 18.0 g of expected product.LC/MS (Conditions C): MH+=654.8; rt=12.12 min
  • 26
  • [ 727385-55-9 ]
  • [ 330-17-6 ]
  • [ 1222868-43-0 ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere;
  • 27
  • [ 333-47-1 ]
  • [ 590-29-4 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
78% With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;
  • 28
  • [ 330-17-6 ]
  • N-(1-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-yloxy)-2-cyanopropan-2-yl)-4-(trifluoromethylsulfonyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid; potassium permanganate / water / 16 h / 20 °C 2.1: thionyl chloride / dichloromethane / 1 h / 60 °C 2.2: 20 °C
  • 29
  • [ 330-17-6 ]
  • 2-amino-3-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-methylpropanenitrile [ No CAS ]
  • N-(1-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-cyanopropan-2-yl)-4-(trifluoromethylthio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 4-(trifluoromethylthio)benzoic acid With thionyl chloride In dichloromethane at 60℃; for 1h; Stage #2: 2-amino-3-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-methylpropanenitrile With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; 18 Example 18 (S)-N-(1-((7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)-2-cyanopropan-2-yl)-4-((trifluoromethyl)thio)benzamide Example 18 (S )-N-( 1 -((7-chloro- 1 -hydroxy- 1.3 -dihydrobenzo [c] [ 1.2]oxaborol-6-yl)oxy )-2-cyanoprop an-2-ylV4-((trifluoromethyl)thio)benzamide A mixture of 4-((trifluoromethyl)thio)benzoic acid (1.84 g, 8.27 mmol) in DCM (20 mL) and SOCl2 (20 mL) is stirred at 60°C for lh. The solution is concentrated in vacuo to got the acyl chloride, which is added to a mixture of 2-amino-3-(7-chloro-l- hydroxy-l,3-dihydrobenzo[c][l,2]oxaborol-6-yloxy)-2-methylpropanenitrile (2.2 g, 8.27 mmol) and DIPEA (3.2 g, 24.8 mmol) in THF (50 mL). The mixture is stirred at rt overnight and concentrated. The residue is dissolved in EA (200mL), washed with brine (3 x 30mL), dried over Na2S04, concentrated under reduced pressure and purified by column chromatography to give the desired (N-(l-((7-chloro-l-hydroxy-l,3-dihydrobenzo [c] [ 1 ,2]oxaborole-6-yl)oxy) -2-cyanopropan-2-yl)-4-((trifluoromethyl)thio)benzamide as pale white solid (1.8g, yield 47%). :H NMR (400 MHz, DMSO-de): δ 9.18 (m, 2H), 7.96 (d, 2H), 7.86 (d, 2H), 7.33-7.32 (m, 2H), 4.92 (s, 2H), 4.57 (d, 1H), 4.40 (d, 1H), 1.86 (s, 3H) ppm; HPLC purity: 97.4% at 220 nm and 97.1% at 254 nm. MS: m/z = 471.1 (M+l, ESI+).
  • 30
  • [ 2314-97-8 ]
  • [ 1074-36-8 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
With tris(2,2'-bipyridyl)ruthenium dichloride; triethylamine In acetonitrile at 20℃; for 1h; Irradiation;
  • 31
  • [ 696-62-8 ]
  • [ 330-17-6 ]
  • 4'-methoxy-5-((trifluoromethyl)thio)-[1,1'-biphenyl]-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With palladium diacetate; caesium carbonate; N-acetyl-L-isoleucine; silver carbonate at 30℃; for 36h; Schlenk technique; Inert atmosphere;
  • 32
  • [ 150-13-0 ]
  • tetramethylammonium trifluoromethanethiolate [ No CAS ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
198 mg Stage #1: 4-amino-benzoic acid With tetrafluoroboric acid; tert.-butylnitrite In ethanol; water at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: tetramethylammonium trifluoromethanethiolate With copper(I) thiocyanate In acetonitrile at 20℃; for 1h; Inert atmosphere;
  • 33
  • [ 330-17-6 ]
  • 4-methoxy-N-(2-methoxyethyl)-2-(4-piperidylmethyl)-2H-indazol-5-carboxamide [ No CAS ]
  • [ 1442120-11-7 ]
YieldReaction ConditionsOperation in experiment
25 mg 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 N,N-dimethyl-formamide at 20℃; for 1h; 269 4-methoxy-N-(2-methoxyethyl)-2-[(1-{4-[(trifluoromethyl)sulphanyl]benzoyl}-piperidin-4-yl)methyl]-2H-indazole-5-carboxamide General procedure: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 25 mg of the title compound was obtained from 100 mg of the compound prepared in Example 266b and 96 mg of 4-[(trifluoromethyl)sulphanyl]benzoic acid in DMF. 1H-NMR (400 MHz, DMSO-d6): δ [ppm], 1.09-1.37 (2H), 1.38-1.72 (2H), 2.23-2.39 (1H), 2.70-2.93 (1H), 2.95-3.16 (1H), 3.30 (3H), 3.40-3.55 (5H), 4.20 (3H), 4.35 (d, 3H), 7.25 (1H), 7.46-7.58 (2H), 7.66 (1H), 7.78 (2H), 8.20 (1H), 8.82 (1H).
  • 34
  • [ 330-17-6 ]
  • [ 292638-85-8 ]
  • methyl 2-(3-oxo-6-((trifluoromethyl)thio)-1,3-dihydroisobenzofuran-1-yl)acetate [ No CAS ]
  • (E)-methyl 3-(1-(2-methoxy-2-oxoethyl)-3-oxo-6-((trifluoromethyl)thio)-1,3-dihydroisobenzofuran-4-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 42% 2: 46% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; potassium hydrogencarbonate; acetic acid In 1,2-dichloro-ethane at 60℃; for 24h; Schlenk technique; Inert atmosphere;
  • 35
  • [ 1442116-78-0 ]
  • [ 330-17-6 ]
  • [ 1442120-38-8 ]
YieldReaction ConditionsOperation in experiment
67 mg 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 N,N-dimethyl-formamide at 20℃; for 1h; 288 4-methyl-N-(2,2,2-trifluoroethyl)-2-[(1-{4-[(trifluoromethyl)sulphanyl]benzoyl}-piperidin-4-yl)methyl]-2H-indazole-5-carboxamide General procedure: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 67 mg of the title compound was obtained from 100 mg of 71a and 94 mg of 4-[(trifluoromethyl)sulphanyl]benzoic acid in DMF. 1H-NMR (400 MHz, DMSO-d6): δ [ppm], 1.12-1.35 (2H), 1.35-1.70 (2H), 2.21-2.40 (1H), 2.54 (3H), 2.70-2.88 (1H), 2.94-3.12 (1H), 3.38-3.61 (1H), 4.07 (2H), 4.36 (3H), 7.21 (1H), 7.37-7.60 (3H), 7.78 (2H), 8.55 (1H), 8.81 (1H).
  • 36
  • [ 524-38-9 ]
  • [ 330-17-6 ]
  • 1,3-dioxoisoindolin-2-yl 4-((trifluoromethyl)thio)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere;
  • 37
  • [ 330-17-6 ]
  • [ 1005206-25-6 ]
  • 38
  • (4-((trifluoromethyl)thio)phenyl)methanol [ No CAS ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
91% With diethylene glycol dimethyl ether at 70℃; for 0.666667h; Sonication; 22 Example 22: Preparation of 4-trifluoromethylthiobenzoic acid: In a 10 mL round bottom flask, 1.04 g of 4-trifluoromethylthiobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added, and the resulting mixture was placed in an ultrasonic reaction apparatus.40KHz/30W/70°C ultrasonic irradiation was allowed to open for 40 minutes.Diethylene glycol dimethyl ether was removed under reduced pressure and recrystallized to give 1.0 g of 4-trifluoromethylthiobenzoic acid (yield: 91%).
  • 39
  • [ 330-17-6 ]
  • [ 1204331-60-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: oxone / methanol; water / 102 h / 20 - 50 °C 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1.5 h 2.2: 20 °C
  • 40
  • [ 330-17-6 ]
  • N-{4-[1-(4-trifluoromethanesulfonyl-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzoyl}-guanidine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: oxone / methanol; water / 102 h / 20 - 50 °C 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1.5 h 2.2: 20 °C 3.1: hydrogen / palladium hydroxide, 20 wt% on carbon / ethanol / 16 h / Inert atmosphere
  • 41
  • [ 330-17-6 ]
  • 1-(4-(aminomethyl)phenyl)propan-1-one [ No CAS ]
  • N-(4-propionylbenzyl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 10h;
  • 42
  • [ 330-17-6 ]
  • methyl 4-(difluoro(trifluoromethyl)-λ4-sulfaneyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / 16 h / 80 °C / Inert atmosphere 2: potassium fluoride; trichloroisocyanuric acid; trifluoroacetic acid / acetonitrile / 18 h / 40 °C / Inert atmosphere; Sealed tube
  • 43
  • [ 330-17-6 ]
  • [ 98-80-6 ]
  • [ 41830-99-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(trifluoromethylthio)benzoic acid With potassium phosphate In 1,4-dioxane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With 2-chloro-1,3-dimethylimidazolinium chloride In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #3: phenylboronic acid With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90℃; for 16h; Inert atmosphere;
  • 44
  • [ 330-17-6 ]
  • [ 98-80-6 ]
  • (4-(difluoro(trifluoromethyl)-λ4-sulfaneyl)phenyl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium phosphate / 1,4-dioxane / 0.08 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 1.3: 16 h / 90 °C / Inert atmosphere 2.1: potassium fluoride; trichloroisocyanuric acid; trifluoroacetic acid / acetonitrile / 18 h / 40 °C / Inert atmosphere; Sealed tube
  • 46
  • [ 330-17-6 ]
  • [ 1612-76-6 ]
  • N-(5-phenyl-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Amide coupling of compounds: General procedure: A 20 mL screw caped vial, charged with the corresponding acid (0.5 mmol), amine (0.5 mmol), BOP reagent (1.4 mmol) and diisopropylethylamine (13 mmol) in anhydrous DMF solvent (3 mL) was stirred at room temperature for 16 h. After completion, the reaction mixture was concentrated under reduced pressure, followed by flash column chromatography (hexanes:ethyl acetate 80:20 to 60:40) give the desired product.
  • 47
  • [ 330-17-6 ]
  • 2-amino-5-(2-fluorophenyl)-1,3,4-oxadiazole [ No CAS ]
  • N-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 48
  • [ 330-17-6 ]
  • [ 2138-98-9 ]
  • N-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 49
  • [ 330-17-6 ]
  • 2-amino-5-(3'-fluorophenyl)-1,3,4-oxadiazole [ No CAS ]
  • N-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 50
  • [ 330-17-6 ]
  • [ 1673-45-6 ]
  • N-(5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 51
  • [ 330-17-6 ]
  • [ 1673-44-5 ]
  • N-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 52
  • [ 330-17-6 ]
  • [ 5711-64-8 ]
  • N-(5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 53
  • [ 330-17-6 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
  • 54
  • [ 33621-61-3 ]
  • [ 330-17-6 ]
  • N-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 55
  • 2-amino-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole [ No CAS ]
  • [ 330-17-6 ]
  • N-(5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 56
  • [ 5711-61-5 ]
  • [ 330-17-6 ]
  • N-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 57
  • [ 330-17-6 ]
  • [ 33621-60-2 ]
  • N-(5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 58
  • [ 330-17-6 ]
  • [ 49579-79-5 ]
  • N-(5-(4-isopropylphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 59
  • [ 60160-13-6 ]
  • [ 330-17-6 ]
  • N-(5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 60
  • [ 1016495-77-4 ]
  • [ 330-17-6 ]
  • N-(5-(3,5-dichlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 61
  • [ 330-17-6 ]
  • C9H8ClN3O2 [ No CAS ]
  • N-(5-(5-chloro-2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 62
  • [ 330-17-6 ]
  • [ 5711-72-8 ]
  • N-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
  • 63
  • [ 330-17-6 ]
  • C17H13ClF3NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium permanganate; acetic acid / water / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C
  • 64
  • [ 1074-36-8 ]
  • [ 2926-29-6 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
72% With tetrabutylammonium tetrafluoroborate; sodium bromide In acetonitrile at 20℃; for 10h; Electrolysis; Inert atmosphere;
  • 65
  • [ 330-17-6 ]
  • [ 330-14-3 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Acyl chlorides General procedure: The acid (5 mmol) was dissolved in anhydrous CH2Cl2 (10 mL) and DMF (a few drops) added.Oxalyl chloride (6 mmol, 1.2 equiv.) was added dropwise to the solution, that was cooled in an icewater bath. The resulting mixture was allowed to stir at room temperature for an additional 4 h andthe solvent was evaporated to afford the crude acyl chloride, which was used directly in the nextstep.
  • 66
  • [ 330-17-6 ]
  • N-phenethyl-N-(trifluoromethyl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0 - 20 °C 2: silver fluoride; pyridine / dichloromethane / 24 h / 20 °C / Sealed tube
  • 67
  • [ 128273-56-3 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4-phenylnaphthalene-1,2-dione; tetra-(n-butyl)ammonium iodide / acetonitrile; water / 24 h / 80 °C 2: tert.-butylhydroperoxide / water / 24 h / 80 °C
  • 68
  • [ 4021-50-5 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide In water at 80℃; for 24h;
  • 69
  • [ 330-17-6 ]
  • tetraethyl (((2-(3-aminophenyl)thieno[2,3-d]pyrimidin-4-yl)amino)methylene)bis(phosphonate) [ No CAS ]
  • (((2-(3-(4-((trifluoromethyl)thio)benzamido)phenyl)thieno[2,3-d]pyrimidin-4-yl)amino)methylene)bis(phosphonic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 20 °C 2: trimethylsilyl bromide / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C
  • 70
  • [ 330-17-6 ]
  • tetraethyl (((2-(3-aminophenyl)thieno[2,3-d]pyrimidin-4-yl)amino)methylene)bis(phosphonate) [ No CAS ]
  • C29H33F3N4O7P2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% 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; N,N-dimethyl-formamide at 20℃;
  • 71
  • [ 619-58-9 ]
  • [ 811-68-7 ]
  • [ 330-17-6 ]
YieldReaction ConditionsOperation in experiment
91% With silver hexafluoroantimonate; chloro[di(1-adamantyl)-2-dimethylaminophenylphosphine]gold(I) In 1,2-dichloro-ethane at 70℃; for 3h;
  • 72
  • [ 330-17-6 ]
  • [ 73183-34-3 ]
  • [ 1005206-25-6 ]
YieldReaction ConditionsOperation in experiment
70% With copper(I) tetrakis(acetonitrile)tetrafluoroborate; lithium perchlorate; sodium flouride; N-fluorobis(benzenesulfon)imide In acetonitrile for 6h; Irradiation; Inert atmosphere; Sealed tube;
  • 73
  • [ 330-17-6 ]
  • [ 940-76-1 ]
YieldReaction ConditionsOperation in experiment
63 %Spectr. With copper(I) tetrakis(acetonitrile)tetrafluoroborate; N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate; caesium fluoride In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;
  • 74
  • [ 330-17-6 ]
  • methyl 4,4-dimethyl-2-(4-((trifluoromethyl)thio)benzoyl)pentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 25 - 30 °C / Inert atmosphere 2: 4,4'-bis(carbomethoxy)-2,2'-bipyridine; Hantzsch ester; nickel(II) chloride ethylene glycol dimethyl ether complex / N,N-dimethyl acetamide / 24 h / 25 - 30 °C / Inert atmosphere; Sealed tube; Irradiation
  • 75
  • [ 142-08-5 ]
  • [ 330-17-6 ]
  • C13H8F3NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 25 - 30℃; Inert atmosphere;
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