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[ CAS No. 97914-59-5 ] {[proInfo.proName]}

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Chemical Structure| 97914-59-5
Chemical Structure| 97914-59-5
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Product Details of [ 97914-59-5 ]

CAS No. :97914-59-5 MDL No. :MFCD00236223
Formula : C8H6F2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AGDOJFCUKQMLHD-UHFFFAOYSA-N
M.W : 188.13 Pubchem ID :2063348
Synonyms :

Safety of [ 97914-59-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 97914-59-5 ]

* 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 [ 97914-59-5 ]

[ 97914-59-5 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 67-56-1 ]
  • [ 97914-59-5 ]
  • [ 97914-53-9 ]
YieldReaction ConditionsOperation in experiment
87% sulfuric acid;Heating / reflux; a) 2-Difluoromethoxy-benzoic acid methyl ester2.0 g of 2-difluoromethoxy-benzoic acid (10.6 mmol, 1.0 eq) were dissolved <n="137"/>in MeOH (15 mL) and a catalytic quantity of sulfuric acid was added; the mixture was heated at reflux overnight. The solvent was then evaporated and the residue was dissolved in DCM and washed with saturated NaHCO3. The organic phase was dried and evaporated to give 1.9 g of title product (yield 87%).C9H8F2O31H-NMR (dmso-d6): 3.82 (3H, s); 6.99-7.40 (2H5 m); 7.31 (IH, d, J=8.4 Hz); 7.63-7.67 (IH5 m); 7.82-7.84 (IH5 m).
  • 2
  • [ 444287-40-5 ]
  • [ 97914-59-5 ]
  • [ 927671-99-6 ]
YieldReaction ConditionsOperation in experiment
65% 5.143 2-DIFLUOROMETHOXY-N-[2-(2,6-DIOXO-PIPERIDIN-3-YL)-1,3-DIOXO-2,3-DIHYDRO-1H-ISOINDOL-4-YLMETHYL]-BENZAMIDE To a stirred suspension of 4-aminomethyl-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (0.70 g, 2.2 mmol) in CH3CN (60 ml), was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.82 g, 5.4 mmol). After stirring for 10 minutes, 1-hydroxybenzenetriazole (0.35 g, 2.6 mmol) and 2-difluoromethoxy benzoic acid (0.45 g, 2.4 mmol) were added, followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.62 g, 3.2 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated in vacuo, and the residue was dissolved in CH2Cl2 (50 mL). The CH2Cl2 solution was then washed with water (2×30 mL) and brine (30 mL), and dried over MgSO4. Solvent was removed in vacuo, and the resulting oil was purified by ISCO silica gel flash chromatography (eluent: 0% MeOH in CH2Cl2 to 5% MeOH in 10 min then stay at this ratio for 15 min) to afford 4-difluoromethoxy-N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-benzamide as a solid (0.64 g, 65%): mp, 164-166 C.; HPLC: Waters Symmetry C-18, 3.9×150 mm, 5 micro, 1 mL/min, 240 nm, 40/60 (CH3CN/H2O): tR=3.6 (99%); 1H NMR (DMSO-d6): δ 2.04-2.09 (m, 1H), 2.53-2.64 (m, 2H), 2.85-2.93 (m, 1H), 4.92 (d, J=6.0 Hz, 2H), 5.14-5.20 (dd, J=5, 12 Hz, 1H), 6.97-7.86 (m, 8H), 8.97 (t, J=5.8 Hz, 1H), 11.15 (s, 1H). 13C NMR (DMSO-d6) δ: 21.95, 30.91, 38.29, 48.86, 113.18, 116.60, 119.08, 120.02, 121.91, 125.34, 127.12, 128.74, 129.58, 131.48, 131.54, 132.96, 134.64, 138.89, 147.66, 165.60, 166.94, 167.51, 169.80, 172.73. Anal Calcd for C22H17F2N3O6: C, 57.77; H, 3.75; N, 9.19; F, 8.31. Found: C, 57.62; H, 3.60; N, 8.99; F, 8.32.
  • 3
  • [ 1000387-18-7 ]
  • [ 97914-59-5 ]
  • [ 1000387-24-5 ]
YieldReaction ConditionsOperation in experiment
Intermediate 17: 5-Amino-λ/-(2-r(((2-r(difluoromethv?oxylphenyl|carbonyl)(2-r(1.1- dimethylethv?oxy1ethyl}amino)methyl1-3,3,3-trifluoro-2-hvdroxypropyl>-1-(4-fluorophenv?- 1/-/-pyrazole-4-carboxamide; solution of O-(7-azabenzotriazol-1 -yl)-N,N, N', N'-tetramethyluronium hexafluorophosphate (HATU) (498.1 mg, 1.31 mmol) in dimethylformamide (2.5ml) was added to 2-difluoromethoxybenzoic acid (246.3mg, 1.31 mmol ). After 10 minutes, a solution of 5-amino-λ/-{2-[({2-[(1 ,1-dimethylethyl)oxy]ethyl}amino)methyl]-3,3,3-trifluoro-2- hydroxypropyl}-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxamide (550mg, 1.19mmol) and diisopropylethylamine (461.6mg, 3.57mmol) in dimethylformamide (2.5ml) was added and the solution was stirred under nitrogen at room temperature. After 3.5 hours, the reaction mixture was concentrated in vacuo and the residue was purified by the Flashmaster with 0-100% ethyl acetate in cyclohexane gradient over 60 minutes as eluent. This gave the title product (423mg).1H NMR (400 MHz, CHLOROFORM-cQ δ ppm 7.74 (s, 1 H) 7.47 (s, 2H) 7.42 (s, 3H) 7.25 - 7.31 (m, 1 H) 7.13 - 7.24 (m, 2H) 5.52 (br. s., 2H) 3.15 - 4.24 (m, 9H) 1.13 (s, 9H). LC-MS Retention Time 3.37mins, MH+ 631.
  • 4
  • [ 97914-59-5 ]
  • [ 1608129-74-3 ]
  • 5
  • [ 97914-59-5 ]
  • [ 1608129-59-4 ]
  • 6
  • [ 97914-59-5 ]
  • 4-pyrrolidin-1-yl-piperidine-1-carboxylic acid [5-(2-difluoromethoxyphenyl)-2H-pyrazol-3-yl]amide formate salt [ No CAS ]
  • 7
  • [ 97914-59-5 ]
  • [ 1016690-71-3 ]
  • 8
  • [ 97914-59-5 ]
  • [ 1608129-78-7 ]
  • 9
  • [ 97914-59-5 ]
  • [ 1040724-27-3 ]
  • 10
  • [ 97914-59-5 ]
  • [ 1040721-25-2 ]
  • 11
  • [ 97914-59-5 ]
  • [ 1040721-31-0 ]
  • 12
  • [ 97914-59-5 ]
  • 4-(2-amino-3-methylbutanoyl)benzonitrile hydrochloride [ No CAS ]
  • N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-yl)-2-(difluoromethoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% 2-(Difluoromethoxy)benzoic acid (CAS 97914-59-5, 33.1 mg, 0.18 mmol) was dissolved in DMF (200 iL). HBTU (83 mg, 0.22 mmol) and TEA (61.1 iL, 0.44 mmcl) were added. The solution was stirred for 6 mm before 4-(2-amino-3-methylbutanoyl)benzonitrile hydrochloride (Example 49b, 35 mg, 0.15 mmol) in DMF (400 iL) and TEA (61.1 iL, 0.44 mmol) was added. The reaction mixture was stirred for 1 h at rt before purified bypreparative HPLC to give N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-yl)-2- (difluoromethoxy)benzamide (46.7 mg, 86%).1H NMR (500 MHz, CDCI3) 5 ppm 0.88 (d, 3 H) 1.09 (d, 3 H) 2.27 (m, 1 H) 5.74 (dd, 1 H) 6.53 -6.92 (m, 1 H) 7.19 (d, 1 H) 7.29 - 7.36 (m, 1 H) 7.47 - 7.55 (m, 1 H) 7.75 (d, 1 H) 7.82 (d, 2 H)8.06 (dd, 1 H) 8.14 (d, 2 H).MS (ESI) m/z 370.8 [M-H]
  • 13
  • [ 97914-59-5 ]
  • C12H15N3O [ No CAS ]
  • C20H19F2N3O3 [ No CAS ]
  • 14
  • [ 97914-59-5 ]
  • 2-(2-(1,4-diazepan-1-yl)-5-methyloxazol-4-yl)propan-2-ol [ No CAS ]
  • (2-(difluoromethoxy)phenyl)(4-(4-(2-hydroxypropan-2-yl)-5-methyloxazol-2-yl)-1,4-diazepan-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
20 mg Step 6: (2-(difluoromethoxy)phenyl)(4-(4-(2-hydroxypropan-2-yl)-5-methyloxazol-2-yl)-l,4- diazepan-l-yl)methanone (Example 12) To a solution of 2-(difluoromethoxy) benzoic acid (31 mg, 0.15 mmol) in DMF (2 mL) was added HATU (57 mg, 0.15 mmol) and DIPEA (0.088 mL, 0.50 mmol). After stirring at room temperature for 10 min, 12-5 (30 mg, 0.125 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was purified by preparative HPLC to give Example 12 (20 mg) as a white solid. LRMS m/z (M+H) 410.1 found, 410.2 required.
  • 15
  • [ 97914-59-5 ]
  • N-(((3aS,6R,6aR)-6-(aminomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-3a(4H)-yl)methyl)benzamide [ No CAS ]
  • N-(((3aR,4R,6aS)-6a-(benzamidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-2-(difluoromethoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere; General procedure: To a solution of the crude amine, obtained via general procedure1, in DMF (25 mL/mmol) were added the appropriate organicacid (1.5 equiv per amine), EDCHCl (2 equiv per amine), diisopropylethylamine(4 equiv per amine) and a catalytic amount of1-hydroxybenzotriazole. The reaction mixture was stirred 16 h atrt. The mixture was concentrated and partitioned between waterand EtOAc. The organic layer was dried over sodium sulphate, filteredand concentrated in vacuo. The products were purified bycolumn chromatography with appropriate eluents.
  • 16
  • [ 97914-59-5 ]
  • 2-(difluoromethoxy)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% 2- (difluoromethoxy) benzoic acid (400 mg, 2.13 mmol) in methanol (15 ml) solution was added dropwise concentrated sulfuric acid (64 μl). Under an argon atmosphere, and stirred under reflux conditions overnight. After completion of the reaction, concentrated to dryness. Saturated saline, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with chloroform. Dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.ResidueIn ethanol (6 ml) solution,Hydrazine monohydrate (827 μl, 17.0 mmol) was added dropwise. Under an argon atmosphere, was stirred for 4 hours at reflux conditions, it was solidified after completion of the reaction concentrated to dryness. The residue was purified by silica gel column chromatography (chloroform / methanol) to give the title compound (180 mg, 42%)
  • 17
  • [ 97914-59-5 ]
  • 2-(2-(difluoromethoxy)phenyl)-1,3,4-oxadiazole [ No CAS ]
  • 18
  • 1-(difluoromethoxy)-3-methyl-6-nitro-4-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate [ No CAS ]
  • [ 65-85-0 ]
  • [ 97914-59-5 ]
  • [ 4837-20-1 ]
  • [ 4837-19-8 ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 23℃; for 12h;Irradiation; Glovebox; Sealed tube; Inert atmosphere; General procedure: In a glovebox, to an oven-dried 20 mL screw cap vial was added 1- (difluoromethoxy) -3-methyl-6-nitro-4- (trifluoromethyl) -lff- benzo [d] [1, 2, 3] triazol-3-ium trifluoromethanesulfonate (la) (92.4 mg, 0.200 mmol, 1.00 equiv), (hetero) arene (2.00 mmol, 10.0 equiv), Ru (bpy) 3 (PF6) 2, (0.860 mg, 1.00 pmol, 0.500 mol%), and MeCM (1.00 mL, 0.200 M, with respect to la) . To this suspension or solution was added a magnetic stir bar. Next, the reaction vial was capped and taken out of the glovebox. The reaction mixture was stirred at ambient temperature (23 C) and irradiated with blue LEDs (30 W, Xmax = 450 nm) which was placed 20.0 m from the vial for 12 h. To determine the yield of the products, an internal standard, trifluorotoluene (PhCF3) (14.6 mg, 12.3 pL, 0.100 mmol, 0.500 equiv) was added to the vial. Then, a 100 pL of the reaction mixture was taken and then dilute with 500 pL CD3CN followed by 19F NMR (the NMR sample was recombined with the rest of the reaction mixture afterward) . The combined reaction mixture was then purified by HPLC on the Luna PFP(2) preparative column (250 x 21.2 mm) column eluting with MeCN:H20 (v/v) with a flow rate of 10.6 mL/min to provide the purified products. In cases of closely-eluting peaks, products were isolated as a mixture of isomers. Afterwards, the products were extracted with CDC13 (3 x 1 mL) , dried with magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford the desired product (s). For very volatile compounds, the products were extracted immediately with CDCI3 (l x l mL) and then directly characterized. 1H and 13C NMR of these Compound (s) contains MeCN residue signal (1H NMR: □ 1.94, 13C NMR: u 118.26, 1.32 in CDCI3 )
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