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CAS No. : | 161622-05-5 | MDL No. : | MFCD00061293 |
Formula : | C8H4F4O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | NSGKIIGVPBTOBF-UHFFFAOYSA-N |
M.W : | 208.11 | Pubchem ID : | 519222 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
te?'/-butyl 4-fluoro-4-rf3-fluoro-5-('trifluoromethyl')benzamido')methyl)piperidine-l-carboxylate (3-5'); 1-Hydrozybenzotriazole (0.973 g, 7.2 mmol) and 3-fluoro-5-(trifluoromethyl)benzoic acid (1.25 g, 6.0 mmol) were suspended in 30 mL diy CH2Cl2. Diisopropylethylamine (2.1 mL, 12.0 mmol) was added and all compounds went into solution. Amine 3-4 (1.39 g, 6.0 mmol) was added in 30 mL dry CH2Cl2. PS-carbodiimide resin (7.5 g, 12.0 mmol) was then added and the mixture was vigorously stirred overnight. MP-carbonate resin (4.Og, 12.0 mmol) was added and stirring was resumed for 3 h. The reaction was then filtered to remove resin and concentrated in vacuo. A 40 g SiO2 column was run in 0-50% EtOAc/hexanes, yielding 902 mg of 3-5 (36% over 3 steps) as a viscous yellow oil. 1H NMR (CDCl3, 300 MHz): 7.84 (s, IH), 7.73 (d, J= 8.4 Hz, IH), 7.45 (d, J= 8.4 Hz, IH), 3.92 (br, 2H), 3.65 (m, 2H), 3.10 (m, 2H), 1.68 (m, 4H), 1.43 (s, 9H); MS (Electrospray): m/z 445.2 (M+Na), 367.1 (M- t-Bu+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; | A mixture of 4-Methyl-N*3*- (4-pyrazin-2-yl-pyrimidin-2-yl)-benzene-1, 3-diamine (0.55 g, 1.98 MMOL), 3-Fluoro-5-trifluoromethyl-benzoic acid (0.43 g, 2.08 MMOL), BOP (1.05 g, 2.38 MMOL) and DIEA (1.25 mL, 7.20 MMOL) is stirred in 9.0 mL of DMF at room temperature overnight. 25 mL of water is added to the precipitate. The resulting suspension is allowed to stir at room temperature for one hour. It is then filtered through a Buchner funnel, air dried and triturated with 10.0 mL of CH30H for 1 hour and dried. 0.80 g of 3-FLUORO-N- [4-METHYL-3- (4-PYRAZIN-2- yl-pyrimidin-2-ylamino)-phenyl]-5-trifluoromethyl-benzamide is obtained as a pale yellow solid. RH NMR (DMSO, 500MHZ) : No. (ppm) 10.49 (s, 1H), 9.49 (s, 1H), 9.10 (s, 1H), 8.79 (s, 2H), 8. 62 (d, 2H, J=4.81 Hz), 8.10-8. 20 (m, 3H), 7.96 (d, 1H, J=8.66Hz), 7. 63 (d, 1H, J=4. 78Hz), 7.48 (dd, 1H, J1=8. 46Hz, J2=2. 05 HZ), 7.26 (d, 1H, J=8.09Hz), 2.26 (s, 3H). API-MS m/z 469.1 ([M+H] +, CALCD 469.1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 34 5-Fluoro-3-trifluoromethylbenzoylguanidine hydrochloride Colorless crystals, m.p. 150-51 C. from 5-fluoro-3-trifluoromethylbenzoic acid following the general protocol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | 1 g (4.8 mmol) of <strong>[161622-05-5]3-trifluoromethyl-5-fluorobenzoic acid</strong> was dissolved in 10 mL of dimethylformamide, then 623 mg (5.76 mmol) of benzyl alcohol was added thereto dropwise. 423 mg (60%, 10.5 mmol) of sodium hydride was slowly added to the reaction solution at 0C, and stirred for 10 minutes, then the solution was heated at 50 C for 4 hours. The reaction solution was diluted with ethyl acetate and washed with water, and then dried over anhydrous magnesium sulfate. Solvent was removed and the residue was purified by column chromatography to obtain 825 mg of the title compound in a yield of 58%.NMR: 1H-NMR(CDCl3) delta 7.95(1H, s), 7.85(1H, s), 7.50~7.30(6H, m), 5.13(2H, s)Mass(EI) 297 (M++l) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With pyridine; HATU; In N,N-dimethyl-formamide; for 16h; | Example 25; 5-[3-Fluoro-5-Ctrifluoromethyl)benzoyl1amino}-2-methyl-N-(2-methyl-l,3-thiazol-5- vDbenzamide; To a solution of 5-amino-2-methyl-N-(2-methyl-l,3-thiazol-5-yl)benzamide (Method25, 100 mg, 0.40 mmol) and <strong>[161622-05-5]3-fluoro-5-(trifluoromethyl)benzoic acid</strong> (85 mg, 0.40 mmol) in anhydrous DMF (5 ml) was added HATU (154 mg, 0.40 mmol) and pyridine (5 eq.). After stirring for 16 hours, the reaction mixture was diluted with EtOAc, washed with water, dried (Na2SO4) and concentrated. Purification by column chromatography (Hex:EtOAc) gave 10 121mg (68%) of a white solid.1H NMR Acetone-d6 10.70 (s, 1 H) 9.94 (s, 1 H) 8.19 (s, 1 H) 8.08 (s, 1 H) 8.04 (d, 1 H) 7.80 (dd, 2 H) 7.49 (s, 1 H) 7.32 (d, 1 H) 2.60 (s, 3 H) 2.43 (s, 3 H); m/z: 438. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 64 (General Procedure (D)) N-(3,5-Bis-Trifluoromethyl-Phenyl)-3-Fluoro-5-Trifluoromethyl-Benzamide. The title compound was prepared from <strong>[161622-05-5]3-fluoro-5-trifluoromethyl-benzoic acid</strong> and 3,5-Bis-trifluoromethylanilin. 1H NMR (DMSO-d6): delta ppm 7.88 (m, 1 H) 8.04 (d, 1 H) 8.15 (d, 1 H) 8.22 (m, 1 H) 8.48 (m, 2 H) 11.04 (s, 1 H); HPLC-MS (Method A): m/z=420 (M+1); Rt=5.5 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 65 (General Procedure (D)) 3-Fluoro-N-(4-Nitro-3-Trifluoromethyl-Phenyl)-5-Trifluoromethyl-Benzamide. The title compound was prepared from <strong>[161622-05-5]3-fluoro-5-trifluoromethyl-benzoic acid</strong> and 4-nitro-3-trifluoromethylanilin. 1H NMR (DMSO-d6): delta ppm 8.05 (d, 1 H) 8.16 (d, 1 H) 8.21 (s, 1 H) 8.32 (m, 2 H) 8.43 (d, J=1.88 Hz, 1 H) 11.18 (s, 1 H); HPLC-MS (Method A): m/z=397 (M+1); Rt=5.0 min. |
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