Structure of 57631-05-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 57631-05-7 |
Formula : | C8H5F3N2 |
M.W : | 186.13 |
SMILES Code : | FC(F)(F)C1=NNC2=CC=CC=C12 |
MDL No. : | MFCD11111669 |
InChI Key : | PJVACBOIQLBALV-UHFFFAOYSA-N |
Pubchem ID : | 21407816 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With sodium nitrite; In water; acetic acid; | EXAMPLE 1 18.9 parts of 2-(2,2,2-trifluoro-ethyl)-aniline are dissolved in 700 parts by volume of glacial acetic acid. 14 parts by volume of a 50% aqueous solution of sodium nitrite are poured at one go into this well stirred solution. The temperature of the mass rises from 20 C. 27 C. The stirring is maintained at ambient temperature for about 15 hours, after which the intermediate diazo derivative has totally disappeared. A large part of the acetic acid is eliminated by distillation in vacuum so as to give a volume of about 100 parts. Then the solution is run into 160 parts of cold water with stirring. The precipitate of 3-trifluoromethyl-indazole formed is filtered off and washed with water: crude M.p. 98 C. It is recrystallized from boiling water for analysis. White needles of M.p. 104 C. (Kofler stage) are obtained; dry weight after recrystallisation 11.4 parts. the 2-(2,2,2-trifluoro-ethyl)-aniline is obtained in the following way: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With caesium carbonate;copper(l) iodide; dimethylaminoacetic acid; In dimethyl sulfoxide; at 190℃; for 0.5h;Microwave irradiation; | Example 17: 1 -({4-[3-(trifluoromethyl)-1 H-indazol-1 -yl]phenyl}methyl)-2- pyrrolidinone (E17); A mixture of 3-(trifluoromethyl)-1 H-indazole (D17) (75mg, 0.4mmol), 1-[(4- iodophenyl)methyl]-2-pyrrolidinone (D12) (120mg, 0.4mmol), cesium carbonate (261 mg, O.deltammol), copper (I) oxide (6mg, 0.04mmol) and N,N-dimethylglycine (8mg, O.Odeltammol) in dimethylsulfoxide (1.5ml) was stirred at 19O0C for 0.5 hours in a microwave reactor. The reaction mix was then partitioned between dichloromethane and water. The organic layer was added to a 5g isolute silica pre-packed column and eluted with 50:50 ethyl acetate / petroleum ether, material was further purified by mass directed auto-preparation to give the title compound as a yellow oil (13mg, 9%).1 H-NMR (400MHz, CDCI3) delta: 7.93 (1 H, dd, J=8Hz, & 1 Hz), 7.72 (3H, m), 7.52 (1 H, m), 7.45 (2H, d, J=8Hz), 7.37 (1 H, m), 4.55 (2H, s), 3.33 (2H, m), 2.49 (2H, t, J=8Hz), 2.05 (2H, m); LC/MS Retention time 3.29mins/(ES+) 360 (M+H, Ci9H16F3N3O requires 359). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine; In ethanol; at 20℃; | Description 17: 3-(trifluoromethyl)-1H-indazole (D17); A mixture of methyl-2-iodobenzoate (524mg, 2mmol), (trifluoromethyl) trimethylsilane (2mmol, 0.3ml) and oven dried cesium fluoride (2mg) was stirred at room temperature for 1 hour. The reaction mixture was then treated with 5N hydrochloric acid (0.5ml) and left to stir at room temperature for 18 hours. The reaction mixture was then dissolved in ethylene glycol dimethyl ether and stirred at 2O0C for 1 hour, then at 8O0C in a microwave reactor for 20 minutes and finally at 12O0C in a microwave reactor for 1 hour. The organic layer was separated from the reaction mixture and dried over sodium sulphate. The solvent was removed by rotary evaporation to give a yellow liquid (446mg) which was dissolved in ethanol (3ml) and treated with hydrazine hydrate (100mg, 2mmol, 0.1 ml). The mixture was stirred at room temperature overnight. The ethanol was removed by rotary evaporation and the residue partitioned between dichloromethane (5ml) and water (5ml). <n="39"/>The organic layer was added directly to a 5g isolute silica Sep-Pak column and eluted from 0-20% ethyl acetate in petroleum ether to give the title compound as a colourless oil (150mg, 40%).1 H-NMR (400MHz, CDCI3) delta: 10.47 (1 H, br s), 7.89 (1 H, m), 7.59 (1 H, m), 7.51 (1 H, m), 7.33 (1 H, m); LC/MS Retention time 2.72mins/(ES+) 185 (M-H, C8H5F3N2 requires 186). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 3-triflouromethylindazole (931 mg, 5.0 mmol) in dry DMF (15 mL) cooled to 0 C is treated with NaH (200 mg, 5.0 mmol, 60% in mineral oil). After stirring at 25 C for 2 h the mixture is cooled to 0 C and 2,4,5-dichloropyrimidine (745 mg, 5.0 mmol) is added. After stirring for 4 h the mixture is quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 20/1) to afford 1-(2-chloropyrimidin-4-yl)-<strong>[57631-05-7]3-trifluoromethyl-1H-indazole</strong> as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 3-triflouromethylindazole (931 mg, 5.0 mmol) in dry DMF (15 mL) cooled to 0 C is treated with NaH (200 mg, 5.0 mmol, 60% in mineral oil). After stirring at 25 C for 2 h the mixture is cooled to 0 C and 2,4,5-trichloropyrimidine (917 mg, 5.0 mmol) is added. After stirring for 4 h the mixture is quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 20/1) to afford 1-(2,5-dichloropyrimidin-4- yl)-<strong>[57631-05-7]3-trifluoromethyl-1H-indazole</strong> as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 3-triflouromethylindazole (931 mg, 5.0 mmol) in dry DMF (15 mL) cooled to 0 C is treated with NaH (200 mg, 5.0 mmol, 60percent in mineral oil). After stirring at 25 C for 2 h the mixture is cooled to 0 C and 2,4-dichloro-5-cyanopyrimidine (870 mg, 5.0 mmol) is added. After stirring for 4 h the mixture is quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 20/1) to afford the 1-(2-chloro-5- cyanopyrimidin-4-yl)-<strong>[57631-05-7]3-trifluoromethyl-1H-indazole</strong> as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 3-triflouromethylindazole (931 mg, 5.0 mmol) in dry DMF (15 mL) cooled to 0 C is treated with NaH (200 mg, 5.0 mmol, 60% in mineral oil). After stirring at 25 C for 2 h the mixture is cooled to 0 C and 2,4-dichloro-5-trifluoromethylpyrimidine (1.085 g, 5.0 mmol) is added. After stirring for 4 h the mixture is quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 20/1) to afford 1-(2-chloro-5-trifluoromethylpyrimidin-4-yl)-<strong>[57631-05-7]3-trifluoromethyl-1H-indazole</strong> as a white solid. |