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Structure of 171243-30-4
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CAS No. : | 171243-30-4 |
Formula : | C8H3ClF4O |
M.W : | 226.56 |
SMILES Code : | O=C(Cl)C1=CC(C(F)(F)F)=CC(F)=C1 |
MDL No. : | MFCD00061157 |
InChI Key : | BGAKSLBTFLVNAH-UHFFFAOYSA-N |
Pubchem ID : | 519364 |
GHS Pictogram: | ![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
* 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 |
---|---|---|
91% | With triethylamine; In chloroform; at 0 - 20℃; for 3.75h; | ) Compound 1.2 Acyl chloride 1.1 (5.00 g, 21.0 mmol) was added dropwise to an ice-cold solution of MeNH(OMe).HCl (2.80 g, 28.1 mmol) and Et3N (9.00 mL, 63.9 mmol) in CHCl3 (50 mL). The reaction mixture was stirred at 0C for 45 min and at room temperature for 3 h then was concentrated under reduced pressure. The residue was partitioned between water and EtOAc. The organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give compound 1.2 (4.78 g, 91% yield) as a brown oil. |
With triethylamine; In chloroform; at 0 - 20℃; for 1h; | Into a round-bottom flask equipped with a stir bar and nitrogen on demand were placed N,O-dimethylhydroxylamine hydrochloride (2.80 g, 28.7 mmol), Et3N (9.0 mL, 64.57 mmol) and CHCl3 (50 mL). The solution was cooled to 0C and 3-trifluoromethyl-5-fluorobenzoyl chloride (5.0 g, 22.07 mmol) was added dropwise over several minutes. The resulting solution was allowed to stir at 0C for 30 min, after which time it was allowed to warm to rt and stir for an additional 30 min. The mixture was then poured into a separatory funnel containing ethyl acetate and water. The organic layer was collected and was washed with water, brine, dried over MgSO4, filtered and the solvents were removed under reduced pressure to provide 68 as a clear oil which was used without any further purification. 1H NMR (CDCl3, 300 MHz) δ 7.83 (s, 1H), 7.65 (d, J= 9 Hz, 1H), 7.46 (d, J= 9 Hz, 1H), 3.59 (s, 3H), 3.42 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25℃; for 12h; | 2-Chloro-N-r5-fluorot3yridin-3-yl)-5-{r3-flυoro-5-rtrifluoromethyl)benzoyl1aminol- benzamide A solution of 5-amino-2-chloro-N-(5-fluoropyridin-3-yl)benzamide (Method 79; 124 mg, 0.466 mmol) and DlEA (405 μL, 2.33 mmol, 5.0 equiv) in THF (2.0 ml) was treated with 3-fluoro-5-(trifluorottiethyl)benzoyl chloride (131 mg, 0.582 mmol, 1.25 equiv). The reaction mixture was stirred for 12 h at 25 C. The reaction was quenched with 10% NaOH and extracted with EtOAc. The organics were dried with ΝaCl(sat) and then Na2SO4^) and removed under reduced pressure. The residue was purified directly by Gilson reverse phase preparatory Hl3LC (5-95% MeCN/H2O) to give 75 mg of product (35%). NMR: 11.11 (s, IH), 10.80 (s, IH), 8.68 (s, I H), 8.37 (s, IH), 8.18-8.12 (m, 3H), 8.03-7.93 (M, 3H), 7.63 (d, IH); m/z 456. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; | 3-(2-Pyridyl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole 3-Fluoro-5-trifluoromethylbenzoyl chloride (0.11 mL, 0.73 mmol) was added in a dropwise manner to a solution of pyridylamidoxime (99.3 mg, 0.73 mmol) in dichloromethane (10 mL) under argon. The reaction mixture was stirred at room temperature for 10 minutes and the solvent was removed in vacuo. DMF (4 ml) was added to the oily residue and the resulting solution was stirred at 120 C. for 16 h under argon. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo. Flash chromatography on silica gel (15%-20% ethyl acetate in hexanes) yielded 150 mg (66.9%, GC/MS product RT 7.59 min, 98% purity) of 3-(2-pyridyl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.86 (d, 1H), 8.40 (s, 1H), 8.24 (d, 1H), 8.18 (d, 1H), 7.90 (dt, 1H), 7.59 (d, 1H), 7.49 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; | 3-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-trifluoromethylphenyl)-1,2,4-oxadiazole 3-Fluoro-5-trifluoromethylbenzoyl chloride (0.10 mL, 0.65 mmol) was added to a solution of 5-fluoropyridylamidoxime (102.9 mg, 0.66 mmol) in dichloromethane (2 mL). The solution was stirred at room temperature for 10 minutes and then concentrated in vacuo. DMF (4 mL) was added to the residue and the resulting solution was stirred at 120 C. for 16 h under argon. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo. Flash chromatography on silica gel (10%-20% ethyl acetate in hexane) yielded 131.1 mg (62.5%, GC/MSproduct RT 7.34 min, 96% pure) of 3-(5-fluoro-2-pyridyl) -5-(3-fluoro-5-trifluoromethylphenyl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.70 (d, 1H), 8.38 (s, 1H), 8.28 (dd, 1H), 8.17 (d, 1H), 7.60 (dt, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In methanol; dichloromethane; chloroform; | EXAMPLE 240 Preparation of (R)-3-[N-(3-Fluoro-5-{trifluoromethyl)benzoyl}glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compound No. 1191) A solution of 3-fluoro-5-(trifluoromethyl)benzoyl chloride (0.058 mmol) in dichloromethane (1 mL) was added to a mixture of (R)-1-(3,5-dimethylisoxazol-4-ylmethyl)-3-(glycylamino)pyrrolidine (0.050 mmol) and piperidinomethylpolystyrene (58 mg) in chloroform (0.2 mL) and dichloromethane (0.75 mL). After the reaction mixture was stirred at room temperature for 2 h, methanol (1.0 mL) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was loaded onto Varian SCX column, and washed with CH3OH (16 mL). Product was eluted off using 2 N NH3 in CH3OH (6 mL) and concentrated to afford (R)-3-[N-(3-fluoro-5-(trifluoromethyl)benzoyl}glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compound No. 1191) (19.5 mg, 88%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 443.2 (M++H, C20H22F4N4O3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane; chloroform; | [Example 240] Synthesis of (R)-3- [N-(3-fluoro-5-(trifluoromethyl)benzoyl]glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compd. No. 1191) A dichloromethane solution (1 mL) of 3-fluoro-5-(trifluoromethyl)benzoyl chloride (0.058 mmol) was added to a solution of (R)-1-(3,5-dimethylisoxazol-4-ylmethyl)-3-(glycylamino)pyrrolidine (0.050 mmol) and a piperidinomethylpolystyrene (58 mg) in chloroform (0.2 mL) and dichloromethane (0.75 ml). The reaction mixture was stirred at room temperature for 2 hours, and methanol (1.0 mL) was then added. The resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was loaded onto a Varian SCX column and washed with methanol (16 mL). The obtained crude product was eluted with a solution of 2 M NH3in methanol (6 mL) and concentrated to provide (R)-3-[N-[3-fluoro-5-(trifluoromethyl)benzoyl]glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compd. No. 1191) (19.5 mg, 88%). The purity wasdetermined by RPLC/MS (100%). ESI/MS m/e 443.2 (M++H, C20H22F4N4O3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine; In dichloromethane; at 0℃; for 1.5h; | Method 19; Methyl 2-chloro-5-{r3-fluoro-5-(trifluoromethyl)benzoyl1amino}benzoate; To a solution of methyl 5-amino-2-chlorobenzoate (Method 24, 2.25 g, 12.1 mmol) and triethylamine (2.53 ml, 18.2 mmol) in DCM (15 ml) at O0C was added 3-fluoro-5-(trifluoromethyl)benzoyl chloride (3.02 g, 13.3 mmol). After 1.5 hours, the reaction mixture was diluted with DCM (100 ml), washed with IN HCl (30 ml), water (30 ml), brine (30 ml) and dried (MgSO4). The crude product was recrystallized from EtOAc:Hex (3 crops) to give 3.55 g (78%) white solid. <n="53"/>1H NMR CDCl3 8.05 (s, 1 H), 7.86 (m, 3 H), 7.79 (d, 1 H), 7.55 (d, 1 H), 7.48 (d, 1 H), 3.94 (S5 3 H); m/z: 374. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 0 - 25℃; for 16.75h; | Example 19 : 3-Fluoro-N- [4-methyl-3-(9H-pyrimido [4,5-b] indol-7-yl)phenyl] -5-(trifluoro- methyl)benzamideStep 1: 3-Fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide3-Iodo-4-methylaniline (2.42 g, 10.4 mmol) was dissolved in DCM (20.00 mL) and triethylamine (TEA) (1.70 mL, 12.2 mmol) was added and the resulting mixture was cooled to 0 0C. To the mixture was added dropwise 3-fluoro-5-(trifluoromethyl)benzoyl chloride (1.60 mL, 10.5 mmol) and the resulting mixture was stirred at 0 0C for 45 minutes and at 25 0C for 16 hours. The reaction was extracted with ethyl acetate and the organic extracts were washed with water sat. Na2CCh, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The reaction product was used in the next reaction without purification. 1H NMR(CDCl3): δ 8.98 (d, IH), 7.78 (s, IH), 7.72 (m, 2H), 7.55 (m, 2H), 7.23 (d, IH), 2.42 (s, 3H). MS (EI) m/z = 424 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; | To tert-Znrtyl 2-((R)-l-(5-((2R,5S)-2,5-dimethylpyrrolidine-l-carbonyl)-3-fluoropyridin-2- yl)ethylcarbamoyl)-2-ethylhydrazinecarboxylate (25 mg, 0.06 mmol) is added a solution of HCl in MeOH (3N, 1 mL). The reaction mixture is stirred at RT for 2 h and then concentrated <n="110"/>to dryness. No purification step is required, a he isolated hydrochloride is utilized in the next reaction.The hydrochloride (20 mg, 0.05 mmol) is dissolved in DMF (0.5 mL), treated withDIPEA (90 μL, 0.52 mmol) and 3-fluoro-5-(trifluoromethyl)benzoyl chloride (10 mg, 0.08 mmol) and stirred 2 h at RT. Then the mixture was concentrated in vacuo and the residue was purified by reversed phase HPLC using a gradient of ACN in water with 0.1% TFA to give the title compound. MS (m/z): 541.8 [M+H+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; | To (R)-tør/-butyl 2-(l -(2-chloro-4-(methoxycarbonyl)phenyl)ethylcarbamoyl)-2- ethylhydrazinecarboxylate (75 mg, 0.19 mmol) is added a solution of HCl in MeOH (3 N, 2 mL). The reaction mixture is stirred at RT for 14 h and then concentrated to dryness. No purification step is required, and the isolated title compound is utilized in the next reaction.The hydrochloride (63 mg, 0.19 mmol) is dissolved in DMF (1.0 mL), treated with DIPEA (163 μL, 0.94 mmol) and 3-fluoro-5-(trifluoromethyl)benzoyl chloride (47 mg, 0.21 mmol) and stirred 2 h at RT. Then the mixture was concentrated in vacuo and the residue was purified by chromatography on silica gel (n-hexan/EA). MS (m/z): 489.6 [M+H*] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; | 3-Fluoro-5-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 171243-30-4) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μL, 0.40 mmol) in THF (1 mL). After 2 h, an additional 25 μL of acyl chloride was added. The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane to yield the product as a waxy solid (45 mg, 57%). MS (ESI): m/z=470.0 [M+H]+. |
57% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; | 3-Fluoro-5-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 171243-30-4) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μ, 0.40 mmol) in THF (1 mL). After 2 h, an additional 25 of acyl chloride was added. The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33- 50% EtOAc in n-hexane to yield the product as a waxy solid (45 mg, 57%). MS (ESI): m/z = 470.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In dichloromethane; at 20℃; for 0.5h; | General procedure: To a solution of benzoyl chloride (1 mmol) in dry dichloromethane (10 ml) was added amine (1 mmol), and the mixture was stirred for 0.5 h at room temperature. After solvent evaporation, the crude product was purified by column chromatography on silica (CHCl3:CH3CH2OH = 9:1) resulting in yellow thick oil and crystallized from the dichloromethane-petroleum ether mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In dichloromethane; at 20℃; for 0.5h; | General procedure: To a solution of benzoyl chloride (1 mmol) in dry dichloromethane (10 ml) was added amine (1 mmol), and the mixture was stirred for 0.5 h at room temperature. After solvent evaporation, the crude product was purified by column chromatography on silica (CHCl3:CH3CH2OH = 9:1) resulting in yellow thick oil and crystallized from the dichloromethane-petroleum ether mixture. |
Tags: 171243-30-4 synthesis path| 171243-30-4 SDS| 171243-30-4 COA| 171243-30-4 purity| 171243-30-4 application| 171243-30-4 NMR| 171243-30-4 COA| 171243-30-4 structure
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P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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