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Structure of 922516-43-6
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CAS No. : | 922516-43-6 |
Formula : | C7H6ClF3N2O |
M.W : | 226.58 |
SMILES Code : | O=C(Cl)CN1N=C(C(F)(F)F)C=C1C |
MDL No. : | MFCD03421441 |
InChI Key : | ZCOXUPVESDJDHX-UHFFFAOYSA-N |
Pubchem ID : | 7015920 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H315-H318-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅲ |
* 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 oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h; | Step F: Preparation of 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l-acetyl chloride; 5-Methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetic acid (7.58 g, 36.4 mmol) (i.e. the product of Example 1, Step E) was dissolved in dichloromethane (100 mL). N^/V-dimethyl- formamide (1 drop) was added to the reaction mixture, which was then cooled to 0 C.Oxalyl chloride (3.5 mL, 40 mmol) was added drop wise to the stirred reaction mixture, which was then allowed to warm to room temperature for 3 h. The resulting mixture was concentrated under reduced pressure and placed under high vacuum to give 7.93 g of the title compound as a tan solid. This compound was of sufficient purity to use in subsequent reactions.1H NMR (CDCl3) delta 2.31 (s, 3H), 5.27 (s, 2H), 6.38 (s, IH). | |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h; | 5-Methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetic acid (7.58 g, 36.4 mmol) (i.e. the product of Example 2, Step A) was dissolved in 100 mL of dichloromethane. To the reaction mixture, 1 drop of lambdaf.lambdaf-dimethylformamide was added and the reaction mixture was cooled to 0 C. The reaction mixture was treated with oxalyl chloride (3.5 mL, 40 mmol) dropwise and allowed to warm to room temperature and stirred for 3 h. The resulting mixture was evaporated in vacuo and placed under high vacuum to give 7.93 g of the corresponding acid chloride, 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetyl chloride, as a tan solid. The acid chloride was dissolved in 50 mL of dichloromethane and a solution of ethyl 2-(4-piperidinyl)-4-thiazolecarboxylate monohydrochloride (10.38 g, 33.1 mmol) (i.e. the product of Example 19, Step A) and triethylamine (23 mL, 165 mmol) in 200 mL of dichloromethane was added at 0 C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into water and extracted with dichloromethane. The extract was washed with 1 M aqueous hydrochloric acid, water, saturated aqueous solution of sodium bicarbonate, and brine. The filtered mixture was dried (MgSC>4) and evaporated in vacuo to give 13.0 g of the title compound as an oil. 1H NMR (CDCl3) delta 1.4 (t, 3H), 1.78 (m, 2H), 2.2 (m, 2H), 2.32 (s, 3H), 2.80 (m, 1 H), 3.25 (m, IH), 3.36 (m, IH), 4.07 (m, IH), 4.42 (q, 2H), 4.62 (m, IH), 4.98 (m, 2H), 6.34 (s, IH), 8.09 (s, IH). | |
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃;Product distribution / selectivity; | Method A 2-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(2-phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (I-53) At 0 C., oxalyl chloride (134 mg) and a drop of N,N-dimethylformamide are added to a solution of <strong>[345637-71-0][5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid</strong> (185 mg) in dichloromethane. The reaction mixture is stirred at room temperature for 3 h. Solvent and excess reagent are removed under reduced pressure. The solid residue is then once more dissolved in dichloromethane and, at 0 C., added dropwise to a solution of 4-[4-(2-phenylethyl)-1,3-thiazol-2-yl]piperidine hydrochloride (II-1, 250 mg) and triethylamine (410 mg) in dichloromethane. Concentrated ammonium chloride solution is then added to the reaction solution, and the aqueous phase is removed and extracted with ethyl acetate. The combined organic phases are dried over anhydrous sodium sulphate and concentrated. This gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(2-phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (122 mg). 1H NMR (DMSO-d6): delta 7.28-7.26 (m, 2H), 7.22-7.21 (m, 2H), 7.19-7.15 (m, 2H), 6.51 (s, 1H), 5.33 (d, 1H), 5.25 (d, 1H), 4.36 (d, 1H), 3.95 (d, 1H), 3.35-3.20 (m, 2H), 2.96 (s, 4H), 2.82 (t, 1H), 2.21 (s, 3H), 2.09 (d, 1H), 2.07 (d, 1H), 1.78 (m, 1H), 1.53 (m, 1H) ppm MS (ESI): 463 ([M+H]+) |
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 0.25h;Reflux;Product distribution / selectivity; | Step B: Preparation of 4-(4-formyl-2-thiazolyl)-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine (also known as 2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxaldehyde) To a solution of <strong>[345637-71-0]5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid</strong> (0.8 g, 3.8 mmol) in dichloromethane (10 mL) was added oxalyl chloride (2.4 g, 19.2 mmol) and two drops of N,N-dimethylformamide, resulting in slight exothermicity. The reaction mixture was then heated at reflux for 15 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in tetrahydrofuran (10 mL) and treated with a solution of 2-(4-piperidinyl)-4-thiazolecarboxaldehyde monohydrochloride (i.e. the product of Example 2, Step A) (1.1 g, 5.1 mmol) in tetrahydrofuran (10 mL), followed by dropwise addition of triethylamine (1.2 g, 11.9 mmol). The reaction mixture was stirred overnight at room temperature and then partitioned between 1 N aqueous hydrochloric acid and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate (2*30 mL). The combined organic layers were washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure to give 0.8 g of the title compound as a yellow oil. 1H NMR (CDCl3): delta 1.79-1.90 (m, 2H), 2.18-2.29 (m, 2H), 2.33 (s, 3H), 2.87-2.94 (m, 1H), 3.28-3.40 (m, 2H), 4.05-4.15 (m, 1H), 4.56-4.64 (m, 1H), 4.99-5.02 (m, 2H), 6.35 (s, 1H), 8.12 (s, 1H), 10.01 (s, 1H). | |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 45℃; for 2h; | To a stirred solution of (5-methyl-3-trifluoromethyl-pyrazol-l-yl)acetic acid (0.0885 g, 0.4255 mmol) in dichloromethane (10 mL) was added oxalylchloride (0.108 g, 0.851 mmol) and drop a of DMF. The reaction mixture was stirred at 45 C for 2 h, and then concentrated under reduced pressure to provide the title compound as a white solid (0.096 g)..H NMR (CDCI3): delta 6.38 (s, 1H), 5.27 (s, 2H), 2.31 (s, 3H). | |
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 24h;Product distribution / selectivity; | Step 21-[4-(4-Acetyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (XXII-1)Oxalyl chloride (1.74 g) and a drop of N,N-dimethylformamide were added to a solution of <strong>[345637-71-0][5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid</strong> (1.00 g) in dichloromethane (10 ml). The reaction mixture was then stirred for 24 hours. Excess oxalyl chloride was then removed under reduced pressure, and the residue was redissolved in dichloromethane (10 ml). With cooling on an ice bath, the solution was then added to a suspension of 1-[2-(piperidin-4-yl)-1,3-thiazol-4-yl]ethanone hydrochloride (1.13 g) in dichloromethane (10 ml) and N,N-diisopropylethylamine (1.77 g). The reaction mixture was then allowed to warm to room temperature and stirred for another 2 hours. Saturated aqueous ammonium chloride solution (5 ml) was then added to the reaction mixture. The aqueous phase was separated off and extracted with dichloromethane. All organic phases were combined and dried with anhydrous sodium sulphate. The solid was then filtered off and the solvent was removed under reduced pressure. Purification by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient) gave 1-[4-(4-acetyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1.00 g).logP (pH2.7): 2.251H NMR (DMSO-d6, 400 MHz): deltappm. 1.65 (bs, 1H), 1.80 (bs, 1H), 2.18-2.11 (m, 2H), 2.23 (s, 3H), 2.55 (s, 3H), 2.90 (bs, 1H), 3.28 (bs, 1H), 3.39 (m, 1H), 4.00 (bs, 1H), 4.33 (bs, 1H), 5.22 (bs, 2H), 6.45 (s, 1H), 8.36 (s, 1H)MS (ESI): 401 ([M+H]+) | |
5.64 g | With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 16h; | Step A: Preparation of 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetyl chloride A mixture of 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetic acid (5.2 g, 25 mmol) in dichloromethane (70 mL) and N,N-dimethylformamide (2 drops) was cooled to 0 C and oxalyl chloride (4.76 g, 37.5 mmol) in dichloromethane (10 mL) was added dropwise. The reaction mixture was stirred at room temperature for 16 h, and then concentrated under reduced pressure to give the title compound as a slightly yellowish solid (5.64 g). H NMR (CDC13): delta 6.38 (s, 1H), 5.27 (s, 2H), 2.31 (s, 3H). |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 0.25h;Heating / reflux;Product distribution / selectivity; | To a solution of 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetic acid (0.8 g, 3.8 mmol) in dichloromethane (10 mL) was added oxalyl chloride (2.4 g, 19.2 mmol) and two drops of iV.TV-dimethylformamide, resulting in slight exothermicity. The reaction mixture was then heated at reflux for 15 minutes. The reaction mixture was concentrated in vacuo, and the residue was suspended in tetrahydrofuran (10 mL) and treated with a solution of 2-(4-piperidinyl)-4-thiazolecarboxaldehyde' monohydrochloride (i.e. the product of Example 2, Step A) (1.1 g, 5.1 mmol) in tetrahydrofuran (10 mL), followed by dropwise addition of triethylamine (1.2 g, 11.9 mmol). The reaction mixture was stirred overnight at room temperature and then partitioned between 1 N aqueous hydrochloric acid and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate (2 x 30 mL). The combined organic layers were washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was dried (MgSC^) and evaporated under reduced pressure to give 0.8 g of the title compound as a yellow oil. <n="79"/>IH NMR (CDCl3) delta 1.79-1.90 (m, 2H)5 2.18-2.29 (m, 2H), 2.33 (s, 3H), 2.87-2.94 (m, IH)5 3.28-3.40 (m, 2H), 4.05-4.15 (m, IH), 4.56-4.64 (m, IH), 4.99-5.02 (m, 2H), 6.35 (s, IH), 8.12 (s, IH)5 IO-Ol (s, IH).; To a solution of 5-methyl-3-(trifluoromethyl)-li'-pyrazole-l -acetic acid (0.5 g,2.4 mmol) in dichloromethane (4 mL) was added oxalyl chloride (0.3 mL, 3.6 mmol) and one drop of N,LambdaT-dimethylformamide, resulting in slight exothermicity. The reaction mixture was then heated at reflux for 15 minutes. The reaction mixture was evaporated, and the resulting residue was suspended in dichloromethane (4 mL) and treated with a solution of 4-(4-ethenyl-2-thiazolyl)piperidine (i.e. the product of Example 4, Step B) (302 mg,1.5 mmol) in dichloromethane (2 mL), followed by addition of triethylamine (0.32 mL, 2.3 mmol). The reaction mixture was stirred overnight at room temperature, then concentrated, and purified by column chromatography on silica gel using 30-40 % ethyl acetate in hexanes as eluant to give 414 mg of the title compound as a white solid. IH NMR (CDCl3) 6 1.78 (m, 2H), 2.18 (m, 2H), 2.32 (s, 3H), 2.90 (br t, IH), 3.30 (m, 2H),4.03 (d, IH), 4.55 (d, IH), 5.00 (m, 2H), 5.35 (d, IH), 6.02 (d, IH), 6.33 (s, IH), 6.68 (dd,IH)5 7.01 (s, IH). | |
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h; | Step B: Preparation of ethyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylate. 5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (7.58 g, 36.4 mmol) (i.e. the product of Example 2, Step A) was dissolved in 100 mL of dichloromethane. To the reaction mixture, 1 drop of N,N-dimethylformamide was added and the reaction mixture was cooled to 0 0C. The reaction mixture was treated with oxalyl chloride (3.5 mL, 40 mmol) dropwise and allowed to warm to room temperature and stirred for 3 h. The resulting mixture was evaporated in vacuo and placed under high vacuum to give 7.93 g of the corresponding acid chloride, 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l-acetyl chloride, as a tan solid. The acid chloride was dissolved in 50 mL of dichloromethane and a solution of ethyl 2-(4-piperidinyl)-4-thiazolecarboxylate monohydrochloride (10.38 g, 33.1 mmol) (i.e. the product of Example 19, Step A) and triethylamine (23 mL, 165 mmol) in 200 mL of dichloromethane was added at 0 0C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into water and extracted with dichloromethane. The extract was washed with 1 M aqueous hydrochloric acid, water, saturated aqueous solution of sodium bicarbonate, and brine. The filtered mixture was dried (MgSC^) and evaporated in vacuo to give 13.0 g of the title compound as an oil. EPO <DP n="85"/>1H NMR (CDCl3) delta 1.4 (t, 3H), 1.78 (m, 2H), 2.2 (m, 2H), 2.32 (s, 3H), 2.80 (m, 1 H), 3.25 (m, IH), 3.36 (m, IH), 4.07 (m, IH), 4.42 (q, 2H), 4.62 (m, IH), 4.98 (m, 2H), 6.34 (s, IH),8.09 (s, IH). |
Tags: 922516-43-6 synthesis path| 922516-43-6 SDS| 922516-43-6 COA| 922516-43-6 purity| 922516-43-6 application| 922516-43-6 NMR| 922516-43-6 COA| 922516-43-6 structure
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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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The concentration of the dissolution solution you need to prepare is mg/mL