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[ CAS No. 155377-19-8 ]

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Chemical Structure| 155377-19-8
Chemical Structure| 155377-19-8
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CAS No. :155377-19-8MDL No. :MFCD00052083
Formula : C7H7F3N2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :208.14Pubchem ID :596095
Synonyms :

Computed Properties of [ 155377-19-8 ]

TPSA : 55 H-Bond Acceptor Count : 6
XLogP3 : 1.4 H-Bond Donor Count : 1
SP3 : 0.43 Rotatable Bond Count : 3

Safety of [ 155377-19-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 155377-19-8 ]

  • Upstream synthesis route of [ 155377-19-8 ]
  • Downstream synthetic route of [ 155377-19-8 ]

[ 155377-19-8 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 74-88-4 ]
  • [ 155377-19-8 ]
  • [ 111493-74-4 ]
YieldReaction ConditionsOperation in experiment
81.7%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333 h;
Stage #2: at 0℃; for 18 h;
Dissolve 3 -trifluoromethyl- lH-pyrazole-4-carboxylic acid ethyl ester (2.0 g, 9.61 mmol) in N,N-dimethylformamide (20 mL) and cool to 0 0C. Add sodium hydride (0.58 g, 14.42 mmol, 60percent dispersion in oil) and stir at 0 0C for 20 min. Add iodomethane (0.90 mL, 14.42 mmol) and allow to warm to room temperature over 18 hr. Partition between ethyl acetate (100 mL) and water (50 mL). Separate the organic layer and wash with water (5 x 50 mL) and saturated aqueous sodium chloride solution (50 mL). Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 90: 10 hexanes: ethyl acetate), to give 1 -methyl-3 -trifluoromethyl- lH-pyrazole-4- carboxylic acid ethyl ester (1.74 g, 81.7percent). 1H-NMR (400 MHz, CDCl3) δ 7.92 (s, IH), 4.27 (q, 2H), 3.95 (s, 3H), 1.33 (t, 3H).
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4569 - 4574[2] Angew. Chem., 2017, vol. 129, # 16, p. 4640 - 4645,6
[3] Patent: WO2008/141020, 2008, A1, . Location in patent: Page/Page column 50
[4] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
  • 2
  • [ 77-78-1 ]
  • [ 155377-19-8 ]
  • [ 111493-74-4 ]
Reference: [1] Molecules, 2015, vol. 20, # 3, p. 4383 - 4394
  • 3
  • [ 512-56-1 ]
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YieldReaction ConditionsOperation in experiment
86% at 180℃; for 16 h; Example P2: Preparation of S-trifluoromethyl-i-methyl-I H-pyrazole^-carboxylic acid ethyl ester:A mixture of 4.16 g of S-trifluoromethyl-IH-pyrazole^-carboxylic acid ethyl ester (20 mmol) and 10 ml of trimethyl phosphate (86.4 mmol) is stirred at a temperature of 1800C for 16 hours. 200 ml of an ice-water mixture are then added. The resulting reaction product is filtered, washed with water and dissolved in 50 ml of ethyl acetate. The organic phase is washed twice with 50 ml of saturated sodium chloride solution each time and dried over sodium sulfate and concentrated by evaporation. 4.0 g (90 percent of theory) of 3-trifloromethyl- 1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester are obtained in the form of crystals (m.p. 55-57°C).; Example P3: Preparation of 3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester:A mixture of 2.08 g of S-trifluoromethyMH-pyrazole^-carboxylic acid ethyl ester (10 mmol) and 2.3 ml of trimethyl phosphate (20 mmol) is stirred at a temperature of 180°C for16 hours. 200 ml of an ice-water mixture are then added. The resulting reaction product is filtered, washed with water and dissolved in 50 ml of ethyl acetate. The organic phase is washed twice with 50 ml of saturated sodium chloride solution each time and dried over sodium sulfate and concentrated by evaporation. 1.9 g (86 percent of theory) of 3-trifluoromethyl-1 -methyl- 1 H-pyrazole-4-carboxylic acid ethyl ester are obtained in the form of crystals(m.p. 55-57°C).
Reference: [1] Patent: WO2006/45504, 2006, A1, . Location in patent: Page/Page column 5
  • 4
  • [ 155377-19-8 ]
  • [ 113100-53-1 ]
Reference: [1] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
[2] Molecules, 2015, vol. 20, # 3, p. 4383 - 4394
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4569 - 4574[4] Angew. Chem., 2017, vol. 129, # 16, p. 4640 - 4645,6
  • 5
  • [ 571-55-1 ]
  • [ 155377-19-8 ]
YieldReaction ConditionsOperation in experiment
95% With hydrazine hydrate In ethanol at 0 - 20℃; for 4.5 h; Hydrazine hydrate (10 g, 0.199 mol) was dissolved in ethanol (400 mL). This was cooled to 0 °C and a solution of ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate (47.03 g, 0.19 mol) in ethanol (200 mL) was added drop-wise over 90 min at 0 °C. The solution was left to warm to room temperature for 3 h and concentrated to dryness. The residue was dispersed in boiling cyclohexane (200 mL) and left to cool to room temperature. The precipitate was filtered, washed with cyclohexane and dried under vacuum at 75 °C to yield compound 3f as a yellow powder (38.67 g, 95percent); mp 145 °C 1H NMR (CDCl3): 1.40 (t, 3H, J=7.0 Hz); 4.39 (q, 2H, J=7.0 Hz); 8.26 (s, 1H); 13.2 (s (br), 1H). 13C NMR (CDCl3): 14.0; 61.2; 113.4; 121.0 (q, J=268 Hz); 135.3; 142.0 (q, J=38 Hz); 160.8. HRMS: calcd For C7H7F3N2O2-H: 207.0381; Found: 207.0377.
88% With hydrazine hydrate In ethanol at 0 - 20℃; for 24 h; Step 1 : A solution of hydrazine hydrate (34.4 g, 0.687 mol, 1.1 eq) in ethanol (400 mL) was added to a solution of compound 1 (150 g, 0.62 mol) in ethanol (1000 mL) at 0 °C. The reaction was allowed to warm to room temperature and stirred for 24 hr. The reaction was concentrated in vacuo, dissolved in ethyl acetate (2000 mL), washed with 5percent citric acid (2000 mL), sa d NaHCOs (2000 mL) and brine, dried (MgSC^), and concentrated in vacuo to afford a light yellow solid, compound 2 (113 g, 88percent).
88% With hydrazine In ethanol at 0 - 20℃; for 15 h; [00521] To a stirred solution of 1 (23.5 g, 98 mmol) in EtOH (150 mL), was added hydrazine (3.8 g, 117 mmol) dropwise at 0 oC. The reaction mixture was allowed to warm to room temperature and stirred for 15 h. The mixture was concentrated and the residue was dissolved in EtOAc (200 mL). The solution was washed with water, 0.5N HCl, saturated NaHCO3, and brine. The organic phase was dried over Na2SO4 and concentrated to dryness to afford crude compound 2 (18 g, 88percent) as a yellow solid, which was used without further purification.1H NMR (400 MHz, CD3OD): δ 8.31 (1H, d, J = 0.8 Hz), 4.29 (2H, q, J = 7.2 Hz), 1.34 (3H, J = 7.2 Hz).
88% With hydrazine hydrate In ethanol at 0 - 20℃; for 24 h; A solution of hydrazine hydrate (34.4 g, 0.687 mol, 1.1 eq) in ethanol (400 mL) was added to a solution of compound 1 (150 g, 0.62 mol) in ethanol (1000 mL) at 0 °C. The reaction was allowed to warm to room temperature and stirred for 24 hr. The reaction was concentrated in vacuo, dissolved in ethyl acetate (2000 mL), washed with 5percent citric acid (2000 mL), saf d NaHC03(2000 mL) and brine, dried (MgS04), and concentrated in vacuo to afford a light yellow solid, compound 2 (113 g, 88percent).

Reference: [1] Tetrahedron, 2011, vol. 67, # 44, p. 8451 - 8457
[2] Patent: WO2016/81918, 2016, A1, . Location in patent: Paragraph 00279
[3] Patent: WO2016/151403, 2016, A1, . Location in patent: Paragraph 00521
[4] Patent: WO2017/205684, 2017, A1, . Location in patent: Paragraph 00692; 00693
[5] Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 47 - 56
[6] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
[7] Molecules, 2015, vol. 20, # 3, p. 4383 - 4394
  • 6
  • [ 371-67-5 ]
  • [ 5941-50-4 ]
  • [ 155377-19-8 ]
YieldReaction ConditionsOperation in experiment
72% With sodium phosphate; silver(l) oxide In tetrahydrofuran at 20℃; for 3 h; Schlenk technique; Inert atmosphere In a dried reaction flask was weighed into 100mLSchlenk Ag 2 O (0.17g, 0.75mmol), Na 3 PO 4 (0.12g, 0.75mmol), 3- nitro-ethyl acrylate (0.73g, 0.5mmol), argon replacement three times, the System CF 3 CHN THF was added a solution of 2 (0.2M, 25mL), stirred at room temperature 3h. TLC monitoring Measuring the reaction is complete, the system was removed by filtration and the metal salts, residue was washed with ethyl acetate, the organic phase Combined, the solvent was evaporated under reduced pressure, the residue was dissolved in dichloromethane, washed with saturated ammonium chloride solution, dried over anhydrous sulfur Sodium sulfate, and column chromatography (eluent: petroleum ether / ethyl acetate = 10 / 1-5 / 1) to give the desired product 3- Trifluoromethyl -1H- pyrazole-4-carboxylic acid ethyl ester 0.65 g, 72percent yield, high performance liquid chromatography (HPLC) Purity of 99percent.
Reference: [1] Patent: CN105461629, 2016, A, . Location in patent: Paragraph 0038-0040
  • 7
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Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2785 - 2795
[2] Patent: EP1845081, 2007, A1,
  • 8
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  • [ 155377-19-8 ]
Reference: [1] Patent: WO2006/82952, 2006, A1, . Location in patent: Page/Page column 174-175
[2] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
[3] Molecules, 2015, vol. 20, # 3, p. 4383 - 4394
[4] Patent: WO2016/151403, 2016, A1,
  • 9
  • [ 371-67-5 ]
  • [ 5941-50-4 ]
  • [ 155377-19-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4569 - 4574[2] Angew. Chem., 2017, vol. 129, # 16, p. 4640 - 4645,6
  • 10
  • [ 16205-84-8 ]
  • [ 155377-19-8 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 44, p. 6566 - 6574
  • 11
  • [ 591-50-4 ]
  • [ 155377-19-8 ]
  • [ 741717-63-5 ]
YieldReaction ConditionsOperation in experiment
85% With trans-N,N'-dimethyl-1,2-cyclohexanediamine; copper(l) iodide; potassium carbonate In toluene at 110℃; for 24 h; A mixture of 3-trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (2.5 g, 12.0 mmol), copper (I) iodide (0.69 g, 3.6 mmol) and potassium carbonate (3.49 g, 25.3 mmol) in toluene (12 mL) in a round bottom flask was purged with argon. To the reaction mixture was then added iodobenzene (1.61 mL, 14.4 mmol) and racemic trans- N,N'-dimethyl-cyclohexane-l,2-diamine (1.16 mL, 7.2 mmol). The slurry was heated under Ar in an oil bath at HO0C for 24 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered over a bed of celite. The organic washings were combined and concentrated to give a crude which was purified by silica gel chromatography (Isco 120 g column, 0 -> 30percent ethyl acetate/hexanes) to give 1- phenyl-3-trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (2.91 g, 85percent) as an off-white solid. The NMR spectrum obtained on the sample is compatible with its structure.
85% With potassium carbonate In toluene at 110℃; for 24 h; Inert atmosphere Part I:
Preparation of Preferred Intermediates
Preparation of 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid
A mixture of 3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.5 g, 12.0 mmol), copper (I) iodide (0.69 g, 3.6 mmol) and potassium carbonate (3.49 g, 25.3 mmol) in toluene (12 mL) in a round bottom flask was purged with argon.
To the reaction mixture was then added iodobenzene (1.61 mL, 14.4 mmol) and racemic trans-N,N'-dimethyl-cyclohexane-1,2-diamine (1.16 mL, 7.2 mmol).
The slurry was heated under Ar in an oil bath at 110° C. for 24 hours.
After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered over a bed of celite.
The organic washings were combined and concentrated to give a crude which was purified by silica gel chromatography (Isco 120 g column, 0-->30percent ethyl acetate/hexanes) to give 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.91 g, 85percent) as an off-white solid.
The NMR spectrum obtained on the sample is compatible with its structure.
A mixture of 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.25 g, 4.4 mmol) and 1N aqueous sodium hydroxide solution (17.3 mL) in methanol (20 mL) was stirred at room temperature overnight.
The reaction mixture was concentrated and acidified to pH~1 with 1N aqueous hydrochloric acid.
The slurry was extracted with methylene chloride and the combined organic layers were washed with saturated sodium chloride and dried over sodium sulfate.
Filtration and concentration gave 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (1 g, 89percent yield) as an off-white solid, which was directly used in the next step without further purification. LCMS calcd for C11H7F3N2O2 (m/e) 256, obsd 255 (M-H).
77% With potassium carbonate In toluene at 110℃; for 24 h; Sealed tube According to the procedure of Buchwald et al . (J. Oxg. Chem. 2004, 69, 5578), to a 350 iaL sealed tube flushed vigorously with nitrogen was added ethyl 3- (trifluoromethyl) - lH-pyrazole-4-carboxylate (20.0 g, 96.1 mmol) , 1-iodobenzene (12.9 inL, 115 mmol), potassium carbonate (27.9 g, 202 mmol), copper(I) iodide (0.915 g, 4.80 mmol), and (IS, 2S) -N1,N2- dimethylcyclohexane-l,2-diamine (1.37 g, 9.61 mmol), followed by degassed (argon) toluene (100 mL) . The mixture was stirred for 24 hours at 1100C, cooled to room temperature, and filtered through a short silica pad which was thoroughly rinsed with toluene and AcOEt- The filtrate was concentrated in vacuo to give ethyl l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (21 g, 77percent) as a solid: 1H NMR (400 MHz, CDCl3) δ 1.39 (t, 3H, J = 7.0 Hz), 4.37 (q, 2H, J = 7.0 Hz), 7.42 (m, IH), 7.52 (m, 2H), 7.72 (m, 2H), 8.48 (m, IH).
77% With potassium carbonate In toluene at 110℃; for 24 h; sealed tube According to the procedure of Buchwald et al. [J. Org. Chem. 2004, 6"S, 5578), to a 350 mL sealed tube flushed vigorously with nitrogen were added ethyl 3- (trifluoromethyl) - lH-pyrazole-4-carboxylate (20.0 g, 96.1 ramol) , 1-iodobenzene s (12.9 ml, 115 mmol) , potassium carbonate (27.9 g, 202 mmol), copper (I) iodide (0.915 g, 4.80 mmol), and (IS, 2S) -N1,N2- dimethylcyclohexane-l,2-diamine (1.37 g, 9.61 mmol), followed by degassed toluene (100 ml) . The mixture was stirred for 24 hours a.t 1100C7 cooled to room temperature, and filtered through o a short silica pad which was rinsed with toluene and EtOAc thoroughly. The filtrate was concentrated in vacuo to give ethyl l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxylate(21 g, 77percent) as a solid: 1H NMR (400 MHz, CDCl3) δ 1.39 (t, 3H, J = 7.0 Hz), 4.37 (q, 2H, J = 7.0 Hz), 7.42 (m, IH), 7.52 (m, 2H), 5 7.72 (m, 2H), 8.48 (m, IH).

Reference: [1] Patent: WO2008/141976, 2008, A1, . Location in patent: Page/Page column 55
[2] Patent: US2010/152445, 2010, A1, . Location in patent: Page/Page column 8
[3] Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5578 - 5587
[4] Patent: WO2008/11130, 2008, A2, . Location in patent: Page/Page column 134-135
[5] Patent: WO2008/11131, 2008, A2, . Location in patent: Page/Page column 270-271
[6] Patent: WO2006/13939, 2006, A1, . Location in patent: Page/Page column 47-48
[7] Patent: US2007/123504, 2007, A1, . Location in patent: Page/Page column 29
  • 12
  • [ 98-80-6 ]
  • [ 155377-19-8 ]
  • [ 741717-63-5 ]
Reference: [1] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2785 - 2795
  • 13
  • [ 155377-19-8 ]
  • [ 591-50-4 ]
  • [ 741717-63-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2527 - 2531
  • 14
  • [ 155377-19-8 ]
  • [ 543739-84-0 ]
Reference: [1] Patent: WO2004/54974, 2004, A2, . Location in patent: Page 452
[2] Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 47 - 56
[3] Patent: WO2009/12482, 2009, A2, . Location in patent: Page/Page column 76
  • 15
  • [ 155377-19-8 ]
  • [ 1001020-13-8 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 10 - 20℃; for 4.5 h; Cooling with acetone/ice bath
Stage #2: at 20℃;
Ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (95.00 g, 0.456 mol) was dissolved in dry THF (1 L) and the resulting solution cooled in an acetone/ice bath. A 1M solution of LiAlH4 in THF (550 mL, 0.550 mol) was added over 30 min, keeping the temperature <10° C. Cooling was then removed and the reaction mixture was stirred at RT for 4 h. The reaction was again cooled and a 1:1 THF:water solution (250 mL) was added with cooling (maintaining the temperature <20° C.), followed by 5M HCl (160 mL) to neutrality/pH 6. EtOAc (1.5 L) was added and the mixture stirred for 30 min then left to settle overnight. The resulting grey granular solid was removed by filtration through dicalite and washed with EtOAc. The combined filtrates were washed with brine and dried over MgSO4, before concentrating in vacuo to give a white solid (76.00 g, 0.457 mol, 100percent).1H NMR (400 MHz, CD3OD): δ 4.61 (s, 2H), 7.75 (s, 1H).
53%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3 h;
Stage #2: With methanol In tetrahydrofuran for 0.5 h;
Example 54; 2-(2-(4-(dimethylamino)methyl)-3-(trifluoromethyl)pyrazol-1-yl)acetamido)-4, 5,6,7- tetrahydrobenzof/?1thiophene-3-carboxamidea) (3-(trifluoromethyl)-7H-pyrazol-4-yl)methanolEthyl 3-(trifluoromethyl)-1 H-pyrazole-4-carboxylate (5.00 g, 24 mmol) was dissolved in dry THF (5OmL). LiAIH4 (912 mg, 24.4 mmol) was added portionwise with care. The reaction mixture was stirred at RT for 3 h. MeOH (50 mL) was added dropwise and stirring continued for 30 min before concentrating in vacuo to give an off white solid. EtOAc (50 mL) was added and the solid was stirred for 30 min before filtering. The filtrate was concentrated and this procedure was repeated 4 times before the filtrates, after concentration in vacuo, were combined and purified by flash column chromatography <n="54"/>(silica gel; eluent EtOAc: heptane, 4:1) to give the desired product (2.1 g, 12.6 mmol, 53percent).1 H NMR (400MHz, CD3OD): δ 4.65 (s, 2H), 7.63 (s, 1 H)
50.1% With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃; for 4.5 h; Ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (1.50 g, 7.21 mmol) was dissolved in dry THF (50 mL) and the resulting solution cooled to -78 oC. To the resulting solution was added, 2 M solution of LAH (6.01 mL, 14.41 mmol) in THF over 30 min by keeping the temperature <10 °C. The reaction mixture was allowed to come to ambient temperature, stirred for 4 h and was cooled again with to -10 oC. The reaction was quenched with the addition of 1:1 THF:water (50 mL) mixture with cooling (maintaining the temperature <20 °C), followed by 5M HCl to neutralise to pH 6. The reaction mixture was diluted with EtOAc (100 mL), stirred for 30 min and left to settle for 1 h. The resulting solid was removed by filtration through Celite® and washed with EtOAc. The filtered organic layer was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was triturated with ether (2 x 25 mL) to obtain Intermediate 89A (0.60 g, 50.10percent).1H NMR (400 MHz, DMSO-d6) δ ppm 4.44 (s, 2 H), 5.02 (s, 1 H), 7.83 (s, 1 H), 13.73 (br. s., 1 H). LCMS (Method-H): retention time 0.54 min, [M- H] 165.0.
Reference: [1] Patent: US2009/131455, 2009, A1, . Location in patent: Page/Page column 7-8
[2] Patent: WO2008/3452, 2008, A1, . Location in patent: Page/Page column 52-53
[3] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 173; 174
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