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[ CAS No. 1174013-25-2 ] {[proInfo.proName]}

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Chemical Structure| 1174013-25-2
Chemical Structure| 1174013-25-2
Structure of 1174013-25-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1174013-25-2 ]

CAS No. :1174013-25-2 MDL No. :MFCD28134168
Formula : C10H15F3O5S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 304.28 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1174013-25-2 ]

* 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.

  • Downstream synthetic route of [ 1174013-25-2 ]

[ 1174013-25-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1174013-25-2 ]
  • [ 50650-59-4 ]
  • [ 1207447-22-0 ]
YieldReaction ConditionsOperation in experiment
Intermediate: (S)-methyl 3-cyclopentyl-2-(2-oxo-4-(thfluoromethyl)pyridin-1 (2H)- yl)propanoate (1d)(1d)To a stirred solution of 4-(trifluoromethyl)pyridin-2(1 /-/)-one (946 mg, 5.8 mmol) in anhydrous THF (40 ml_) at room temperature under nitrogen, was added a solution of lithium bis(trimethylsilyl)amide (5.2 ml_, 5.2 mmol, 1.0M in THF). After stirring for 40 minutes, a solution of (f?)-methyl 3-cyclopentyl-2-(trifluoromethylsulfonyloxy)propanoate (1c) (1.77 g, 5.81 mmol) in anhydrous THF (10 ml_) was added. The reaction was then stirred for 1.5 hours and quenched with aqueous saturated ammonium chloride and diluted with brine and ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organics were dried over sodium sulfate, filtered, and evaporated. The residue was purified (Combi-flash, Redi-sep 8Og, 25% ethyl acetate/heptane gradient to 80% ethyl acetate/heptane, 254nm detection, 240nm monitoring, all fractions collected, the product has weak uv). The product fractions were combined, evaporated, and dried under reduced pressure to provide (S)-methyl 3- cyclopentyl-2-(2-oxo-4-(trifluoromethyl)pyhdin-1 (2H)-yl)propanoate (1 d) (1.33g). 1 H NMR (400 MHz, CDCI3) delta 7.46-7.45 (1 H), 6.81 (1 H), 6.33-6.31 (1 H), 5.60-5.56 (1 H), 3.72 (3 H), 2.12-2.09 (1 H), 2.03-1.99 (1 H), 1.79-1.46 (7 H), 1.23-1.05 (2 H); LCMS for Ci5Hi8F3NO3 m/z 318.1 (M+H)+.
  • 2
  • [ 1603-41-4 ]
  • [ 864239-61-2 ]
  • [ 1174013-25-2 ]
  • [ 1215197-92-4 ]
  • [ 1215197-93-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methyl-4-(trifluoromethyl)-1H-pyrazole With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.833333h; Inert atmosphere; Stage #2: (R)-methyl 3-cyclopentyl-2-(((trifluoromethyl)sulfonyl)oxy)-propanoate In tetrahydrofuran at 20℃; for 3h; Stage #3: (5-methyl-pyridin-2-yl)amine With trimethylaluminum In 1,2-dimethoxyethane; hexane Reflux; 96 To a solution of 5-methylpyridin-2-amine (63.6 mg, 0.59 mmol) in 1.4 ml_ of dimethoxyethane was added dimethylaluminum chloride (1.0M in hexanes, 1.2 ml_, 1.2 mmol). After stirring for 1 hour at O0C, it was poured into a solution of intermediates (I- 20b) and (l-20c) (89.4 mg, 0.29 mmol, combined) in 1.5ml_ of dimethoxyethane. The mixture was heated at reflux for 3 h before cooling and concentrating. The residue was taken up in dichloromethane and stirred with saturated aqueous Rochelle's salts for 1 hour. The layers were separated and the aqueous layer was reextracted with dichloromethane twice. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography (ISCO 12g, 30-60% ethyl acetate/heptane) to afford Example 96 and Example 97. 1H NMR (400 MHz, CDCI3) δ 9.18 (1 H), 8.10 - 8.14 (1 H), 8.02 (1 H), 7.73 (1 H), 7.49 (1 H), 4.73 - 4.82 (1 H), 2.40 (3 H), 2.27 (3 H), 2.24 - 2.27 (1 H), 2.13 - 2.22 (1 H), 1.37 1.81 (5 H), 1.01 - 1.29 (4 H); m/z 381.0 (M+H)+.Example 97: (S)-3-cyclopentyl-2-(5-methyl-4-(trifluoromethyl)-1 H-pyrazol-1 -yl)-Λ/-(5- methylpyridin-2-yl)propanamide of Formula (1A-16).(1A-16)Prepared by the reaction described above for Example 96 to provide the title compound. 1H NMR (400 MHz, CDCI3) δ 9.24 (1 H), 8.08 (1 H), 8.01 (1 H), 7.84 (1 H), 7.48 (1 H), 4.80 (1 H), 2.42 - 2.51 (1 H), 2.41 (3 H), 2.26 (3 H), 2.14 - 2.24 (1 H), 1.42 - 1.76 (5 H), 0.97 - 1.32 (4 H); m/z 380.9 (M+H)+.
  • 3
  • [ 864239-61-2 ]
  • [ 1174013-25-2 ]
  • [ 1215198-31-4 ]
  • [ 1215198-30-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methyl-4-(trifluoromethyl)-1H-pyrazole With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.833333h; Inert atmosphere; Stage #2: (R)-methyl 3-cyclopentyl-2-(((trifluoromethyl)sulfonyl)oxy)-propanoate In tetrahydrofuran at 20℃; for 3h; Intermediate (l-20a) (150.1 mg, 1.00 mmol) was stirred in 5 ml_ of dry THF at room temperature under nitrogen. Lithium hexamethyldisilazide solution (1.0M in THF, 0.91 ml_, 0.909 mmol) was added dropwise. After 50 minutes, a solution of intermediate (1-1 c) (304 mg, 1.00 mmol) in 1 ml_ of dry THF was added. The reaction was stirred for 3 hours. The reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate three times. The combined organic layer was concentrated and purified by silica gel chromatography (ISCO 12g, ethyl acetate/heptane 30-100%) to afford a mixture of (l-20b) and (l-20c) as a yellow oil (153 mg); m/z 304.9 (M+H)+.
  • 4
  • [ 1174013-25-2 ]
  • [ 33468-69-8 ]
  • [ 1215198-05-2 ]
YieldReaction ConditionsOperation in experiment
67% 4-Tiotafluoromethyl-1 /-/-imidazole (5.0 g, 37.0 mmol; Apollo Scientific Ltd., Bredbury, Cheshire, UK) was stirred in dry THF (180 ml_) under nitrogen at room temperature. Lithium hexamethyldisilazide (1 M in THF, 33.4 mL, 33.4 mmol) was added dropwise via addition funnel. The mixture was stirred at room temperature for 50 minutes and then chilled in an ice bath. A solution of (1-1 c) (11.3 g, 37 mmol) in dry THF (45 mL), which had been chilled in an ice bath, was added in one portion. The reaction was allowed to warm to room temperature, stirred for 2 hours, quenched with saturated aqueous ammonium chloride solution (20 mL) and allowed to stir overnight. The aqueous layer was separated, and the organic layer was concentrated and then diluted with water and ethyl acetate. The organic layer was washed in series with dilute aqueous phosphoric acid, aqueous 10% potassium carbonate, and brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated under reduced pressure to a brown oil. The crude material, containing the undesired regioisomer as a small impurity, was purified by chromatography on a 330 g pre-packed silica gel column, eluting with 10% ethyl acetate/heptane, linear gradient to 70% ethyl acetate/heptane. The product fractions were located by spotting on a silica TLC plate and visualizing with KMnO4 stain. TLC (1 :1 ethyl acetate/heptane, developed in potassium permanganate) located the pure and mixed fractions. The clean product fractions were combined, evaporated, and dried under high vacuum to afford (l-8a) as a clear oil (6.61 g, 22.4 mmol, 67%). 1H NMR (400 MHz, CDCI3) delta 7.57 (1 H), 7.38 (1 H), 4.71 - 4.74 (1 H), 3.76 (3 H), 2.01 - 2.14 (2 H), 1.45 - 1.79 (7 H), 1.03 - 1.18 (2 H); m/z 291.4 (M+H)+.
  • 5
  • [ 1174013-25-2 ]
  • [ 33468-67-6 ]
  • [ 1215198-25-6 ]
YieldReaction ConditionsOperation in experiment
47% To a stirred solution of 2-methyl-4-(trifluoromethyl)-1 /-/-imidazole (Chireach USA LLC, San Diego, CA) (197 mg, 1.3 mmol) in anhydrous THF (8 mL) under N2 was added a solution of lithium hexamethyldisilazide (1.24 mL, 1 M in hexanes, 1.24 mmol). After stirring for 45 minutes at room temperature, a solution of Intermediate (1-1 c) (400 mg, 1.32 mmol) in 8 mL of anhydrous THF was added dropwise and stirring was continued for 4 hours at room temperature. It was then quenched with aqueous saturated NH4CI and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (SiO2, heptane / ethyl acetate, O to 50%) to afford (1-17a) in 47% yield; m/z 305.4 (IvRH)+.
  • 6
  • [ 1174013-25-2 ]
  • [ 1215197-94-6 ]
  • [ 1215197-95-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(isopropylthio)-1H-pyrazole With lithium hexamethyldisilazane In tetrahydrofuran; hexane for 0.75h; Inert atmosphere; Stage #2: (R)-methyl 3-cyclopentyl-2-(((trifluoromethyl)sulfonyl)oxy)-propanoate In tetrahydrofuran; hexane at 20℃; for 2h; To a stirred solution of 124 mg of (l-2a) in 9 ml_ of anhydrous THF under nitrogen, a solution of lithium bis(trimethylsilyl)amide (0.784 ml_, 1 M in hexanes) was added. After 45 minutes, a solution of Intermediate (1-1 c) (265 mg in 6 ml_ of anhydrous THF) was added dropwise and stirring continued for 2 hours at room temperature. It was then quenched with aqueous saturated NH4CI and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (silca gel, 0-100% ethyl acetate in heptane) to afford (l-3a), m/z 297.1 (M+H)+
  • 7
  • [ 21744-55-8 ]
  • [ 1174013-25-2 ]
  • [ 1215198-11-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methanesulfonyl-1<i>H</i>-tetrazole With lithium hexamethyldisilazane In tetrahydrofuran for 0.666667h; Inert atmosphere; Stage #2: (R)-methyl 3-cyclopentyl-2-(((trifluoromethyl)sulfonyl)oxy)-propanoate In tetrahydrofuran for 2h; To a stirred solution of 200 mg of (1-11 a) in anhydrous THF (10 ml_) under nitrogen was added lithium bis(trimethylsilyl)amide (0.276 ml_, 1 M in THF). After stirring for 40 minutes, a solution of Intermediate (1-1 c) (414 mg) in anhydrous THF (2 ml_) was added dropwise. After 2 hours, the reaction was quenched with aqueous saturated NH4CI and extracted with ethyl acetate twice. The combined organics were dried over MgSO4 and purified by flash chromatography (10g snap Biotage, 0-10% methanol in dichloromethane) to give 0.18O g of (1-11 b) as an oil; m/z 303.1 (M+H)+.
  • 8
  • [ 1174013-25-2 ]
  • [ 1254730-41-0 ]
  • [ 1254730-43-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methylsulfonyl-2-pyridone With lithium hexamethyldisilazane In tetrahydrofuran at 23℃; for 0.75h; Stage #2: (R)-methyl 3-cyclopentyl-2-(((trifluoromethyl)sulfonyl)oxy)-propanoate In tetrahydrofuran at 23℃; for 2h;
  • 9
  • [ 36953-37-4 ]
  • [ 1174013-25-2 ]
  • [ 1254730-45-4 ]
  • 10
  • [ 1174013-25-2 ]
  • [ 18085-51-3 ]
  • [ 1254730-44-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methanesulfonyl-1H-pyridin-2-one With lithium hexamethyldisilazane In tetrahydrofuran at 23℃; for 0.75h; Stage #2: (R)-methyl 3-cyclopentyl-2-(((trifluoromethyl)sulfonyl)oxy)-propanoate In tetrahydrofuran at 23℃; for 2h;
  • 11
  • [ 1174013-25-2 ]
  • [ 33468-69-8 ]
  • [ 1215198-05-2 ]
  • (R)-methyl 3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanoate [ No CAS ]
  • [ 1401513-86-7 ]
  • 12
  • [ 1174013-25-2 ]
  • [ 33468-69-8 ]
  • [ 1215198-05-2 ]
  • [ 1401513-86-7 ]
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