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[ CAS No. 164341-39-3 ] {[proInfo.proName]}

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Chemical Structure| 164341-39-3
Chemical Structure| 164341-39-3
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Product Citations

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Giri R. Gnawali ; Koichi Okumura ; Karolina Perez , et al. DOI: PubMed ID:

Abstract: Compound VBT-5445 was identified as an inhibitor to block the association of Pim and the protein Enhancer of Decapping 3 (EDC3), a Pim substrate, which normally functions to enhance the decapping of messenger RNA (mRNA). It was also shown to inhibit both the Pim and mTORC protein kinases. The activity of this compound class can be fine-tuned by structural modification. A series of VBT analogs were designed, synthesized, and evaluated. These compounds decrease the growth of multiple cancer types, including pancreas, prostate, breast, lung, and leukemia. Notably, 6-methyl (GRG-1-31, 6d), 4-chloro (GRG-1-34, 6e), 4-Bromo (GRG-1-35, 6f), and phenylthio substituted (GRG-1-104, 6n) derivatives are highly potent at inhibiting tumor growth. The ability of these compounds to block cancer growth in vitro is highly correlated with their activity as mTORC inhibitors. The toxicity of GRG 1–34 is low in mice treated with twice-daily gavage for 30 days and did not induce weight loss. Pharmacokinetics of a single oral dose demonstrated a peak concentration at 0.5?h after gavage. In summary, further development of this compound class has the potential to inhibit important signaling pathways and impact cancer treatment.

Keywords: Quinoline derivatives ; Pim kinase ; Antitumor activity ; mTORC

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Product Details of [ 164341-39-3 ]

CAS No. :164341-39-3 MDL No. :MFCD04117761
Formula : C7H7F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :HVQOLQUEKRHKKJ-UHFFFAOYSA-N
M.W : 176.14 Pubchem ID :3796375
Synonyms :

Safety of [ 164341-39-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 164341-39-3 ]

* 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 [ 164341-39-3 ]

[ 164341-39-3 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 80194-70-3 ]
  • [ 175277-74-4 ]
  • [ 164341-39-3 ]
YieldReaction ConditionsOperation in experiment
97%; 0.05% With hydrogen; acetic acid;nickel; at 40 - 45℃; under 13501.4 Torr; for 4h; Example of the preparation of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine 400g of acetic acid and 6g of Ni-Ra (previously washed with water until washings were at a pH of 7) were loaded in a 1L stainless steel reactor. The reactor was purged with nitrogen and then hydrogen. Heating was applied to the reactor to raise the temperature up to 40C and the reactor pressure was raised to 18 bar with hydrogen. 120g of 3-chloro-2-cyano-5-trifluoromethylpyridine (0.571 mol) were added by pump over 2 hours. The reaction was exothermic and temperature raised to 45C. Hydrogen consumption was monitored. After 2 hours, no more hydrogen was consumed and the reaction was complete. The mixture was cooled down to 20C and then vented off and purged with nitrogen. The catalyst was filtered. The solution of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine acetic acid salt was assayed by liquid chromatography. 0.558 moles of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine was formed and a 97% yield of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine over 3-chloro-2-cyano-5-trifluoromethylpyridine was obtained. A yield of only 0.05% yield of the dechlorinated analogue was obtained.
YieldReaction ConditionsOperation in experiment
[5-(trifluoromethyl)-2-pyridinyl]methylamine The title compound was prepared using the procedure described in Example 172B using 5-(trifluoromethyl)-2-pyridinecarbonitrile instead of 4-(4-morpholinyl)benzonitrile.
  • 3
  • [ 164341-39-3 ]
  • [ 357286-73-8 ]
  • [ 357288-40-5 ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane; 2-Amino-4-furan-2-yl-6-[(5-trifluoromethyl-pyridin-2-yl-methyl)-amino]-pyrimidine-5-carbonitrile From 2-amino-4-furan-2-yl-6-methanesulfinyl-pyrimidine-5-carbonitrile and <strong>[164341-39-3]C-(5-trifluoromethyl-pyridin-2-yl)-methylamine</strong> in DME. ES-MS m/e (%): 361 (M+H+, 100).
  • 4
  • [ 95727-86-9 ]
  • [ 164341-39-3 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 301B [5-(trifluoromethyl)-2-pyridinyl]methylamine The title compound was prepared using the procedure described in Example 172B using 5-(trifluoromethyl)-2-pyridinecarbonitrile instead of 4-(4-morpholinyl)benzonitrile.
Example 301B [5-(trifluoromethyl)-2-pyridinyl]methylamine The title compound was prepared using the procedure described in Example 172B using 5-(trifluoromethyl)-2-pyridinecarbonitrile instead of 4-(4-morpholinyl)benzonitrile.
  • 5
  • [3-chloro-5-(trifluoromethyl)-pyridin-2-yl]methanamine hydrochloride [ No CAS ]
  • [ 164341-39-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; sodium hydrogencarbonate;palladium 10% on activated carbon; In methanol; for 3h; (5-(Trifluoromethyl)pyridin-2-yl)methanamine (VI) was prepared as follows: Sodium bicarbonate (0.25 g) and palladium on carbon (0.5 g, 50% wet, 10% Pd/C) were added to a methanolic solution of the hydrochloride chloride salt of (3-chloro-5-(trifluoro-methyl)pyridin-2-yl)methanamine (V) (0.5 g in 50 mL methanol). The mixture was hydrogenated under a hydrogen balloon over 3 h. The reaction mixture was filtered, and evaporated in vacuo. The residue was re-dissolved in methanol (5 mL), re-filtered, and re-evaporated to give crude product (VI) (0.33 g). 1H-NMR (CD3OD, 400 MHz): delta 8.92 (s, 1H), 8.16 (d, J=8.2 Hz, 1H), 7.66 (d, J=8.2 Hz, 1H), 4.35 (s, 2H).
  • 6
  • [ 321126-82-3 ]
  • [ 164341-39-3 ]
  • [ 32315-10-9 ]
  • [ 1338065-23-8 ]
YieldReaction ConditionsOperation in experiment
37% To a solution of triphosgene (0.07 g, 0.37 mol eq) in anh. CH2C12 (10 mL) was slowly added the amine If (0.2g, 1 mmol) solubilized in CH2C12 (10 mL) and DIEA (2.2 mol eq, 0.4 mL). After the addition was completed, the reaction mixture was stirred at room temp, for 15 min. Then the [5-(trifluoromethyl)-2- pyridyljmethanamine (1 mol eq, 0.18g) solubilized in CH2C12 (10 mL) and DIEA (2.2 mol eq, 0.4 mL) was added in one portion. The mixture obtained was stirred at room temp, for 12 h. The solvent was removed at reduced pressure, water was added and the mixture was extracted with EtOAc (3x20 mL). The recombined organic phases were anhydrified over sodium sulfate and evaporated to dryness. The residue was purified by crystallization from EtOAc to obtain the product as yellow solid (0.132g, 37% Yield). 1HNMR (DMSO, 400 MHz) delta 4.47 (d, 2H, J=6), 4.63 (s, 2H), 6.46 (dd, 1H, J=2), 6.80 (t, 1H, J=8), 7.57m, 2H), 7.72 (dd, 1H, J=2), 8.18 (dd, 1H, J=2), 8.22 (s, 1H), 8.90 (m, 1H), 10.66 (s, 1H). [M+1] 366.94 (C16H13F3N4O3 requires 366.29).
  • 7
  • [ 75370-65-9 ]
  • [ 164341-39-3 ]
  • [ 32315-10-9 ]
  • [ 1338064-79-1 ]
YieldReaction ConditionsOperation in experiment
16% To a solution of triphosgene (0.148 g, 0.37 mol eq) in anh. CH2C12 (10 mL) was slowly added the amine la (0.2g, 1.34 mmol) solubilized in CH2C12 (10 mL) and DIEA (2.2 mol eq, 0.5 mL). After the addition was completed, the reaction mixture was stirred at room temp, for 15 min. Then the [5- (trifluoromethyl)-2-pyridyl]methanamine (1 mol eq, 0.23g) solubilized in CH2C12 (10 mL) and DIEA (2.2 mol eq, 0.5 mL) was added in one portion. The mixture obtained was stirred at room temp, for 12 h. The solvent was removed at reduced pressure, water was added and the mixture was extracted with EtOAc (3x20 mL). The recombined organic phases were anhydrified over sodium sulfate and evaporated to dryness. The residue was purified by chromatography (9.5:0.5 EtoAc:MeOH) to obtain the product as yellow solid (0.075g, 0.22 mmol, 16% Yield). 'HNMR (DMSO, 400 MHz) delta 4.35 (d, 2H, J=6), 6.22 (t, 1H, J=4), 6.65 (d, 1H, J=6), 6.88 (m, 2H), 7.63 (d, 1H, J=8), 8.21 (dd, 1H), 8.48 (s, 1H), 8.91 (m, 1H), 9.99 (bs, 1H), 10.60 (bs, 1H). [M+1] 351.60 (C15H12F3N5O2 requires 351.28).
  • 8
  • [ 164341-39-3 ]
  • ethyl 6-(trifluoromethyl)imidazo[1,5-a]pyridine-3-carboxylate [ No CAS ]
  • 9
  • [ 164341-39-3 ]
  • [ 4755-77-5 ]
  • ethyl 2-oxo-2-[[5-(trifluoromethyl)-2-pyridyl]methylamino]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere; To a solution of <strong>[164341-39-3][5-(trifluoromethyl)-2-pyridyl]methanamine</strong> (1.0 g, 5.7 mmol) in anhydrous tetrahydrofuran cooled to 0 C under nitrogen was added triethylamine (1.19 mL, 8.5 mmol) followed by ethyl 2-chloro-2-oxo-acetate (0.85 g, 6.25 mmol). The reaction mixture warmed to RT slowly and stirred for 16 h. The reaction mixture was concentrated to dryness in vacuo and partitioned between isopropyl acetate (100 mL) and saturated aqueous sodium bicarbonate (50 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate, and concentrated to dryness in vacuo affording ethyl 2-oxo-2-[[5-(trifluoromethyl)-2-pyridyl]methylamino]acetate (1.2 g, 77%) as an orange solid used in the next step without further purification: LCMS RT = 1.05 min, m/z = 277 [M + H]+.
  • 10
  • [ 164341-39-3 ]
  • [ 98141-42-5 ]
  • C13H10ClF3N6 [ No CAS ]
  • 11
  • [ 164341-39-3 ]
  • 4-[2-(4-chloro-3-fluorophenoxy)acetamido]-2-oxobicyclo[2. 2. 2]octane-1-carboxylic acid [ No CAS ]
  • 4-[2-(4-chloro-3-fluorophenoxy)acetamido]-2-hydroxy-N-[5-(trifluoromethyl)pyridin-2-yl]methyl}bicyclo[2.2.2]octane-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46 mg A mixture of Example 7G (50 mg, 0.135 mmol), (5-(trifluoromethyl)pyridin-2- yl)methanamine (29.8 mg, 0.169 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.059 mL, 0.338 mmol) in N,N-dimethylformamide (1.5 mL) was treated with 2-(3H-[1,2,3jtriazolo[4,5-bjpyridin-3 -yl)- 1,1,3 ,3-tetramethylisouronium hexafluorophosphate(V) (77 mg, 0.203 mmol), and the reaction was stirred at ambient temperature for 16 hours. The mixture was concentrated, and the residue was dissolved in dichloromethane/methanol (1:1 mixture, 2 mL) and treated with sodium borohydride (25.6 mg, 0.676 mmol). The mixture was stirred atambient temperature for 1 hour. The mixture was concentrated under vacuum, and the cmde residue was purified by HPLC (performed on a Phenomenex Luna C 18(2) 5 tm boAAXIATM column (250 mm x 21.2 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) is used, at a flow rate of 25 mL/minute. A linear gradient is used from about5% of A to about 95% of A over about 10 minutes. Detection method is UV at wave length of218 nM and 254 nM) to give 46 mg of product as a white solid. ?H NMR (400 MHz, DMSOd 6) 5 ppm 8.82 (d, J = 2.2 Hz, 1H), 8.17 (t, J = 5.9 Hz, 1H), 8.09 (dd, J = 8.4, 2.4 Hz, 1H), 7.53-7.40 (m, 3H), 6.99 (dd, J = 11.4, 2.8 Hz, 1H), 6.78 (dd, J = 8.9, 2.8 Hz, 1H), 4.40 (d, J = 6.0Hz, 4H), 4.07 (dd, J = 9.4, 2.7 Hz, 1H), 2.23 (ddd, J = 12.6, 9.2, 2.8 Hz, 1H), 2.11 (td, J = 11.9,3.7 Hz, 1H), 1.86 (if, J = 15.4, 7.8 Hz, 1H), 1.78-1.54 (m, 7H); MS (ESI?)m/z 530.2 (M+H).
  • 12
  • [ 164341-39-3 ]
  • 3-[[2-(4-chloro-3-fluorophenoxy)acetyl]amino]bicyclo[1.1.1]pentane-1-carboxylic acid [ No CAS ]
  • 3-[2-(4-chloro-3-fluorophenoxy)acetamido]-N-[5-(trifluoromethyl)pyridin-2-yl]methyl}bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; for 16h; A mixture of the product of Example 18A (70 mg, 0.223 mmol), <strong>[164341-39-3](5-(trifluoromethyl)pyridin-2-yl)methanamine</strong> (47.2 mg, 0.27 mmol), N-[(dimethylamino)-1H-1 ,2,3-triazolo- [4,5 -bj pyridin- 1 -ylmethylenel -N-methylmethanaminium hexafluorophosphate Noxide (HATU, 102 mg, 0.27 mmol), and triethylamine (0.062 mL, 0.45 mmol) in tetrahydrofuran (3 mL) was stirred for 16 hours. The reaction mixture was treated with water and brine and extracted with ethyl acetate. The combined organic layers were concentratedunder reduced pressure, and the residue was purified by reverse-phase HPLC performed on a Phenomenex Zorbax Rx-C18 column (250 x 21.2 mm, 7 im particle size) using a gradient of 10% to 95% acetonitrile/0.1% aqueous trifluoroacetic acid over 30 minutes at a flow rate of 18 mL/minute to provide the title compound (38.0 mg, 0.08 1 mmol, 36% yield). ?H NMR (501MHz, DMSO-d6) 5 ppm 8.89 (dt, J = 1.9, 1.0 Hz, 1H), 8.73 (s, 1H), 8.52 (t, J = 6.0 Hz, 1H),8.23-8.11 (m, 1H), 7.57-7.39 (m, 2H), 7.08 (dd, J = 11.4, 2.9 Hz, 1H), 6.86 (ddd, J = 9.0,2.9, 1.2 Hz, 1H), 4.48 (s, 2H), 4.43 (d, J = 6.0 Hz, 2H), 2.24 (s, 6H); MS (ESI) m/z 472.1 (M+H).
36% With triethylamine; HATU; In tetrahydrofuran; for 16h; A mixture of the product of Example 18A (70 mg, 0.223 mmol), (5- (0883) (trifluoromethyl)pyridin-2-yl)methanamine (47.2 mg, 0.27 mmol), N-[(dimethylamino)-lH- l,2,3-triazolo-[4,5-]pyridin-l-ylmethylene]-N-methylmethanaminium hexafluorophosphate N- oxide (HATU, 102 mg, 0.27 mmol), and triethylamine (0.062 mL, 0.45 mmol) in tetrahydrofuran (3 mL) was stirred for 16 hours. The reaction mixture was treated with water and brine and extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure, and the residue was purified by reverse -phase HPLC performed on a Phenomenex Zorbax Rx-C18 column (250 x 21.2 mm, 7 mupiiota particle size) using a gradient of 10% to 95% acetonitrile/0.1% aqueous trifluoroacetic acid over 30 minutes at a flow rate of 18 mL/minute to provide the title compound (38.0 mg, 0.081 mmol, 36% yield). JH NMR (501 MHz, DMSO-<) <5 ppm 8.89 (dt, J = 1.9, 1.0 Hz, 1H), 8.73 (s, 1H), 8.52 (t, J = 6.0 Hz, 1H), 8.23 - 8.11 (m, 1H), 7.57 - 7.39 (m, 2H), 7.08 (dd, J = 11.4, 2.9 Hz, 1H), 6.86 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.48 (s, 2H), 4.43 (d, J = 6.0 Hz, 2H), 2.24 (s, 6H); MS (ESI+) m/z 472.1 (M+H)+.
  • 13
  • [ 164341-39-3 ]
  • 3-[[2-(4-chloro-3-fluorophenoxy)acetyl]amino]bicyclo[1.1.1]pentane-1-carboxylic acid [ No CAS ]
  • 3-[2-(4-chloro-3-fluorophenoxy)acetamido]-N-[5-(difluoromethoxy)pyridin-2-yl]methyl}bicyclo[1.1.1]pentane-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 0.5h; N,N-Dimethylformamide (2 mL), triethylamine (0.079 mL, 0.57 mmol) and 1-[bis(dimethylamino)methylenej - 1H- 1 ,2,3-triazolo [4,5-bj pyridinium 3 -oxidhexafluorophosphate (79 mg, 0.208 mmol, HATU) were added to a mixture of the product of Example 1 8A (59.4 mg, 0.189 mmol) and (5-(difluoromethoxy)pyridin-2-yl)methanamine (Enamine, 33 mg, 0.189 mg) in sequential order. The reaction mixture was then stirred at ambient temperature for 30 minutes. The resulting solution was filtered through a glassmicrofiber fit and purified by preparative HPLC [YMC TriArtTM C18 Hybrid 5 lIm column, 50100 mm, flow rate 90 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)j to give the title compound (56 mg, 0.119 mmol, 63% yield). ?H NMR (501 MHz, DMSO-d6) 5 ppm 8.73 (s, 1H), 8.44 (t, J = 6.1 Hz, 1H), 8.40 (d, J = 2.8 Hz, 1H), 7.64 (dd, J = 8.6, 2.9 Hz, 1H), 7.50 (t, J8.9 Hz, 1H), 7.29 (dd, J = 8.6, 0.7 Hz, 1H), 7.27 (t, J = 73.5 Hz, 1H), 7.08 (dd, J = 11.4, 2.9 Hz, 1H), 6.86 (ddd, J = 8.9, 2.9, 1.2 Hz, 1H), 4.47 (s, 2H), 4.33 (d, J = 6.1 Hz, 2H), 2.22 (s, 6H); MS (ESI) m/z 470 (M+H).
  • 14
  • [ 50488-42-1 ]
  • [ 164341-39-3 ]
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; ;