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[ CAS No. 16085-45-3 ] {[proInfo.proName]}

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Chemical Structure| 16085-45-3
Chemical Structure| 16085-45-3
Structure of 16085-45-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16085-45-3 ]

CAS No. :16085-45-3 MDL No. :MFCD06245150
Formula : C11H13F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 230.23 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 16085-45-3 ]

* 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 [ 16085-45-3 ]

[ 16085-45-3 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
11 II. III-11. 4-(1-pyrrolidinyl)-3-(trifluoromethyl)aniline MS (ESI): m/z (%)=231 (M+H, 100); HPLC (method 7): rt=3.40 min.
11 III-11. III-11. 4-(1-Pyrrolidinyl)-3-(trifluoromethyl)aniline MS (ESI): m/z (%)=231 (M+H, 100);
  • 2
  • [ 16085-45-3 ]
  • [ 6541-19-1 ]
  • 9-(pyrrolidin-1-yl)-10-(trifluoromethyl)pyrido[2,3-b]phenazine-5,12-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 4-(pyrrolidin-1-yl)-3-(trifluoromethyl)aniline; 6,7-dichloroquinoline-5,8-dione With cerium(III) chloride heptahydrate In ethanol at 60 - 80℃; for 2h; Stage #2: With sodium azide In water; N,N-dimethyl-formamide at 90℃; for 2h; II.80 Example 80: 9-(pyrrolidin-l-yl)-10-(trifluoromethyl)pyrido[2,3-b]phenazine-5,12-dione (80). Following general protocol J. A solution of 6,7-dichloro-5,8-quinolinediones (0.1 equiv.), cerium(III) chloride heptahydrate (CeCb-7 H2O, 0.11 equiv.) and 4-(pyrrolidin-l-yl)- 3-(trifluoromethyl)aniline (23.0 mg, 0.1 mmol) in ethanol (2 mL) was stirred at 60-80 °C for 2 h. Next, most of the ethanol was removed under vacuum. Then DMF (2 mL), H2O (10 pL) and sodium azide (13 mg, 0.2 mmol) were added to above reaction system. The mixture solution was stirred at 90 °C for 2 h. The reaction mixture was chilled, the filtered precipitate was extracted with methylene chloride and concentrated, and then the residue was purified by column chromatography, 9-(pyrrolidin-l-yl)-10-(trifluoromethyl)pyrido[2,3-b]phenazine- 5,12-dione was recovered as a dark purple solid (7.2 mg, 18% yield). ' H NMR (400 MHz, Methanol-c 4) d 9.11 (d, J= 4.5 Hz, 1H), 8.81 (dd, J = 7.9, 1.7 Hz, 1H), 8.12 (d, J= 9.8 Hz, 1H), 8.03 - 7.91 (m, 2H), 3.76 (s, 4H), 2.14 - 2.03 (m, 4H). LCMS (ESI) 399.00 [M + H]+. HPLC purity at 254 nm, 99.2%.
  • 3
  • [ 16085-45-3 ]
  • [ 6541-19-1 ]
  • 9-(pyrrolidin-1-yl)-8-(trifluoromethyl)pyrido[2,3-b]phenazine-5,12-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% Stage #1: 4-(pyrrolidin-1-yl)-3-(trifluoromethyl)aniline; 6,7-dichloroquinoline-5,8-dione With cerium(III) chloride heptahydrate In ethanol at 60 - 80℃; for 2h; Stage #2: With sodium azide In water; N,N-dimethyl-formamide at 90℃; for 2h; II.81 Example 81: 9-(pyrrolidin-l-yl)-8-(trifluoromethyl)pyrido[2,3-b]phenazine-5,12-dione (81). Following general protocol J. A solution of 6,7-dichloro-5,8-quinolinediones (0.1 equiv.). cerium(III) chloride heptahydrate (CeCb 7 H2O, 0.11 equiv.) and 4-(pyrrolidin-l-yl)-3- (trifluoromethyl)aniline (23.0 mg, 0.1 mmol) in ethanol (2 mL) was stirred at 60-80 °C for 2 h. Next, most of the ethanol was removed under vacuum. Then DMF (2 mL), H2O (10 pL) and sodium azide (13 mg, 0.2 mmol) were added to above reaction system. The mixture solution was stirred at 90 °C for 2 h. The reaction mixture was chilled, the filtered precipitate was extracted with methylene chloride and concentrated, and then the residue was purified by column chromatography, 9-(pyrrolidin-l-yl)-8-(trifluoromethyl)pyrido[2,3-b]phenazme-5,12- dione was recovered as a dark purple solid (6.0 mg, 15% yield). NMR (400 MHz, Methanol-cri) d 9.12 (dd, J= 4.7, 1.7 Hz, 1H), 8.84 (dd, J= 8.0, 1.7 Hz, 1H), 8.61 (s, 1H), 8.01 (dd, J= 8.0, 4.7 Hz, 1H), 7.57 (s, 1H), 3.70 (t, J= 6.3 Hz, 4H), 2.23 - 2.08 (m, 4H). LCMS (ESI) 399.00 [M + H]+. HPLC purity at 254 nm, 98.4%.
  • 4
  • [ 16085-45-3 ]
  • 4-(benzyloxy)-3-(1,3-dithian-2-yl)-5-fluorobenzoic acid [ No CAS ]
  • 3-fluoro-5-formyl-4-hydroxy-N-(4-(pyrrolidin-1-yl)-3-(trifluoromethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / 2 h / 20 °C 1.2: 3 h / 20 °C 2.1: sodium hydrogencarbonate / water; acetonitrile / 2 h / 40 °C 2.2: 20 °C
  • 5
  • [ 16085-45-3 ]
  • 4-(benzyloxy)-3-(1,3-dithian-2-yl)-5-fluorobenzoic acid [ No CAS ]
  • 4-(benzyloxy)-3-(1,3-dithian-2-yl)-5-fluoro-N-(4-(pyrrolidin-1-yl)-3-(trifluoromethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 4-(benzyloxy)-3-(1,3-dithian-2-yl)-5-fluorobenzoic acid With oxalyl dichloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 4-(pyrrolidin-1-yl)-3-(trifluoromethyl)aniline With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; B48.3 Benzyl bromide (BnBr) (3.62 g, 21.2 mmol, 2.0 eq.) was added to a solution of 3- (l,3-dithian-2-yl)-5-fluoro-4-hydroxybenzoic acid (2.9 g, 10.6 mmol, 1.0 eq.) and potassium carbonate (2.9 g, 21.0 mmol, 2.0 eq.) in DMF (25 mL). The mixture was stirred for 3 hours at room temperature and poured into water. The mixture was then extracted with ethyl acetate for three times. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude bis-Bn protected ester (3.1 g, 6.8 mmol, 64% yield) as light yellow solid. The ester (3.1 g, 6.8 mmol, 1.0 eq.) was mixed with LiOH.FbO (833 mg, 20.5 mmol, 3 eq.) in THF/water (5 mF/5 mL). The reaction was stirred for 2 hours at room temperature. Then pH of the reaction system was acidified to 3-4 and the mixture was extracted with ethyl acetate for three times. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was crystallized in ethyl acetate/petroleum ether to give 4-(benzyloxy)-3-(l,3-dithian-2-yl)-5-fluorobenzoic acid (1.5 g, 4.1 mmol, 60% yield) as white solid. The resulting 4-(benzyloxy)-3-(l,3-dithian-2-yl)-5- fluorobenzoic acid (445 mg, 1.2 mmol, 1.0 eq.) was dissolved in dichloromethane (10 mL) and oxalyl chloride (311 mg, 2.4 mmol, 2.0 eq.) and DMF (1 drop) was added. The reaction was stirred for 2 hours at room temperature. The solvent was removed in vacuo and the residue was co-evaporated with dichloromethane for two times. The residue was then dissolved in dichloromethane and the solution was cooled to 0°C. Then, 4-(pyrrolidin-l-yl)-3- (trifluoromethyl)aniline (309 mg, 1.3 mmol, 1.1 eq.) and TEA (369 mg, 3.6 mmol, 3.0 eq.) were added successively. The reaction was stirred for 3 hours at room temperature. The solution was poured into water and extracted with dichloromethane for two times. The organic extracts were washed with 1 % KHS04, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=20:lto 5:1) to give 4-(benzyloxy)-3-(l,3-dithian-2-yl)-5-fluoro-N-(4-(pyrrolidin-l-yl)-3- (trifluoromethyl)phenyl)benzamide (370 mg, 0.64 mmol, 53% yield) as a yellow powder. LC- MS m/z [M+H]+ calc’d for C29H28F4N2O2S2, 577; found, 577.
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