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Chemical Structure| 101799-75-1 Chemical Structure| 101799-75-1

Structure of 101799-75-1

Chemical Structure| 101799-75-1

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Product Details of [ 101799-75-1 ]

CAS No. :101799-75-1
Formula : C14H13F3O4
M.W : 302.25
SMILES Code : C(C1C=C(C(=CC=1F)F)F)(=O)C(=COCC)C(=O)OCC
MDL No. :MFCD28502721

Safety of [ 101799-75-1 ]

Application In Synthesis of [ 101799-75-1 ]

* 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 [ 101799-75-1 ]

[ 101799-75-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 2247-88-3 ]
  • [ 101799-75-1 ]
  • [ 164151-35-3 ]
  • 2
  • [ 101799-75-1 ]
  • [ 93107-30-3 ]
  • 3
  • [ 247069-27-8 ]
  • [ 101799-75-1 ]
  • (E)-1-(6-amino-3,5-difluoropyridin-2-yl)-6-fluoro-7-(3-isobutyryloxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
  • (Z)-1-(6-amino-3,5-difluoropyridin-2-yl)-6-fluoro-7-(3-isobutyryloxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
  • 4
  • [ 247069-27-8 ]
  • [ 101799-75-1 ]
  • 1-(6-amino-3,5-difluoropyridin-2-yl)-6-fluoro-7-(3-isobutyryloxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.9 g In acetonitrile; at 10 - 30℃; (2) Compound A-2 (5 g, 20.3 mmol), triethylorthoformate (10 ml) and acetic anhydride (6 ml) were mixed and stirred, and the temperature was raised to 120-130C. The mixture was stirred for 4 hours, and the reaction was completely cooled down to 15 - The mixture was stirred at 25 C, added with water (30 ml) and ethyl acetate (30 ml) for 10 minutes. The mixture was extracted with liquid and the organic phase was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure and dissolved in acetonitrile (20 ml). A mixture of diamino-3,5-difluoropyridine (3.2 g, 22.3 mmol) and acetonitrile (20 ml) was added dropwise, and the temperature was controlled at 10-30C for 1-2 hours. The reaction was complete, the temperature was lowered, an appropriate amount of water was added, filtered, and dried to give 7.9 g of Compound A-3, HPLC 97.4%, and Compound 12.3%. Yield 97%.
  • 5
  • [ 101799-75-1 ]
  • [ 143062-84-4 ]
  • 2-(2,4,5-trifluorobenzoyl)-3-[(1R,2S)-2-fluorocyclopropyl]amino}acrylate ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 2h; General procedure: A solution of keto esters 4a-d (1 mmol) and triethyl orthoformate (2.50 mL, 1.5 mmol) in acetic anhydride (5.5 mL, 6 mmol) was stirred for 8 h at reflux and concentrated under reduced pressure to give crude products 5a-d as yellow oils. To a solution of 5a-d and triethylamine (2.80 mL, 2 mmol) dissolved in dichloromethane (10 mL) was added (1R,2S)-fluorocyclopropanaminetosylate (3.71 g, 1.5 mmol) in portions and stirred for 2 h at room temperature, and then concentrated under reduced pressure togive crude products 6a-d as yellow oils. A mixture of 6a-d, DMF (10 mL) and K2CO3 (2.80 g, 2 mmol) was stirred for 1 h at 90 oC and then poured into water (100 mL). The precipitate was collected by filtration and purified by silica gel column chromatography to give the title compounds 7a-d (42.5-61.3percent, from 4a-d) as white solids.
  • 6
  • [ 247069-27-8 ]
  • [ 18621-18-6 ]
  • [ 101799-75-1 ]
  • [ 77-92-9 ]
  • [ 442526-91-2 ]
YieldReaction ConditionsOperation in experiment
93.58% Ethyl 2,4,5-trifluorobenzoylacetate (20.0 g, 0.081 mol) was added to a 250 mL reaction flask.Triethylorthoformate (21.6 mL, 0.130 mol), acetic anhydride (32.5 mL, 0.344 mol), stirring,Heating was started and the temperature of the feed was raised to 130 C. for 4.0 hours.After the reaction was completed, the solvent was distilled off under reduced pressure to obtain an oily liquid.Add 70 mL of N-methylpyrrolidone to make the oily liquidThe solution was dissolved, <strong>[247069-27-8]3,5-difluoro-2,6-diaminopyridine</strong> (13.8 g, 0.095 mol) was added, and the feed solution was warmed to 50C.Stir and stir for 1.5h. After the addition of anhydrous lithium chloride (6.12 g, 0.146 mol), DBU (11.37 g, 0.075 mol) was added, and the reaction temperature was controlled at 35 C. for 2.0 h.3-Hydroxyazetidine hydrochloride (8.45 g, 0.077 mol) was added, DBU (26.82 g, 0.176 mol) was slowly added, and the temperature was 35 C. for 2.5 h.After the reaction is complete, transfer to a 500 mL reaction flask and add 25 mL of ethyl acetate.Slowly add 145 mL of 10% citric acid solution.After the addition was completed, the temperature was adjusted to 20C, and the crystals were crystallized for 4.0 hours. The crystals were collected, and the mixture was collected by suction filtration. The cake was collected and dried in an oven at 60C to obtain 38.35 g of the intermediate I. The yield was 93.58%.
  • 7
  • [ 247069-27-8 ]
  • [ 101799-75-1 ]
  • diethyl (2Z,2'Z)-3,3'-((3,5-difluoropyridine-2,6-diyl)bis(azanediyl))bis(2-(2,4,5-trifluorobenzoyl)acrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
4 g In water; acetonitrile; at 60 - 70℃; for 10h; (1) Compound A-2 (5 g, 20.3 mmol), triethylorthoformate (10 ml), acetic anhydride (6 ml) were mixed and stirred, and the temperature was raised to 120-130C, and the mixture was stirred for 4 hours. The reaction was completely cooled down to 15C. Acetonitrile (20 ml) was added at 25C, water (3 ml) was stirred for 10 minutes, and it was added dropwise to 2,4-diamino-3,5-difluoropyridine (1.2 g, 8.1 mmol), acetonitrile (20 ml). In the reaction flask, after completion of the dropwise addition, the temperature was raised to 60 to 70C and stirred for 10 hours. The reaction was complete, cooled, filtered and dried to give Compound 1 (4.0 g) in a yield of 75.1%. ESI-MS: [M+H]+658.
 

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