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[ CAS No. 109384-19-2 ]

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2D
Chemical Structure| 109384-19-2
Chemical Structure| 109384-19-2
Structure of 109384-19-2 *Storage: {[proInfo.prStorage]}

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Product Details of [ 109384-19-2 ]

CAS No. :109384-19-2MDL No. :MFCD01075174
Formula : C10H19NO3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :201.26Pubchem ID :643502
Synonyms :

Computed Properties of [ 109384-19-2 ]

TPSA : 49.8 H-Bond Acceptor Count : 3
XLogP3 : 1 H-Bond Donor Count : 1
SP3 : 0.90 Rotatable Bond Count : 2

Safety of [ 109384-19-2 ]

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 [ 109384-19-2 ]

  • Downstream synthetic route of [ 109384-19-2 ]

[ 109384-19-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 10320-42-0 ]
  • [ 109384-19-2 ]
  • [ 862313-62-0 ]
YieldReaction ConditionsOperation in experiment
54% With cesium fluoride; In N,N-dimethyl-formamide; at 20℃; for 24h; Cesium fluoride (17.8 g, 117.5 mmol) was added to a solution of 2-chloro-5-nitro- pyrimidine (12.5 g, 78.3 mmol) and tert-butyl 4-hydroxypiperidine-l-carboxylate (15.8 g, 78.3 mmol) in DMF (375 mL). The resulting mixture was stirred for 24 h at room temperature. The insoluble solids were removed by filtration were filtred through a short pad of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed successively with water (150 mL) and brine (50 mL). The organic layer was dried over MgS04, filtered and concentrated to dryness. Purification by flash chromatography over silica gel (gradient of EtOAc in heptane from 0 to 35percent) gave the pure compound 9a as a white solid (13.9 g, 54percent). MR (300 MHz, Chloroform-i ) delta 1.47 (s, 9H), 1.76 - 1.92 (m, 2H), 1.98 - 2.13 (m, 2H), 3.21 - 3.44 (m, 2H), 3.63 - 4.00 (m, 2H), 5.26 - 5.50 (m, 1H), 9.29 (s, 2H). MS m/z 269 (M+H-tBu)+.
38% With cesium fluoride; In DMF (N,N-dimethyl-formamide); at 20℃; for 12h; Example 226 3-{(2-[(1-cyclobutylpiperidin-4-yl)oxy]-pyrimidin-5-yl}-2-methyl-5-(trifluoromethyl)-4(3H)-quinazolinone (1) Manufacture of t-butyl-4-[(5-nitroglycerine-pyrimidin-2-yl)oxy]piperidine-1-carboxylate 2-chloro-5-nitroglycerine-pyrimidine (80 mg, 0.5 mmol), t-butyl-4-hydroxypiperidine-1-carboxylate (100 mg, 0.5 mmol) and cesium fluoride (114 mg, 0.75 mmol) were mixed in dimethylformamide, and stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, the product was purified by silica gel column chromatography (hexane/ethyl acetate=10/0-3/7), and the target compound (61 mg, 38%) was thus obtained as a light yellow solid.
30% With cesium fluoride; In N,N-dimethyl-formamide; at 20℃; for 24h; Cesium fluoride (5.71 g, 37.6 mmol) was added to a solution of 2-Chloro-5-nitro- pyrimidine (4.0 g, 25.0 mmol) and 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 25.0 mmol) in DMF (120 mL). The resulting mixture was stirred for 24 h at roomtemperature. The insolubles were collected by filtration through a short pad of diatomaceous earth. The filtrate was concentrated under reduced pressure. The residue was taken in EA (40 mL) and washed successively with water (40 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated to dryness. Chromatography over silica gel (gradient of EA in heptane from 0 to 35%) gave the pure product as a white solid (2.43 g, 30%). ?H NMR (300 IVIFIz, Chloroform-cl) 1.47 (s, 9H),1.76- 1.92 (m, 2H), 1.98-2.13 (m, 2H), 3.21 -3.44 (m, 2H), 3.63 -4.00 (m, 2H), 5.26-5.50 (m, 1H), 9.29 (s, 2H). MS m/z 269 C,4H20N405 (M+H-tBu).
  • 2
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  • [ 1058702-84-3 ]
  • 3
  • [ 109384-19-2 ]
  • [ 71902-33-5 ]
  • [ 1189551-57-2 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 17h; t-Butyl 4-hydroxypiperidine-1-carboxylate (1.04 g, 5.00 mmol) was added to a N,N-dimethylformamide suspension (5.0 ml) of 60percent sodium hydride (229 mg, 6.00 mmol), at 0°C, and stirring was carried out at room temperature for 30 minutes. Further, at 0°C, <strong>[71902-33-5]3,5-difluoropyridine</strong> (645 mg, 5.50 mmol) was added, and stirring was carried out for 16.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed sequentially with water and saline, and then dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by silica gel column chromatography to afford t-butyl 4-[(5-fluoropyridin-3-yl)oxy]piperidine-1-carboxylate (1.48 g, yield 99percent) as a colorless oil. 1H-NMR (CDCl3, 400 MHz) delta: 8.16-8.11 (2H, m), 6.96 (1H, dt, J=10.2, 2.3 Hz), 4.52-4.47 (1H, m), 3.73-3.67 (2H, m), 3.39-3.33 (2H, m), 1.99-1.73 (4H, m), 1.47 (9H, s). MS (ESI, m/z): 297 (M+H)+.
  • 4
  • [ 109384-19-2 ]
  • [ 147754-12-9 ]
  • [ 1164178-34-0 ]
YieldReaction ConditionsOperation in experiment
92% a) 1.35 g 4-Fluoro-2-methyl-benzonitrile, dissolved in DMF, was added to 2.11 g 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester and 0.6 g sodium hydride in 30 mL DMF. The mixture was stirred at room temperature (rt) until the reaction was complete. The reaction was quenched with water. The aqueous layer was extracted with ethylacetate (AcOEt) or methyl tert. butyl ether (MTB ether). The combined organic layers were washed with brine, dried and concentrated to to give 2.6 g (yield 81percent) 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. Mass: (C18H24N2O3): calcd. 316, found 261 [M+H-t(C4H9)]+
92% 1 ) 4-(4-Cvano-3-methvi-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester b) 22.6 g Potassium tert. butoxide, 33.2 g 4-Hydroxy-piperidine-1-carboxylic acid tert- butyl ester and 300 mL MTB ether were stirred for 1h at reflux. A solution of 20.3 g 4- Fluoro-2-methyl-benzonitrile, dissolved in 250 mL MTB ether was added within 20 min to the suspension and heating to reflux was continued for 7 h. The reaction was quenched with water. The organic layer was separated and washed with water and concentrated to give 54.8 g (yield 92percent) of 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1- carboxylic acid tert-butyl ester. H NMR (500 MHz, d6-DMSO) delta 1.40 (s, 9H), 1.47-1.55 (m, 2H), 1.88-1 .95 (m, 2H), 2.43 (s, 3H), 3.13-3.22 (m, 2H), 3.63-3.70 (m, 2H), 4.66- 4.73 (m, 1 H), 6.96 (dd, J = 8.6, 2.4 Hz, 1 H), 7.07 (d, J = 2.3 Hz, 1 H), 7.67 (d, J = 8.7 Hz, 1 H).
  • 5
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  • [ 147754-12-9 ]
  • [ 1417697-15-4 ]
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