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CAS No. : | 907544-20-1 | MDL No. : | MFCD17976872 |
Formula : | C10H19FN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZQRYPCAUVKVMLZ-JGVFFNPUSA-N |
M.W : | 218.27 | Pubchem ID : | 11736104 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: (3S,4R)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate; 3,4-di-chloro-5-methyl-1H-pyrrole-2-carboxylic acid With 4-methyl-morpholine; benzotriazol-1-ol In dichloromethane for 0.25h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | |
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide 2: hydrogenchloride / 1,4-dioxane | ||
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0.25 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: hydrogenchloride / water; 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With tributyl-amine; In butan-1-ol; for 24h;Reflux; | To a solution of 25 (20.1 g, 92.1 mmol) and ethyl 4-chloro-1Hpyrrolo[2,3-b]pyridine-5-carboxylate (27) (13.8 g, 61.4 mmol) inn-BuOH (69 mL), n-Bu3N (29.3 mL, 123 mmol) was added, andthe mixture was stirred under reflux for 24 h. After cooling in anice bath, the precipitate was filtrated and successively washed withn-BuOH, IPE, and n-hexane to give the title compound (23.0 g,92%). 1H NMR (400 MHz, DMSO-d6) d 1.32 (3H, t, J = 7.2 Hz), 1.41(9H, s), 1.54-1.69 (1H, m), 1.89-1.97 (1H, m), 2.72-3.44 (2H, m),3.92-4.08 (1H, m), 4.17-4.52 (4H, m), 4.82-5.01 (1H, m), 6.66-6.70 (1H, m), 7.24-7.27 (1H, m), 8.58 (1H, s), 9.06 (1H, d,J = 8.8 Hz), 11.79 (1H, br s). MS (ESI) m/z: 407 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 25℃; for 4h;Inert atmosphere; | DIPEA (5.19 mL, 29.78 mmol) was added portionwise to <strong>[51940-64-8]ethyl 2,4-dichloropyrimidine-5-carboxylate</strong> (5.06 g, 22.91 mmol) and tert-butyl (3S,4R)-4-amino-3-fluoropiperidine-1-carboxylate(5.00 g, 22.91 mmol) in acetonitrile (100 mL) at 0C. The reaction mixture was stirred at rt for 4 h,then concentrated in vacuo, diluted with EtOAc (200 mL) and washed sequentially with water (1 00mL) and sat. brine (100 mL). The organic layer was filtered through a phase separating filter paper20 and concentrated in vacuo. The resulting crude product was purified by fcc, elution gradient 0 to50% EtOAc inn-heptane, to afford the title compound (4.87 g, 53%) as a white crystalline solid;1H NMR (400 MHz, DMSO) 1.32 (3H, t), 1.41 (9H, s), 1.56- 1.67 (lH, m), 1.82 (lH, d), 2.93 (lH,s), 4.01 (lH, s), 4.33 (5H, q), 4.86 (lH, d), 8.53 (lH, d), 8.69 (lH, s); m/z MH+ 403. |
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