Alternatived Products of [ 167414-75-7 ]
Product Details of [ 167414-75-7 ]
| CAS No. : | 167414-75-7 |
MDL No. : | MFCD04115570 |
| Formula : |
C18H23NO5
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | HSYRPXCJJXOCKE-UHFFFAOYSA-N |
| M.W : |
333.38
|
Pubchem ID : | 10449485 |
| Synonyms : |
|
Safety of [ 167414-75-7 ]
Application In Synthesis of [ 167414-75-7 ]
* 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.
- Upstream synthesis route of [ 167414-75-7 ]
- Downstream synthetic route of [ 167414-75-7 ]
- 1
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[ 167414-75-7 ]
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3-<1-(benzyloxycarbonyl)-4-piperidyl>isoxazol-5-ol
[ No CAS ]
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5-<(1-benzyloxycarbonyl)-4-piperidyl>isoxazol-3-ol
[ No CAS ]
- 2
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[ 10314-98-4 ]
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2.) <3-ethoxy-3-hydroxyacrylato(2-)-O1,O3>magnesate(2+)
[ No CAS ]
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[ 167414-75-7 ]
- 3
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[ 167414-75-7 ]
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3-(4-piperidyl)isoxazol-5-ol hydrobromide
[ No CAS ]
- 4
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[ 17356-08-0 ]
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[ 167414-75-7 ]
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6-(1-(benzyloxycarbonyl)piperidin-4-yl)-2,4-dihydroxypyrimidine
[ No CAS ]
- 6
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[ 50-01-1 ]
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[ 167414-75-7 ]
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[ 1115491-17-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 84% |
|
REFERENCE EXAMPLE 3; Benzyl 4-(2-amino-6-hydroxypyrimidin-4-yl)piperidin-1-carboxylate; Guanidine hydrochloride (2.15 g, 22.5 mmol) and sodium ethoxide (7.3 g of a 21 percent solution in etanol, 22.5 mmol) were added to a solution of benzyl 4-(3-ethoxy-3- oxopropanoyl)piperidin-1 -carboxylate (5.0 g, 15 mmol) in absolute etanol (150 mL) and the mixture was heated at reflux overnight. The solvent was concentrated to dryness, the residue was diluted with water and the pH was adjusted to 6-7 with 1 N HCI. The suspension was stirred at temperature for 2 hours. The precipitated solids were filtered, they were washed with abundant water and then with diethyl ether and they were dried in a vacuum, providing 4.13 g of the title compound (yield: 84percent) LC-MS (Method 2): tR = 1.51 min; m/z = 329 (MH+). |
- 7
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[ 141-78-6 ]
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[ 10314-99-5 ]
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[ 167414-75-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
Step 3To a 250 mL three necked round bottom flask, n-BuLi (23percent solution in hexane) (18.52 mL) was added to a solution of diisopropyl amine (8.13 mL) in THF (50 mL) at -78° C. The reaction mixture was warmed to 0 °C and stirred for 30 min and again cooled to-78° C. Dry ethyl acetate (6.5 mL) was added and after 30 min at -78° C, a solution of benzyl 4- (chlorocarbonyl)piperidine-l-carboxylate in THF (10 mL) was added and stirred for 1 h at- 78° C. The completion of the reaction was monitored on TLC using ethyl acetate: hexanes (3:7) as a mobile phase. After completion of the reaction, the reaction mixtures was warmed to RT and acidify using IN HC1. The product was extracted in ethyl acetate. The combined organics were washed with water, dried over sodium sulphate and evaporated to afford yellowish oil (crude) product which was purified using column purification by eluting with 10-15 percent ethyl acetate in hexane to give benzyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l- carboxylate 7.0 g. |
- 8
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[ 498-94-2 ]
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[ 167414-75-7 ]
- 9
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[ 501-53-1 ]
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[ 167414-75-7 ]
- 10
-
[ 10314-98-4 ]
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[ 167414-75-7 ]
- 11
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[ 167414-75-7 ]
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[ 1266159-39-0 ]
- 12
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[ 167414-75-7 ]
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[ 1266160-29-5 ]
- 13
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[ 167414-75-7 ]
-
[ 1413943-82-4 ]
- 14
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[ 167414-75-7 ]
-
[ 1413943-84-6 ]
- 15
-
[ 167414-75-7 ]
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[ 1413943-85-7 ]
- 16
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[ 1266161-61-8 ]
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[ 167414-75-7 ]
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[ 1413943-83-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
In ISOPROPYLAMIDE; at 250℃; for 0.166667h;Microwave irradiation; |
Step 4To a 35 mL microwave vessel, 3-amino-3-(4-phenoxyphenyl)acrylonitrile (1.0 g, 4.2 mmol) and benzyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l-carboxylate (3.5 g, 10.5 mmol) were taken in N,N-dimethylacetamide (7.5 mL) and heated at 250° C for 10 min in microwave. The completion of the reaction was monitored on TLC using ethyl acetate: hexanes (3:7) as a mobile phase. The above reaction was repeated and combined. The combined reaction mixture was cooled to the room temperature, diluted with water and the solid was filtered and washed with water to get benzyl 4-(5-cyano-4-oxo-6-(4- phenoxyphenyl)- 1 ,4-dihydropyridin-2-yl)piperidine- 1 -carboxylate 1.8 g. |
- 17
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[ 6148-64-7 ]
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[ 10314-98-4 ]
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[ 167414-75-7 ]
- 18
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[ 62538-16-3 ]
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[ 167414-75-7 ]
-
benzyl 4-(3-(4-fluorophenyl)-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate
[ No CAS ]
- 19
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[ 167414-75-7 ]
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[ 214416-39-4 ]
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benzyl 4-(3-(4-chlorophenyl)-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate
[ No CAS ]
- 20
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[ 1264296-30-1 ]
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[ 167414-75-7 ]
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C27H25F3N4O3
[ No CAS ]
- 21
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3-methyl-4-(4-nitrophenyl)-1H-pyrazol-5-amine
[ No CAS ]
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[ 167414-75-7 ]
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C26H25N5O5
[ No CAS ]
- 22
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C11H11FN2
[ No CAS ]
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[ 167414-75-7 ]
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C25H23FN4O3
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
With acetic acid; at 130℃; |
Intermediate 5, 3.8 g (20 mmol), intermediate 3 7.99 g (24 mmol) was added to a 50 mL round bottom flask. Add 20 mL of acetic acid to dissolve, and react at 130 °C overnight. After the reaction is completed, the acetic acid is removed by rotary evaporation. 1M NaOH was added dropwise to precipitate a large amount of off-white solid, which was filtered. Washing with a small amount of MeOH gave a white solid M086. Yield 75.0percent. |
- 23
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C17H19N3O3
[ No CAS ]
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[ 6148-64-7 ]
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[ 167414-75-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
6.8 g (40 mmol) of monoethyl malonate potassium salt was added to a 500 mL round bottom flask, 100 mL of freshly distilled THF and 50 mL of re-steamed CH3CN were added, and the temperature was lowered to 0 °C. Anhydrous MgCl2 3.8 g (40 mmol) and DMAP 244 mg (2 mmol) were added. Stir to room temperature and stir for 6 h. Cool down to 0 ° C, Intermediate 2 6.26 g (20 mmol) was dissolved in 10 mL of freshly-purified THF, and Et3N 3.03 g (40 mmol) was added dropwise to a round bottom flask, and the mixture was slowly warmed to room temperature and stirred overnight. After the reaction was completed, the temperature was lowered to 0 ° C, and 150 mL of 1 HCl was added thereto, and extracted with Et 2 O (100 mL×3), and the Et 2 O phase was washed with saturated brine. Dry over anhydrous MgSO4, The mixture was filtered and dried, and the product was separated into a pale yellow oily liquid by separating the column with 200-300 mesh silica gel. The yield in two steps is 85.75percent. |
- 24
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C11H11ClN2
[ No CAS ]
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[ 167414-75-7 ]
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benzyl 4-(3-(4-chlorophenyl)-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 84.57% |
With acetic acid; at 130℃; |
Intermediate 5, 4.12 g (20 mmol), intermediate 3, 7.99 g (24 mmol)was added to a 50 mL round bottom flask, add 20 mL of acetic acid to dissolve, and reacted at 130 °C overnight. After the reaction is completed, the acetic acid is removed by steaming. A large amount of an off-white solid was precipitated by dropwise addition of 1 NaOH. The yield is 84.57percent. |
- 25
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[ 4677-20-7 ]
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[ 167414-75-7 ]
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benzyl 4-(3-ethoxy-2- [2-(oxan-4-yl)ethyl]-3-oxopropanoyl)piperidine-1-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 67% |
With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 70℃; for 3h; |
A stirred mixture b-ketoester 7 (550 mg, 1.65 mmol), bromide 8 (335 mg, 1.73 mmol), KI (302 mg, 1.8 mmol), K2CO3 (251 mg, 1.8 mmol) and dry DMF (5 mL) was heated at 70 C for 3 h. The mixture was diluted with EtOAc (90 mL), washed with 1% aq HC1 (15 mL) and brine (15 mL), and dried over Na2S04. Removal of the solvent left a yellow oil (1.34 g) which was chromatographed on a 12 g silica cartridge, eluted with a 0 - 70% EtOAc in hexanes gradient, to give P3-001 (495 mg, 67% yield). LC-MS tR 5.41 min, m/z 446. |
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