Alternatived Products of [ 683274-61-5 ]
Product Details of [ 683274-61-5 ]
| CAS No. : | 683274-61-5 |
MDL No. : | MFCD03407524 |
| Formula : |
C15H20N4O2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
288.35
|
Pubchem ID : | - |
| Synonyms : |
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Safety of [ 683274-61-5 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 683274-61-5 ]
* 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 [ 683274-61-5 ]
- 1
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[ 149554-29-0 ]
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[ 683274-61-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate In dimethyl sulfoxide at 90℃; for 8h; |
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- 2
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[ 33252-28-7 ]
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[ 57260-71-6 ]
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[ 683274-61-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 73% |
With potassium carbonate In N,N-dimethyl acetamide at 20 - 60℃; for 6h; Inert atmosphere; |
11.1 Step-1
To a stirred solution of 6-chloropyridine-3-carbonitrile (2 g, 14.43 mmol) in DMA (20 mL),K2C03 (3.4 g, 24.63 mmol), N-Boc-piperazine (2.7 g, 14.50 mmol) were added at RT underargon atmosphere and stirred for 3 h. The reaction mixture was heated at 60 °C for 3 h (TLCindicated complete consumption of starting material) and poured into ice-water (100 mL)during which solid precipitated out which was filtered, washed with Et20 (3 x 10 mL),pentane (3 x 10 mL) and dried to afford tert-butyl4-(5-cyano-2-pyridyl)piperazine-1-carboxylate (3 g, 73%) which was used without purification.LCMS: mlz: 289.3 [M+Ht. |
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With potassium carbonate In ISOPROPYLAMIDE at 20 - 60℃; for 7h; |
140.1
The mixture of 702 mg of 6-chloronicotinonitrile, 954 mg of t-butylpiperazin-1-carboxylate, 1.2 g of potassium carbonate, and 10 mL of N,N-dimethylacetamide, was stirred at room temperature for 3 hours, then heated to 60°C and stirred further for 4 hours. After cooling the reaction mixture back to room temperature, water was added thereto, and was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and 1.39 g of t-butyl4-(5-cyanopyridin-2-yl)piperazin-1-carboxylate [140-1] was obtained as a white solid. |
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With N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 150℃; for 2h; Microwave irradiation; |
20.1
6- {4- [5 -(5 -chloro- 1 H-benzimidazol-2-yl)pyridin-2-yl3piperazin- 1 -yl } pyridine- 3 -carbonitrile Step 1: To a solution of 6-chloropyridine-3 -carbonitrile (300mg, 2.16mmol) and tert-butyl piperazine-l-carboxylate (403 mg, 2.16mmol) in DMA (3mL) was added N,N- diisopropylethylamine (840mg, 6.50mmol). The mixture was heated to 150° C in a microwave for 2 hours. The cooled mixture was partitioned between ethyl acetate and water. The organic layer was twice washed with water and dried over Na2S04 to give fert-butyl 4-(5-cyanopyridin- 2-yl)piperazine-l~carboxylate. LC-MS (M-BOC) =189. |
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With tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In dimethyl sulfoxide at 140℃; for 3h; |
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| 1.457 g |
With potassium carbonate In dimethyl sulfoxide at 90℃; |
38-1.1
General procedure: (1) Compound 1 (18.5 g), Compound 2 (20 g) and potassium carbonate (16.35 g) were added to dimethylsulfoxide (280 mL), and the mixture was stirred at 90 °C overnight. After the reaction solution was cooled, water and ethyl acetate were added to carry out a liquid separation. The organic layer was separated, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. To the obtained residue were added n-hexane and ethyl acetate, and the mixture was stirred, and subsequently, the solid was collected by filtration to obtain Compound 3 (23.21 g). (1) A treatment was carried out in a manner similar to the Example 37-1 (1) using Compound 1 (1.0 g) and Compound 2 (818 mg) to obtain Compound 3 (1.457 g). MS (m/z): 289 [M+H]+ |
| 195 g |
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 1h; |
1 Step 1: Tert-butyl 4-(5-cyanopyridin-2-yl)piperazine-1-carboxylate
A solution of 6-chloropyridine-3-carbonitrile (90 g, 650 mmol, 1.05 equiv), tert-butyl piperazine-1-carboxylate (114.3 g, 620 mmol, 1 equiv), and K2CO3 (171.1 g, 124 mmol, 2 equiv) in NMP (500 mL) was stirred for 1 h at 80° C. followed by the addition of 1.5 L of H2O which was added to the resulting solution. The solids were collected by filtration to afford 195 g of title compound as a white solid. LCMS: [M+H]+ 289.17 |
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With triethylamine In acetonitrile at 160℃; for 0.5h; Microwave irradiation; Inert atmosphere; |
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Reference：
[1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2018/125961, 2018, A1
Location in patent: Page/Page column 47
[2]Current Patent Assignee: MERCK & CO INC - EP1790650, 2007, A1
Location in patent: Page/Page column 89
[3]Current Patent Assignee: MERCK & CO INC - WO2012/64569, 2012, A1
Location in patent: Page/Page column 38
[4]Weiler, Sven; Braendlin, Nadine; Beerli, Christian; Bergsdorf, Christian; Schubart, Anna; Srinivas, Honnappa; Oberhauser, Berndt; Billich, Andreas
[Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5074 - 5084]
[5]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP2862856, 2015, A1
Location in patent: Paragraph 0565; 0574; 0575
[6]Current Patent Assignee: RIBON THERAPEUTICS INC; RIBON THERAPEUTICS INC - US2019/330194, 2019, A1
Location in patent: Paragraph 0573
[7]Sharma, Lalit Kumar; Yun, Mi Kyung; Subramanian, Chitra; Tangallapally, Rajendra; Jackowski, Suzanne; Rock, Charles O.; White, Stephen W.; Lee, Richard E.
[Bioorganic and Medicinal Chemistry, 2021, vol. 52]
- 3
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potassiumhexacyanoferrate(II) trihydrate
[ No CAS ]
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[ 153747-97-8 ]
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[ 683274-61-5 ]
- 4
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[ 683274-61-5 ]
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[ 149554-29-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride In 1,4-dioxane |
20.1
6- {4- [5 -(5 -chloro- 1 H-benzimidazol-2-yl)pyridin-2-yl3piperazin- 1 -yl } pyridine- 3 -carbonitrile Step 1: To a solution of 6-chloropyridine-3 -carbonitrile (300mg, 2.16mmol) and tert-butyl piperazine-l-carboxylate (403 mg, 2.16mmol) in DMA (3mL) was added N,N- diisopropylethylamine (840mg, 6.50mmol). The mixture was heated to 150° C in a microwave for 2 hours. The cooled mixture was partitioned between ethyl acetate and water. The organic layer was twice washed with water and dried over Na2S04 to give fert-butyl 4-(5-cyanopyridin- 2-yl)piperazine-l~carboxylate. LC-MS (M-BOC) =189. |
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With trifluoroacetic acid In dichloromethane at 20℃; for 3.5h; |
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With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Inert atmosphere; |
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Reference：
[1]Current Patent Assignee: MERCK & CO INC - WO2012/64569, 2012, A1
Location in patent: Page/Page column 38
[2]Weiler, Sven; Braendlin, Nadine; Beerli, Christian; Bergsdorf, Christian; Schubart, Anna; Srinivas, Honnappa; Oberhauser, Berndt; Billich, Andreas
[Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5074 - 5084]
[3]Sharma, Lalit Kumar; Yun, Mi Kyung; Subramanian, Chitra; Tangallapally, Rajendra; Jackowski, Suzanne; Rock, Charles O.; White, Stephen W.; Lee, Richard E.
[Bioorganic and Medicinal Chemistry, 2021, vol. 52]
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