Alternatived Products of [ 83405-70-3 ]
Product Details of [ 83405-70-3 ]
| CAS No. : | 83405-70-3 |
MDL No. : | MFCD02278306 |
| Formula : |
C10H16N2O2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | RCXMILPYEKVQLB-UHFFFAOYSA-N |
| M.W : |
196.25
|
Pubchem ID : | 2743509 |
| Synonyms : |
|
Application In Synthesis of [ 83405-70-3 ]
* 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 [ 83405-70-3 ]
- 1
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[ 13395-36-3 ]
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[ 83405-70-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 70% |
With hydrazine; In ethanol; at 20℃; |
Hydrazine hydrate (446 mmol) is added dropwise to solution of 5,5-dimethyl-2,4-dioxo- hexanoic acid ethyl ester (360 mmol) in ethanol at room temperature. After addition, the reaction mixture is stirred overnight at room temperature. On completion, the solvent is removed under reduced pressure and the residue obtained is diluted with water (250 mL) and extracted with dichloromethane (250 mL x are3). The combined organic phases are washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford 5-tert-butyl-2H- pyrazole-3-carboxylic acid ethyl ester as a white crystalline solid (70%).[0207] 1H NMR (400 MHz, DMSO-d6) delta: 13.21 (bs, IH), 6.45 (s, IH), 4.23 (q, 2H), 1.27 (s,9H,)1.25 (t, 3H). Mass (m/z): 197 (M+H). |
| 11 g |
With hydrazine dihydrochloride; In ethanol; for 3h;Reflux; |
General procedure: To a stirred solution of appropriate methyl ketone (0.1 mol) in dry toluene (200 mL)was added a suspension of NaH in mineral oil (60%; 0.2 mol) in portions and the mixture was warmed to50 C. At this temperature a solution of diethyl oxalate (0.15 mol) in dry toluene (60 mL) was addeddropwise under stirring. The reaction mixture was refluxed for 1.5 h. Upon cooling to room temperatureacetic acid (0.25 mol) was added dropwise. The reaction mixture was washed with water (200 mL), organicphase was dried over MgSO4 and evaporated to dryness. The obtained crude diketone was dissolved inethanol (250 mL), hydrazine dihydrochloride (0.11 mol) was added and the mixture was refluxed for 3 h.After evaporation of solvent the residue was treated with water (200 mL) and kept under ice-cooling for 1 h.Crystals were filtered off and dried in air to afford the corresponding pyrazole. In some cases thus obtainedsubstance was purified by recrystallization from aqueous ethanol. |
Reference：
[1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4383 - 4388
[2]Patent: WO2009/71706,2009,A1 .Location in patent: Page/Page column 43
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4914 - 4919
[4]Synlett,2018,vol. 29,p. 890 - 893
- 2
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[ 13395-36-3 ]
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[ 83405-70-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
With hydrazine; In ethanol; at 0 - 20℃; for 3h; |
To a solution of methyl 5,5-dimethyl-2,4-dioxohexanoic acid ethyl ester (720mmol) in ethanol (500 mL) is added dropwise, at 00C, hydrazine hydrate (640 mmol) and it is stirred for 3h at room temperature. On complete reaction, the mixture is diluted with water (1 L) and stirred for lOmin. The precipitate is collected by filtration and dried at room temperature for 5 hours. The product is isolated as an off- white solid. Compound wt: 107g Yield: 75%.[00294] MS (ES-): 195 (M-I). NMR (1H, CDCl3): 6.6 (IH, s, CH); 4.3 (2H, q, OCH2); 1.2 (12H, m, 4xCH3). M.Pt: 138-139C. |
| 75% |
With hydrazine; In ethanol; at 0 - 20℃; for 3h; |
To a solution of methyl 5,5-dimethyl-2,4-dioxohexanoic acid ethyl ester (720 mmol) in ethanol (500 muL) was added dropwise, at 0 C., hydrazine hydrate (640 mmol) and stirred for 3 h at room temperature. On completion of the reaction, the mixture was diluted with water (1 L) and stirred for 10 min. The precipitate was collected by filtration and dried at room temperature for 5 hours. The product was isolated as an off-white solid. Compound wt: 107 g Yield: 75%. MS (ES-): 195 (M-1). NMR (1H, CDCl3): 6.6 (1H, s, CH); 4.3 (2H, q, OCH2); 1.2 (12H, m, 4*CH3). M.Pt.: 138-139 C. |
- 3
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[ 10226-29-6 ]
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[ 83405-70-3 ]
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ethyl 3-(tert-butyl)-1-(5-oxohexyl)-1H-pyrazole-5-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 169 mg |
With caesium carbonate; In acetonitrile; for 2h;Reflux; |
3-tert-Butyl-1H-pyrazole-5-carboxylic acid ethyl ester (115 mg, 0.60 mmol) and <strong>[10226-29-6]6-bromo-2-hexanone</strong> (107 mg, 0.60 mmol) were dissolved in acetonitrile (5 ml).Add cesium carbonate (391 mg, 1.20 mmol),The mixture was heated under reflux for two hours.After the reaction is completed, the solvent is evaporated to dryness.Ethyl acetate,Water and saturated brine extract,The organic phase was combined, dried over anhydrous sodium sulfate, filtered and evaporated to dryness.Ethyl 3-(tert-butyl)-1-(5-oxohexyl)-1H-pyrazole-5-carboxylate (169 mg, 0.57 mmol). |
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