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CAS No. : | 55314-16-4 | MDL No. : | MFCD00115180 |
Formula : | C10H12N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MZLRFUCMBQWLNV-FNORWQNLSA-N |
M.W : | 176.22 | Pubchem ID : | 5369165 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
1- (3-Pyridyl)-3- (dimethylamino)-2-propen-1-one (CAS: 55314-16-4) can be used in the preparation of Nilotinib (AMN-107) (CAS: 641571-10-0). Nilotinib, also known as AMN107, is a tyrosine kinase inhibitor.
* 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 |
---|---|---|
With sodium acetate; In hexane; acetic acid; | EXAMPLE 1 5-(3-Pyridyl)imidazo[1,2-a]pyrimidine A mixture of 5.29 g of <strong>[1450-93-7]2-aminoimidazole hemisulfate</strong>, 3.28 g of anhydrous sodium acetate and 7.04 g of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (prepared according to the procedure of Example 1 in U.S. Pat. No. 4,281,000) in 100 ml of glacial acetic acid was heated under reflux for 16 hours. The solvent was removed in vacuo. The solid residue was made basic with saturated aqueous sodium bicarbonate, then was extracted with dichloromethane. The dichloromethane solution was passed through a short column of a hydrous magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization was noted. On cooling, the desired compound was separated and collected by filtration and gave 2.54 g of yellow prisms, mp 162°-164° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium hydroxide; In butan-1-ol; at 120℃; for 2h; | NaOH (0.78 g, 19.5 mmol) was added to a mixture of 3-(dimethylamino)-l-(pyridin-3- yl)prop-2-en-l-one (3.52 g, 20.0 mmol) and guanidine carbonate (1.80 g) in n-butanol (20 mL). The mixture was heated at 1200C for 2 h. After cooling, the precipitates formed was collected by filtration and dried under vacuum to afford the desired product (2.3g, 66percent). LCMS: (M+H)+= 173.2. |
In iso-butanol; for 24h;Heating / reflux; | 4-Pyridin-3 - yl-pyrimidin-2- ylamine (7)[0042] A mixture of 3-acetylpyridine (20.72 g, 171.0 mmol) and N, N-dimethylformamide dimethyl acetal (60 mL, 450 mmol) is heated at 110 0C. After reaction overnight, the reaction mixture is cooled to room temperature and concentrated. Ethyl ether (20 mL) and hexanes (60 <n="17"/>P A T E N TGNF Docket No.: P1286PC10mL) are added to the residue. The resulting solid is collected by filtration, washed with hexanes, and dried to afford 3-dimethylamino-l-pyridin-3-yl-propenone which is used for next reaction without further purification. A mixture of 3-dimethylamino-l-pyridin-3-yl-propenone (17.6 g, 100 mmol) and guanidine carbonate (10.8 g, 60.0 mmol) in 2-butanol (100 mL) is heated at reflux. After 24 hours, the reaction mixture is cooled to room temperature and concentrated. The residue is triturated in water (50 mL). The solid is collected by filtration, washed with water and dried to afford the desired product 4-pyridin-3-yl-pyrimidin-2-ylamine as a white solid. C29H31N7O Exact MS: 172.07. Found MS m/z 173.1 (M+l). 1H NMR (DMSO-J6): delta 9.23 (s, IH), 8.69 (m, IH), 8.37 (m, 2H), 7.54 (d, IH), 7.20 (d, IH), 6.80 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide; In tert-butyl alcohol; at 85℃; | The starting material was added 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (Compound 4) (1.76 g, 0.01 mol) in a three-neck flask.Guanidine hydrochloride (2.87 g, 0.03 mol)And sodium hydroxide (1.2g, 0.03mol), add 25ml of solvent t-butanol, stir, heated in a constant temperature oil bath to 85 C reflux reaction, 6-8h. After the reaction is completed, the solvent is spin-dried, an appropriate amount of water and ethyl acetate are added, the insoluble solid is filtered, and the filter cake is washed with water and dried to obtain a yellow solid; the filtrate is further subjected to extraction, the organic phase is collected, dried, and the solvent is dried and dried. The solid was subjected to column chromatography to give a pale yellow solid, Compound 5 (1.55 g, yield: 90%). |
With sodium hydroxide; In butan-1-ol; at 120℃; | To aflask 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one(1.76 g, 10.0 mmol), guanidine hydrochloride (1.15 g, 12.0 mmol), NaOH (480 mg,12.0 mmol) and n-BuOH (20 mL) were added. The mixturewas heated to 120 oC.The resulting solid was collected, rinsed with water (50 mL) and dried overhigh vacuum to get the product as light yellow crystalline (1.51 g, 88% yield).1H NMR(400 MHz, DMSO) delta 9.23 (d, J = 2.0 Hz, 1H), 8.67 (dd, J = 4.7,1.3 Hz, 1H), 8.38 (dt, J = 8.0, 1.8 Hz, 1H), 8.36 (d, J = 5.1 Hz,1H), 7.52 (dd, J = 8.0, 4.8 Hz, 1H), 7.20 (d, J = 5.1 Hz, 1H),6.81 (s, 2H).13C NMR (101 MHz, DMSO) delta163.78, 161.53, 159.36, 151.11, 147.93, 134.11, 132.44, 123.72, 105.99 | |
With sodium hydroxide; In butan-1-ol; at 120℃; | 3-dimethylamino-1-(3-pyridyl)-2-propenyl-1-one (1.76 g, 10.0 mmol) was suspended in n-butanol (20 mL), followed by the addition of guanidine hydrochloride (1.15 g, 12.0 mmol) and NaOH (480 mg, 12.0 mmol). The mixture was heated to 120 C for reacting overnight. The precipitated solid was collected and washed with water (50 mL), followed by vacuum drying to give a light yellow crystal (1.51g, 88% yield). 1H NMR (400 MHz, DMSO) delta 9.23 (d, J = 2.0 Hz, 1H), 8.67 (dd, J = 4.7, 1.3 Hz, 1H), 8.38 (dt, J = 8.0, 1.8 Hz, 1H),8.36 (d, J = 5.1 Hz, 1H), 7.52 (dd, J = 8.0, 4.8 Hz, 1H), 7.20 (d, J = 5.1 Hz, 1H), 6.81 (s, 2H). 13C NMR (101 MHz, DMSO) delta 163.78, 161.53, 159.36, 151.11, 147.93, 134.11, 132.44, 123.72, 105.99 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; In butan-1-ol; for 16h;Reflux; | 3-(Dimethylamino)-1-(pyridine-3-yl) prop-2-en-1-one (15.4 g, 0.088 mol), guanidine nitrate (10.7 g, 0.088 mol), and sodium hydroxide (3.5 g, 0.088 mol) were dissolved in n-butanol (120 mL). The mixture was heated to reflux with stirring and maintained for 16 hours. The reaction mixture was then cooled to room temperature. The solid was collected and washed with water (400 mL). The desired product was dried under vacuum for three days and 12.7 g of yellow crystals of desired product was obtained (yield: 85percent); 1H NMR (500 MHz, CDCl3) delta 5.15 (br., 2H), 7.09 (d, 1H), 7.44 (in, 1H), 8.33 (d, 1H), 8.42 (d, 1H), 8.73 (d, 1H), 9.22 (s, 1H). LC-MS (m/z) calculated, 172.2, found 173.2 [M+H]+. |
1.18 g | With sodium hydroxide; In butan-1-ol; at 90℃; for 0.333333h;Microwave irradiation; | The obtained compound 3 followed by 3-(dimethylamino)-1-(pyridin-3-yl) prop-2-en-1-one (0.1 mol), guanidine nitrate(0.1 mol), sodium hydroxide (0.1 mol), and n-butanol (12.5 mL) was irradiated in the microwave synthesizer at 90 C for 20 min. Aftercompletion of the reaction mixture poured into ice-cold water andthe resulting solid was filtered and washed with water. The obtainedsolid of compound 4 (1.18 g) was dried under vacuum.Melting point 190-192 °C, ES-MS (M1) found (m/z): 173.1. |
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