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CAS No. : | 6345-27-3 | MDL No. : | MFCD00040385 |
Formula : | C6H8ClN3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | IONKMFGAXKCLMI-UHFFFAOYSA-N |
M.W : | 157.60 | Pubchem ID : | 2776844 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
15% | With sodium ethanolate; In ethanol; for 6h;Heating / reflux; | At room temperature, sodium ethoxide (590 mg) was dissolved in anhydrous ethanol (50 ml). 4-Amidinopyridine hydrochloride (1.31 g) was added to the resulting solution. After an anhydrous ethanol solution (ethanol: 50 ml) of ethyl 2,2-diformylacetate (1.20 g) was added dropwise, the resulting mixture was heated under reflux for 6 hours. Dichloromethane and water were added to the residue obtained by distilling off the solvent under reduced pressure. The organic layer thus separated was dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, the residue was crystallized in ethanol, whereby the title compound (279 mg, 15percent) was obtained as colorless crystals.1H-NMR (DMSO-d6) delta: 1.46(3H,t,J=7.3Hz), 4.48 (2H, q, J=7.3Hz), 8.35 (2H, d, J=5.9Hz), 8.82(2H,d,J=5.9Hz), 9.38(2H,s). MS (FAB)m/z: 230(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With sodium ethanolate; In ethanol; dichloromethane; water; | [Referential Example 142] Ethyl-2-(4-pyridyl)-5-pyrimidinecarboxylic acid Sodium ethoxide (590 mg) was dissolved in anhydrous ethanol (50 ml) at room temperature. To the resulting solution, 4-amidinopyridine hydrochloride (1.31 g) was added, followed by the dropwise addition of a solution of ethyl 2,2-diformylacetate (1.20 g) in anhydrous ethanol (50 ml). The resulting mixture was heated under reflux for 6 hours. To the residue obtained by distilling off the solvent under reduced pressure, dichloromethane and water were added. The organic layer thus separated was dried over anhydrous sodium sulfate. After the solvent wasconcentrated under reduced pressure, the residue was crystallized in ethanol, whereby the title compound (279 mg, 15percent) was obtained as colorless crystals. 1H-NMR (DMSO-d6) delta: 1.46(3H,t,J=7.3Hz), 4.48(2H,q,J=7.3Hz), 8.35(2H,d,J=5.9Hz), 8.82(2H,d,J=5.9Hz), 9.38(2H,s). MS (FAB) m/z: 230 (M+H)+. Elementary analysis for C12H11N3O2 Calculated: C, 62.87; H, 4.84; N, 18.33. Found: C, 62.80; H, 4.78; N, 18.25. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Example A6; a) Preparation of intermediate 11; Tetrahydro-S-oxo^-thiophenecarboxylic acid, methyl ester (0.006 mol) was added drop wise to a solution of 4-pyridinecarboximidamide, monohydrochloride (0.006 mol) and K2CO3 (0.006 mol) in H2O (100 ml). The reaction mixture was stirred for one hour at 60 0C. The mixture was treated with 1 N HCl to get a neutral pH. The resulting precipitate was filtered off and dried. Yield: 1.2 g of intermediate 11 (85 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.359 g | Synthesis of 3,5-Dichloro-N-(imino-pyridin-4-yl-methyl)-isonicotinamide [A060] 3,5-Dichloro-isonicotinic acid (10.4mmol, 1.997g), was dissolved in anhydrous DMF (50mL) at room temperature and HATU (10.4mmol, 3.95g), added in one portion and the mixture stirred for 5mins. Then DIPEA (28.6mmol, 5.0mL) was added in one portion and reaction stirred for 40 minutes. Pyridine-4-carboximidamide hydrochloride (9.52mmol, 1.5g) was added in one portion and reaction stirred at room temperature for 18 hours. The reaction mixture was then poured into water (~250mL in total including rinses of reaction vessel) in a conical flask. The resultant mixture was stirred at room temperature for 90 minutes and the precipitate formed was filtered, washed with water (x2) and ether (x2). Then the solid was dried in vac oven for 4hrs to yield the title compound [A060] (2.359g), as a pale brown powder. LCMS method: 1, RT:3.31 min, MI 295 [M+H]. | |
2.359 g | Synthesis of 3,5-Dichloro-N-(imino-pyridin-4-yl-methyl)-isonicotinamide [A060] (0145) 3,5-Dichloro-isonicotinic acid (10.4 mmol, 1.997 g), was dissolved in anhydrous DMF (50 mL) at room temperature and HATU (10.4 mmol, 3.95 g), added in one portion and the mixture stirred for 5 mins. Then DIPEA (28.6 mmol, 5.0 mL) was added in one portion and reaction stirred for 40 minutes. Pyridine-4-carboximidamide hydrochloride (9.52 mmol, 1.5 g) was added in one portion and reaction stirred at room temperature for 18 hours. (0146) The reaction mixture was then poured into water (250 mL in total including rinses of reaction vessel) in a conical flask. The resultant mixture was stirred at room temperature for 90 minutes and the precipitate formed was filtered, washed with water (×2) and ether (×2). Then the solid was dried in vac oven for 4 hrs to yield the title compound [A060] (2.359 g), as a pale brown powder. LCMS method: 1, RT:3.31 min, MI 295 [M+H]. |
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