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CAS No. : | 10523-68-9 | MDL No. : | MFCD00074743 |
Formula : | C10H18ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WLDWDRZITJEWRJ-UHFFFAOYSA-N |
M.W : | 187.71 | Pubchem ID : | 25331 |
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: |
* 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 |
---|---|---|
30% | With sodium hydroxide; In 1,4-dioxane; water; at 80℃; for 5h; | Preparation of 3-(2-adamantylamino)-2-hydroxy-1-propanesulfonic acid (Compound KJ); To an 80 C. solution of 2-adamantanamine hydrochloride (2.50 g, 13.3 mmol) and sodium hydroxide (586 mg, 14.6 mmol) in 1,4-dioxane (7 mL) and water (7 mL) was added via syringe pump (1 hour addition) a solution of 3-chloro-2-hydroxy-propane sulfonic acid, sodium salt (1.76 g, 8.9 mmol) in 1,4-dioxane (1 mL) and water (9 mL). The solution was stirred at 80 C. for an additional 4 hours. The reaction was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid was suspended in EtOH (25 mL). The mixture was heated to reflux for 1 minute. The solid was removed by filtration. The pure product crystallized in the filtrate. The product was filtered, washed with EtOH (1×10 mL) and dried in vacuo. Yield: 30%. 1H NMR (D2O, 500 MHz) delta ppm 4.30 (m, 1H), 3.35 (m, 2H), 3.03 (m, 3H), 2.07 (m, 2H), 1.84 (m, 2H), 1.75 (m, 4H), 1.65 (d, 6H). 13C (D2O, 125 MHz) delta ppm 63.31, 55.03, 49.51, 36.51, 36.33, 36.26, 29.78, 29.23, 28.81, 26.63, 26.38. ES-MS 289 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -10 - 0℃; | N-adamantan-2-yl-2,4-dichloropyrimidine-5-carboxamide A suspension of 2-adamantanamine hydrochloride (1.776 g, 9.46 mmol) and N-ethyldiisopropylamine (3.27 mL, 18.92 mmol) in THF (10.00 mL) was added dropwise to a stirred solution of <strong>[2972-52-3]2,4-dichloropyrimidine-5-carbonyl chloride</strong> (2.00 g, 9.46 mmol) in dichloromethane (20 mL) at -10 C. under an atmosphere of nitrogen. The resulting solution was stirred at 0 C. for 1 hour. The reaction mixture was diluted with DCM (100 mL) and washed sequentially with 0.1M HCl (25 mL), saturated NaHCO3 (25 mL) and saturated brine (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude solid was triturated with isohexane to give a solid which was collected by filtration and dried under vacuum to give N-adamantan-2-yl-2,4-dichloropyrimidine-5-carboxamide (2.50 g, 81%) as a yellow powder. 1H NMR (400.13 MHz, DMSO-d6) δ 1.53 (2H, d), 1.71 (2H, s), 1.81 (5H, d), 1.85 (1H, s), 1.94-1.96 (3H, m), 2.00 (1H, s), 4.02-4.04 (1H, m), 8.56 (1H, d), 8.84-8.86 (1H, m) m/z (ESI+) (M+H)+=326; HPLC tR=2.65 min. |
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