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CAS No. : | 146651-75-4 | MDL No. : | MFCD02169707 |
Formula : | C11H16N2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | KCZFBLNQOSFGSH-UHFFFAOYSA-N |
M.W : | 208.26 | Pubchem ID : | 676311 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280 | UN#: | |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
67% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In water; N,N-dimethyl-formamide; | Reference Example 11 N-(2-t-Butoxycarbonylaminophenyl)-<strong>[775545-30-7]6-hydroxymethylpyridine-3-carboxylic acid</strong> amide (Reference Compound No.11-1) 2-Aminophenyl carbamic acid t-butyl ester (Reference Compound No.1-1, 0.60 g, 2.9 mmol), N,N-diisopropylethylamine (1.5 mL, 8.6 mmol), and HATU (1.1 g, 2.9 mmol) were added to a suspension of <strong>[775545-30-7]6-hydroxymethylpyridine-3-carboxylic acid</strong> (Reference Compound No. 10-1) in DMF (10 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (200 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL, 50 mL), and then the organic layer was washed with brine (100 mL) twice. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 0.66 g of the title reference compound as a brown oil. (Yield 67% in 2 steps) |
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h; | 2-Aminophenyl carbamic acid t-butyl ester (Reference Compound No.1-1, 0.60 g, 2.9 mmol), N,N-diisopropylethylamine (1.5 mL, 8.6 mmol), and HATU (1.1 g, 2.9 mmol) were added to a suspension of <strong>[775545-30-7]6-hydroxymethylpyridine-3-carboxylic acid</strong> (Reference Compound No.10-1) in DMF (10 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (200 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL, 50 mL), and then the organic layer was washed with brine (100 mL) twice. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 0.66 g of the title reference compound as a brown oil. (Yield 67% in 2 steps) [Show Image] 1H-NMR (400 MHz, DMSO-d6) delta 1.44 (s, 9H), 4.65 (d, J = 5.9 Hz, 2H), 5.59 (t, J = 5.9 Hz, 1H), 7.14 (td, J = 7.7, 1.5 Hz, 1H), 7.21 (td, J = 7.7, 1.5 Hz, 1H), 7.52 (dd, J = 7.7, 1.5 Hz, 1H), 7.59 (dd, J = 7.7, 1.5 Hz, 1H), 7.63 (d, J = 8.3 Hz, 1H), 8.31 (dd, J = 8.3, 2.1 Hz, 1H), 8.69 (s, 1H), 9.03 (d, J = 2.1 Hz, 1H), 9.94 (s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In dichloromethane; at 120℃; for 0.25h;Microwave irradiation; | General procedure: One millimolar of each diamine, glyoxaldehyde and boronic acid were taken into a microwave vial already equipped with a magnetic bar. 1 mL of dichloromethane was added to the system followed by heating it at 120 C for 15 min. The crude Petasis product was then directly loaded to an ISCO purification system and using ethylacetate/hexane as eluent (0-100% gradient over 25 min) the products were purified. A weighed out amount of Petasis product (0.10-0. 30 mmol) was then subjected to 1-2 mL of 20% TFA in dichloromethane. The reaction was stirred for 18 h at room temperature, evaporated in vacuo and crude material purified via chromatography (ISCO) to afford the desired product (77% yield) as a white solid. |
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