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CAS No. : | 685115-77-9 | MDL No. : | MFCD04110274 |
Formula : | C11H13Cl2N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BJCHGDBASIDUOJ-UHFFFAOYSA-N |
M.W : | 274.15 | Pubchem ID : | 2811640 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 150℃; for 0.75h;Microwave irradiation; | To a mixture of <strong>[685115-77-9]1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide</strong> 23 (24 mg, 0.088 mmol), 3,4-diimethoxyphenyllboronic acid (19 mg, 0.11 mmol), and tetrakis (triphenylphosphine)palladium(O) (5 mg, 5 mol%) in acetonitrile (1 ml.) was added a 0.5 M aqueous solution of sodium carbonate (0.25 ml_, 0.12 mmol). The mixture was heated at 150 0C in a microwave reactor for 45 min, then cooled to r.t. and purified on an SCX-2 cartridge (MeOH followed by 0.5 M NH3 in MeOH). The crude product was purified by preparative tic on silica gel (CH2CI2, MeOH, 10:1 ) to give impure title compound (7 mg). Further purification by preparative hplc (H2O, MeCN, 90:10-10:90, 30 min) furnished the title compound as a white solid, LC-MS (ESI, 3.5 min) R, 1.60 min, m/z 376 (100%, [M+H]+); mlz (ESI) C19H23CIN3O3 requires 376.1428 found [M+H]+ 376.1421. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With polyphosphoric acid; at 80 - 170℃; | To a solution of <strong>[685115-77-9]1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide</strong> 23 (0.10 g, 0.36 mmol) in polyphosphoric acid (5 ml.) at 80 0C was added vinylene carbonate (35 mg,0.40 mmol). The mixture was heated at 170 0C for 4 hours, cooled to r.t. and poured into water (200 ml_). The mixture was extracted with ethyl acetate (3 x 50 ml.) and the combined organic extracts were washed with water (100 ml_), a saturated solution of sodium hydrogen carbonate (50 ml_), water (50 ml_), brine (50 ml_), dried (MgSO4) and concentrated under reduced pressure to furnish a colourless oil (12 mg). The crude product was purified by preparative tic on silica gel (CH2CI2, MeOH, 10:1 then hexane,EtOAc, 1 :1 ) to furnish the title compound as a white solid (13 mg, 12%), LC-MS (ESI) Rt 2.66 min, m/z 298 (100%, M+); m/z (ESI) Ci3H14CI2N3O requires 298.0508 found [M+H]+ 298.0507. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 150℃; for 0.75h;Microwave irradiation; | To a suspension of <strong>[685115-77-9]1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide</strong> 23 (75 mg, 0.27 mmol), 1 ,5-dimethyl-4-pyrazole boronic acid pinacol ester (76 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (16 mg, 5mol%) in acetonitrile (3 ml.) was added 0.5 M solution of sodium carbonate (0.77 ml_, 0.38 mmol). The mixture was heated to in a microwave reactor at 150 0C for 45 min. Once cooled the reaction was concentrated in vacuo and dry loaded onto silica. The crude product was purified by flash column chromatography on silica gel (CH2CI2, EtOH, 97:3-80:20, biotage 25+S) to furnish the title compound as a clear colourless oil (24 mg, 26%), LC-MS (ESI, 4 min) Rt 1.49 min, m/z 334 (100%, [M+H]+); m/z (ESI) Ci6H20N5OCI requires 333.1356, found [M+H]+ 333.1354. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[685115-77-9]1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide</strong> 23 (30 mg, 0.1 1 mmol) in THF (2 ml_), at 0 0C, was added a 1 M solution of borane THF complex in THF (11.1 ml_, 1.1 mmol). The reaction was stirred for 1 hour before warming to r.t. and stirring for a further 18 hr. To the reaction was added 2M HCI (2ml), the mixture diluted with water (20 ml) and extracted with EtOAc (2 x 20 ml.) and the combined organic extracts were washed with brine (25 ml_). The combined aqueous extracts were basified with saturated sodium hydrogen carbonate and then extracted with EtOAc (2 x 20 ml_). The combined organic extracts were washed with brine (20 ml_), dried (MgSO4) and concentrated under reduced pressure to give a crude colourless oil (8 mg). The crude product was purified by flash column chromatography on silica gel (CH2CI2, MeOH, 97:3 to CH2CI2, 1 M methanolic NH3, 9:1 ) to furnish the title compound, LC-MS (ESI, 3.5 min) R, 1.45 min, m/z 260 (91 %, [M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With Lawessons reagent; In tetrahydrofuran; for 2.5h;Reflux; | To a solution of <strong>[685115-77-9]1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide</strong> 23 (40 mg, 0.15 mmol) in THF (2 mL) was added Lawesson's reagent (71 mg, 0.18 mmol) and the mixture was heated at reflux for 2.5 h. After cooling to r.t. the mixture was poured into a saturated solution of sodium hydrogen carbonate (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2Cb, MeOH, 99:1 ) to furnish the title compound as a white solid (21 mg, 40%), m/z (ESI) C11H14CI2N2S requires 290.0280 found [M+H]+ 290.0280. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With urea hydrogen peroxide adduct; trifluoroacetic anhydride; at 0 - 20℃; for 16.5h; | To a solution of <strong>[685115-77-9]1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide</strong> 23 (100 mg, 0.36 mmol) and hydrogen peroxide. urea complex (72 mg, 0.77 mmol) in CH2Cb (2 ml.) cooled to 0 0C was added trifluoroacetic anhydride (0.10 ml_, 0.73 mmol). After 30 min the solution was warmed to r.t, after a further 16 hours a saturated solution of Na2S2Os (10 ml.) was added. The mixture was extracted with CH2CI2 (2 x 20 ml_), the combined organic extracts were washed with a saturated solution of NaHCOs (20 ml_), brine (20 ml_), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2CI2/Me0H, 98:2) to furnish the title compound as a white solid (20 mg, 19%), m.p. 130-133 0C; umax (CHCI3)/ cm"1 3026. 2855, 1724, 1452, 1273, 1 107. |
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