* 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.
With hydrogen;palladium on activated charcoal; In tetrahydrofuran; for 16.0h;
Step D; Preparation of [1,2,4]triazolo[1,5-a]pyridin-7-ol: A 250 mL, single-neck, round-bottomed flask was charged with 7-(benzyloxy)-[1,2,4]triazolo[1,5-a]pyridine (3.20 g, 14.2 mmol), Pd/C (0.756 g, 0.710 mmol), and THF (125 mL). The reaction was stirred under an atmosphere of hydrogen for 16 hours, then filtered (GF paper) and concentrated to a white solid. The solids were titrated with EtOAc and collected by filtration to provide the desired product.
tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 12.0h;
Step F: Preparation of tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate: A vial charged with tert-butyl 3-chloro-2,4-difluorobenzoate (0.210 g, 0.845 mmol), <strong>[1033810-70-6][1,2,4]triazolo[1,5-a]pyridin-7-ol</strong> (0.114 g, 0.845 mmol), cesium carbonate (0.413 g, 1.27 mmol), and DMF (1.7 ml). The reaction was heated to 80 C for 12 hours, then poured into ice water. The resulting solids were collected by filtration and purified by flash chromatography, eluting with gradient of 10% EtOAc/ Hexanes to 50% EtOAc/Hexanes to provide the desired product.
(S)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoropiperidin-4-yl)oxy)-7-methoxyquinazolin-4-amine hydrogen chloride salt[ No CAS ]
N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-(((1R,5S)-8-(2,2-difluoroethyl)-8-azabicyclo[3.2.1]octan-3-yl)oxy)quinazolin-4-amine[ No CAS ]
(±)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-(((2R,4S)-1-(methyl-d3)-2-(trifluoromethyl)piperidin-4-yl)oxy)quinazolin-4-amine[ No CAS ]
(±)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-(methyl-d3)piperidin-4-yl)oxy)-6-(methoxy-d3)quinazolin-4-amine[ No CAS ]
(±)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-methylpiperidin-4-yl-4-d)oxy)-7-methoxyquinazolin-4-amine[ No CAS ]
(R)-N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-5-((4,4-difluoro-1-methylpiperidin-2-yl)methoxy)-6-methoxyquinazolin-4-amine[ No CAS ]
With caesium carbonate; In dimethyl sulfoxide; at 80.0℃; for 3.0h;
The mixture of l-fluoro-2-methyl-4-nitrobenzene (96 mg, 0.617 mmol), [l,2,4]triazolo[l,5-a]pyridin-7-ol (100 mg, 0.740 mmol) aid cesium carbonate (482 mg, 1.48 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80 C for 3 hr. The resulting mixture was poured into ice water and the precipitate was filtered and dried using blowing nitrogen gas to give 4-([l,2,4]triazolo[l,5-a]pyridin-7-yloxy)-3-methylaniline as a brown solid (145 mg, 87 %).
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -5 - 50℃; for 2h;
1-3 Example 1Synthesis of compounds represented by formula 3
To the stirred THF (500 mL) was added the compound represented by formula 1 (13.51 g, 100 mmol), the compound represented by formula 2 (12.93 g, 105 mmol) and PPh3 (31.48 g, 120 mmol), and kept at -5 ~ 5 , slowly add diethyl azodicarboxylate (DEAD) (62.70 g, 360 mmol) dropwise, slowly heat up to about 50 ° C and stir for 2 h. After the reaction is completed, spin the reaction solution under reduced pressure, add CH2Cl2 (250 mL) to dissolve and filter , the organic layer was washed with brine (200 mL) and then concentrated, purified with a silica gel column (the elution solvent was a mixed solvent of petroleum ether/ethyl acetate with a volume ratio of 10:1), and the eluent was concentrated to dryness to obtain formula 3 The compound shown, the yield was 21.36 g, and the yield was 88.9%.
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