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With hydrogenchloride; In acetonitrile; for 1h;Heating / reflux;Product distribution / selectivity;
The 4- (3-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinazoline starting material used above was prepared as follows: 6-Acetoxy-4-chloro-7-methoxyquinazoline (Example 25-5 in W001/66099 ; 10. 0g, 39.6 mmole) was suspended in acetonitrile (400 ml) and 3-chloro-2-fluoroaniline (6. 05g, 41. 6 mmole) and hydrogen chloride (4. 0M solution in 1,4-dioxane) (10.4 ml, 41.6 mmole) were added. The reaction mixture was refluxed for one hour and then allowed to cool to ambient temperature. The resulting precipitate was filtered off, washed with acetonitrile and diethylether to give a white solid. This solid was added in portions to a stirred 7N methanolic ammonia solution (400 ml). The mixture was stirred for two hours and the precipitate filtered, washed with acetonitrile followed by diethylether and dried under vacuum to give 4- (3-chloro- 2-fluoroanilino) -6-hydroxy-7-methoxyquinazoline as a white solid (12. 1g, 95%) ; lH NMR Spectrum: (DMSOd6) 3.95 (s, 3H) ; 7.18 (s, lH) ; 7.20-7. 25 (m, 1H); 7.39-7. 44 (m, lH) ; 7.47- 7.52 (m, 11-1) ; 7.65 (s, lH) ; 8.31 (s, 1H) ; 9.45 (br. s, lH) ; Mass Spectrum: (M+H) + 320.
N-(3-chloro-2-fluorophenyl)-6-iodoquinazolin-4-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
In isopropyl alcohol; at 80℃; for 2h;
General procedure: To a solution of compound 12 (5.8 g, 20 mmol) in i-PrOH was added anilines (22 mmol) at room temperature (RT). Then the reaction mixture was heated to 80 C for 2 h. After the start material was completed, the mixture was filtered through celite, and the cake was washed by i-PrOH, then dried to obtain the desired compound 13a-f.
N-(3-chloro-2-fluorophenyl)-7-methoxy-6-nitroquinazolin-4-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
With acetic acid; triethylamine; for 48h;
A mixture of <strong>[55496-69-0]4-chloro-7-methoxy-6-nitroquinazoline</strong> 12a(2g, 8.35mmol, prepared according to literature 102008033749) And 3-chloro-2-fluoroaniline 13a (1.22g, 8.35mmol) were dissolved in 80ml acetic acid and triethylamine (1.868, 18.37 mmol)Stirring reaction for 48 hours, a large number of solid precipitation.The reaction solution was poured into 250 mL of water, stirred for 0.5 hour, filtered,The filter cake was dried in vacuo to give the title product (3-chloro-2-fluorophenyl) -7-methoxy-6-nitroquinazolin-4-amine 13b (2.738, pale yellow solid), yield: 94%.
In N,N-dimethyl-formamide; at 120 - 130℃;Inert atmosphere;
General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5?1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120?130 °C until the aniline was fully consumed (3?14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1?2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.
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