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CAS No. : | 98556-31-1 | MDL No. : | MFCD01862193 |
Formula : | C8H4ClIN2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BDAIUOPDSRAOKI-UHFFFAOYSA-N |
M.W : | 290.49 | Pubchem ID : | 11173809 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
76% | In isopropyl alcohol; for 3.5h;Reflux; | 6-Iodo-(4-benzyloxy-3-trifluoromethyl-phenyl)-quinazolin-4-yl)amine (0648) The mixture of 4-chloro-6-iodo-quinazoline (366 mg, 1.26 mmol) and 4-O-benzyl-3-trifluoroaniline (405 mg, 1.26 mmol) in isopropanol (12 ml) was heated to reflux for 3.5 hours. Filtered, washed with isopropanol and dried. 535 mg yellow solid was afforded. (yield: 76%). ESI-MS m/z 522 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage 1: Preparation of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6- iodo-4-quinazolinamine 4-Chloro-6-iodoquinazoline (1wt) was added to a solution of fluorobenzyloxyaniline (0.894wt, 1.03equiv) in N-methylpyrrolidinone (8.26wt, 8vol) at ca 20C, and after the initial exotherm had subsided, the resulting solution was stirred at 20-25C for at least 30 minutes. The dark solution was treated with triethylamine (0.58vol, 1.2equiv) and the mixture was stirred for 20-30 minutes. Isopropanol (2.5vol) was added and the mixture was heated to ca 50C. Water (up to 3vol) was added slowly to the vessel over 10-15 minutes, while keeping the temperature at ca 50C. Once crystallisation had commenced the addition was stopped and the resulting slurry was aged for 30-45 minutes at ca 50C. Any residual water (from the 3vol) was added, then further water (5vol) was added to the vessel over ca 30 minutes while maintaining the temperature at ca 50C. The resulting slurry was cooled to ca 20C over ca 30 minutes and aged at ca 20C for at least 30 minutes. The solid was collected by filtration and washed sequentially with water (2 x 5vol), then isopropanol (5vol). The product was dried in vacuo at ca 60C to give the title compound as a cream crystalline solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In isopropyl alcohol; at 20℃; for 0.5h; | To a solution of 4-chloro-6-iodoquinazoline (2.60 g, 8.95 mmol) in isopropanol (60 mL) was added <strong>[1123-93-9]1,3-benzothiazol-5-amine</strong> (1.479 g, 9.85 mmol). The mixture was then placed in oil bath10 preheated to 90°C. The reaction was complete in 30 min., and the solution was allowed tocool to room temperature. A yellow solid precipitated and was filtered and dried toprovide 3.6 g (91 percent) of the title compound. |
91% | In isopropyl alcohol; at 90℃; for 0.5h; | N-1,3-benzothiazol-5-yl-6-iodo-4-quinazolinamine To a solution of 4-chloro-6-iodoquinazoline (2.60 g, 8.95 mmol) in isopropanol (60 mL) was added <strong>[1123-93-9]1,3-benzothiazol-5-amine</strong> (1.479 g, 9.85 mmol). The mixture was then placed in oil bath preheated to 90°C. The reaction was complete in 30 min., and the solution was allowed to cool to room temperature. A yellow solid precipitated and was filtered and dried to provide 3.6 g (91 percent) of the title compound. The following intermediate, N-(5-fluoro-1H-indazol-3-yl)-6-iodo-4-quinazolinamine, was made in the same manner: |
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