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CAS No. : | 740081-22-5 | MDL No. : | MFCD26395271 |
Formula : | C17H13ClFN3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YJNQYSVKLRFVQN-UHFFFAOYSA-N |
M.W : | 361.75 | Pubchem ID : | 57476867 |
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: |
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* 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 |
---|---|---|
100% | With ammonia methyl alcohol; In methanol; at 20℃; for 2h; | Taking compound 3 (200 mg) dissolved in methanol (2 ml) in, adding methanol and ammonia solution (7 N, 1 ml), then stirred at room temperature 2 hours; the reaction the fluid turns on lathe job to the compound 1 (white powder, 176 mg, quant.). |
83% | With ammonia; N,N-diethylaniline; In methanol; at 20℃; for 18h; | To a stirred solution of compound 6 (2.30 g, 5.79 mmol) in MeOH (50 mL) was added concentrated ammonia (4.0 mL). The reaction mixture was stirred at rt for 18 h. The resultant precipitate was filtered, and washed with MeOH to afford 7 (1.54 g, 83%) as a pale yellow solid, mp 280-282 C. 1H NMR (DMSO-d6): d 9.75 (s, 1H), 9.48 (s, 1H), 8.35 (s, 1H), 7.66 (s, 1H), 7.52 (t, J = 6.5 Hz, 1H), 7.45 (t,J = 7.0 Hz, 1H), 7.26 (t, J = 8.0 Hz, 1H), 7.21 (s, 1H), 3.98 (s, 3H). |
81% | With ammonia; In methanol; for 2h;Sealed tube; Inert atmosphere; Heating; | To JGK018 (550 mg, 1.520 mmol) was dropwise added ammonia solution (8.0 mL, 7 N in methanol). After being heated at 50 C (bath temperature) in sealed tube with stirring for 2 h, the reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting white solid were washed successively with Et20 (2 x 50 mL) and collected to give 13 (394 mg, 81%); The resulting spectroscopic data was matched with that of Zhang, X. et al. Med. Chem. 2015, 58, 8200-8215. |
77% | With ammonia; In methanol; water; at 50℃; for 2h; | 6-ACETOXY-4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXYQUINAZOLINE HYDROCHLORIDE FROM step 1 (8.72 g, 21.9 mmol) was dissolved in methanol (200 ml). Concentrated aqueous ammonia (15 ml) was added, and the solution heated to 50C with stirring for 2 hours, causing precipitation of a cream coloured solid. The solid was collected by filtration, washed with diethyl ether (3x 200 ml), and dried in vacuo at 60C over diphosphorous pentoxide, giving the product as an off white solid (5.40 g, 77%); H NMR : 3.95 (s, 3H), 7.19 (s, 1H), 7.23 (dd, 1H), 7.42 (dd, 1H), 7.50 (dd, 1H), 7.64 (s, 1H), 8.32 (s, 1H), 9.43 (s, 1H), 9.67 (br. s, 1H) ; Mass Spectrum: 320.4, 322.4. |
77% | With ammonia; In water; at 50℃; for 2h; | 6-ACETOXY-4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXYQUINAZOLINE hydrochloride from step 1 (8.72 g, 21.9 mmol) was dissolved in methanol (200 ml). Concentrated aqueous ammonia (15 ml) was added, and the solution heated to 50C with stirring for 2 hours, causing precipitation of a cream coloured solid. The solid was collected by filtration, washed with diethyl ether (3x 200 ml), and dried in vacuo at 60C over diphosphorous pentoxide, giving the product as an off white solid (5.40 g, 77%). 1H NMR : 3.95 (s, 3H), 7.19 (s, 1H), 7.23 (dd, 1H), 7.42 (dd, 1H), 7.50 (dd, 1H), 7.64 (s, 1H), 8.32 (s, 1H), 9.43 (s, 1H), 9.67 (br. s, 1H); Mass Spectrum : 320.4, 322.4. |
With methanol; potassium carbonate; at 20℃; | Intermediate 74-[(3-Chloro- -fluorophenyl)aminol-7-methoxyquinazolin-6-olTo a solution of Intermediate 6 (181 g, 0.396 mol) in MeOH (2 L) was added potassium carbonate (138 g, 1 mol) and the reaction mixture was stirred at RT overnight. The reaction mixture was filtered and the solid washed with MeOH. The filtrate was concentrated in vacuo to afford Intermediate 7 (280 g, 60% purity, contained potassium carbonate). 1H NMR (DMSO-d6400MHz): delta 8.01 (s, 1H), 7.61-7.58 (m, 1H), 7.27-7.24 (m, 1H), 7.17-7.13 (m, 1H), 6.95 (s, 1H), 6.83 (s, 1H), 3.79 (s, 3H). | |
With potassium carbonate; In methanol; at 20℃; | To a solution of Intermediate 6 (181 g, 0.396 mol) in MeOH (2 L) was added potassium carbonate (138 g, 1 mol) and the reaction mixture was stirred at RT overnight. The reaction mixture was filtered and the solid washed with MeOH. The filtrate was concentrated in vacuo to afford Intermediate 7 (280 g, 60% purity, contained potassium carbonate). 1H NMR (DMSO-d6 400 MHz): delta 8.01 (s, 1H), 7.61-7.58 (m, 1H), 7.27-7.24 (m, 1H), 7.17-7.13 (m, 1H), 6.95 (s, 1H), 6.83 (s, 1H), 3.79 (s, 3H). | |
30 g | With methanol; ammonium hydroxide; at 20 - 30℃; for 6h; | 35g of compound 4,100g ammonia water,70g of methanol was added to the reaction flask,At a reaction temperature of 20-30 C,Stir for 6h,After TLC detection reaction is complete, suction filtration, and then dried at 40 ~ 50 C, to obtain 30g of compound 5; |
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