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CAS No. : | 496-12-8 | MDL No. : | MFCD00605324 |
Formula : | C8H9N | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GWVMLCQWXVFZCN-UHFFFAOYSA-N |
M.W : | 119.16 | Pubchem ID : | 422478 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H227-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 |
---|---|---|
60% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; | (Intermediate Example 89) 3-Amino-1-(1,3-dihydroisoindol-2-yl)-3-methylbutan-1-one 2,3-Dihydro-1H-isoindole (543 mg) and <strong>[625-05-8]3-amino-3-methylbutanoic acid</strong> (700 mg) were dissolved in N,N-dimethylformamide (30 ml). N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (876 mg) and hydroxybenzotriazole (698 mg) were added thereto at 0°C, and then the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic phase was separated, and the aqueous phase was adjusted to pH 9 by adding a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure to give the title compound (0.60 g, Y.: 60percent) as a brown oily matter. 1H NMR; (CDCl3) delta (ppm): 1.2 (6H, s), 2.4 (2H, s), 4.7-4.8 (4H, m), 7.2-7.3 (4H, m). ESI/MS (m/z): 219 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; | Example 16 7-(2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid STR143 133 mg of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 83 mg of isoindoline, 152 mg of DBU, and 1.5 ml of anhydrous DMF were processed in the same manner as in Example 1 to produce 65 mg of the target compound. Melting Point: above 262°-267° C. (decomposed) 1 H-NMR (DMSO-d6) delta:8.63 (1H, s, C2 --H), 7.90 (1H, d, J=14HZ, C5 --H), 7.20-7.50 (5H, C8 --H, ARM-H), 5.10 (4H, s, 2 x --CH2 N--), 3.80 (1H, m, STR144 1.15-1.45 (4H, m, STR145 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine; In dichloromethane; at 20℃; for 1h; | A solution of 4-formylbenzene sulfonyl chloride (1) (0.50 g, 2.44 mmol) in dichloromethane (5 mL) was treated with isoindoline (0.32 g, 2.68 mmol) and triethylamine (0.41 mL, 2.93 mmol). The resultant mixture was stirred at room temperature for 1 h. A saturated aqueous solution of sodium bicarbonate (10 mL) was added. The product was extracted three times with 10 mL of dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated in vacuo. The crude material (0.67 g, 96% yield) was used in the next reaction without purification: Crude 1H NMR (400 MHz, CDCl3) delta 10.06 (s, IH), 8.05-8.00 (m, 4H), 7.25-7.20 (m, 2H), 7.20-7.14 (m, 2H), 4.66 (s, 4H); ESI+ MS: m/z (rel intensity) 288.0 (100, [M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 140℃; for 1h;Sealed tube; Microwave irradiation; | EXAMPLE 1096- [3 -(Isoindolin-2- ylmethvOphenyl] quinoxaline3-(Bromomethyl)phenylboronic acid (215 mg, 1.00 mmol), isoindoline (119 mg, 1.00 mmol), potassium phosphate (200 mg, 1.00 mmol) and DME (7 mL) were combined in a sealed tube and heated under microwave irradiation to 14O0C for 1 h. 6-Bromo- quinoxaline (209 mg, 1.00 mmol), water (2 mL) and Pd(PPh3)4 (115 mg, 0.10 mmol) were added to the reaction mixture, which was heated under microwave irradiation to 14O0C for a further 1 h. After cooling, the mixture was filtered through Celite. The filtrate was concentrated to dryness and purified by preparative HPLC to give the title compound (50.1 mg, 15%) as a brown solid. deltaH (DMS(W6) 9.02 (IH, d, J 1.85 Hz), 8.99 (IH, d, J 1.86 Hz), 8.40 (IH, d, J 2.01 Hz), 8.32-8.21 (2H, m), 7.93 (IH, s), 7.85 (IH, dt, J7.61, 1.57 Hz), 7.58 (IH, t, J 7.55 Hz), 7.52 (IH, d, J7.63 Hz), 7.28-7.19 (4H, m), 4.04 (2H, s), 3.95 (4H, s). LCMS (ES+) 338 (M+H)+, 3.85 minutes {Method 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In 1,4-dioxane; at 80℃; for 3h; | 2.1 Preparation of 4-(1,3-dihydroisoindol-2-yl)-6-iodoquinazoline 0.50 g of <strong>[98556-31-1]4-chloro-6-iodoquinazoline</strong>, 0.27 g of 2,3-dihydro-1H-isoindole, 0.42 ml of triethylamine in 4 ml of dioxane are heated at 80 C. in a flask until the quinazoline has reacted virtually completely (HPLC check, about 3 hours). The cooled reaction solution is evaporated to dryness in a rotary evaporator. The residue is suspended in EA. The undissolved solid is filtered off, rinsed with water and dried, giving 0.56 g of 4-(1,3-dihydroisoindol-2-yl)-6-iodoquinazoline as slightly yellowish solid (yield 93%, content 94%); MS-FAB (M+H+)=373.8; Rf (polar method): 1.73 min. This is employed for the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydride; In tetrahydrofuran; for 12h;Inert atmosphere; Reflux; | In this example, under the protection of nitrogen, A-7-1 (1.0g, 4.0mmol), A-7-2 (0.9g, 8.0mmol, 2.0equiv.) were added to a 50ml round-bottomed flask with tetrahydrofuran (20ml) As a solvent, sodium hydride (0.2g) was added, heated to reflux for 12 hours, cooled, filtered, and concentrated in vacuo. The final product A-7 (1.4 g, 88% yield, 99.3% purity by HPLC analysis) was obtained by column chromatography as a pale yellow solid. |