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CAS No. : | 60547-97-9 | MDL No. : | MFCD00563872 |
Formula : | C14H19N5O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 289.33 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | 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 |
---|---|---|
With dmap; dicyclohexyl-carbodiimide In 1,4-dioxane at 22 - 25℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In water at 100℃; for 6h; | |
80.8% | In water at 100℃; for 6h; | |
78% | In i-Amyl alcohol for 30h; Reflux; |
68% | With palladium diacetate; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 20℃; for 12h; | |
68% | With sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; | |
In butan-1-ol at 100℃; for 24h; | Compounds 1-24, 27 and 28 were prepared as the following procedure The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100°C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different substituted acetyl chloride and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(naphthalen-2-yl)methanone(1) White solid, melting point 2226-229°C, 72% yield for the last step; 1H-NMR (400MHz, DMSO-d6) δ 8.016 (4H, m), 7.580 (3H, m), 7.440 (1H, s), 7.167 (2H, br), 6.745 (1H, s), 3.795 (12H, m), 3.490 (2H, br). 13C-NMR (100MHz, DMSO-d6) δ 169.642, 161.632, 158.757, 154.699, 149.117, 145.535, 133.709, 132.754, 130.970, 129.745, 128.525, 127.826, 125.353, 105.645, 104.111, 103.460, 67.487, 56.294, 66.889, 25.592. DUIS-MS calculated for C25H25N5O4 [M+H]+: 444.1, found: 443.5. | |
In butan-1-ol at 100℃; for 24h; | 2 Compounds 1-24, 27 and 28 were prepared as the following procedure The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1 to 5 mole ratio, and the mixture was heated to 100°C for 24 hours, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different substituted acetyl chloride and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CC>3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the (0403) corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In methanol at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In methanol; dichloromethane; butan-1-ol; | A solution of 4-amino-6,7-dimethoxy-2-piperazinyl-quinazoline (12.05 g), <strong>[3705-87-1]2-chloro-1-(1-methylethyl)benzimidazole</strong> (6.55 g), triethylamine (21.5 ml) in butanol (600 ml) was refluxed for 72 hr and evaporated. The residue was chromatographed through silica gel using 10% methanol in dichloromethane and the appropriate fractions were evaporated to give a residue (5.37 g) of the title compound. The residue was crystallized from methanoldichloromethane: mp>250 C.; ir (CHCl3) 3520, 3410 and 1240 cm-1; uv max (MeOH) 250 (epsilon=67,500), 278 (epsilon=26,300), 282 (epsilon=26,000) and 342 (epsilon=6,750); nmr (CDCl3) delta 1.6 (d, 6H), 3.3 (s, 4H), 3.85 (s, 3H), 3.95 (s, 3H), 4.0 (m, 4H), 4.7 (m, 1H), 5.2 (s, 2H) and 7.2 (m, 6H); and Anal. Calcd. for C24 H29 N7 O2: C, 64.41% H, 6.53% N, 21.91% and Found: C, 64.04% H, 6.59% N, 21.86%. In the same manner, but replacing <strong>[3705-87-1]2-chloro-1-(1-methylethyl)benzimidazole</strong> with an equivalent amount of 2-chloro-1-propylbenzimidazole, the following compound of formula Ia was obtained; 6,7-dimethoxy-2-[4-(1-propyl-1H-benzimidazol-2-yl)-1-piperazinyl]-4-quinazolinamine: mp 250 C. (crystallized from dichloromethane-methanol); ir (nujol) 3440, 3320, 3210, 1645, 1245 and 1105 cm-1; uv max (MeOH) 341 (epsilon=6,650), 288 (epsilon=26,100), 278 (epsilon=26,100) and 250 nm (epsilon=66,700); and Anal. Calcd. for C24 H29 N7 O2: C, 64.41% H, 6.53% N, 21.91% and Found: C, 64.00% H, 6.53% N, 21.89%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; | Example 97 4-Amino-6,7-dimethoxy-2-[4-(5-methylisoxazole-3-carbonyl)-piperazin-1-yl]quinazoline Hydrochloride A solution of <strong>[39499-34-8]5-methylisoxazole-3-carbonyl chloride</strong> (0.41 g., 2.83 mmole) in dioxane was added to a solution of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline (0.82 g., 2.83 mmole) in dioxane. The mixture was treated as described in the previous example to give the title compound having a m.p. of 271-273 C. with decomposition. Anal. Calcd. for C19H22N6O4HCl H2O: C, 50.38; H, 5.56; N, 18.56; H2O, 3.92. Found: C, 50.58; H, 5.40; N, 18.86; H2O, 3.72. | |
In 1,4-dioxane; | EXAMPLE 4 4-Amino-6,7-dimethoxy-2-[4-(5-methylisoxazole-3-carbonyl)piperazin-1-yl]quinazoline Hydrochloride A solution of <strong>[39499-34-8]5-methylisoxazole-3-carbonyl chloride</strong> (0.41 g., 2.83 mmole) in dioxane was added to a solution of 4-amino-6,7-dimethoxy-2-(1-piperazinyl) quinazoline (0.82 g., 2.83 mmole) in dioxane. The mixture was treated as described in the previous example to give the title compound having a m.p. of 271-273 C. with decomposition. Anal. Calcd. for C19 H22 N6 O4. HCl H2 O: C, 50.38; H, 5.56; N, 18.56; H2 O, 3.92. Found: C, 50.58; H, 5.40; N, 18.86; H2 O, 3.72. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; water; | EXAMPLE 3 Prazosin Hydrochloride, gamma-Form 2-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline (57.8 g., 0.20 mole) was dissolved in 1000 ml. of chloroform and 30.2 g. (0.20 mole) of 2-furoyl chloride was added slowly at ambient temperature. When the addition was completed the resulting slurry was stirred for 15 minutes after which 1000 ml. of isoamyl alcohol was added. To the resulting mixture was then added sufficient 10% (w/w) aqueous sodium hyroxide solution to effect the solution of the solid material, about 200 ml. was ordinarily required, while maintaining the mixture at room temperature. The aqueous layer was separated and the organic phase was washed with 250 ml. of water. The organic layer was dried over anhydrous MgSO4, filtered and the filtrate cooled to 0 C. Anhydrous hydrogen chloride was passed through the solution at 0-5 C. until the solution was acidic to moistened test paper (pH about 2-2.5), about 45 minutes was required for the addition. The chloroform was then evaporated at reduced pressure while warming gently to about 45 at 20-30 mm Hg. The vacuum was then released and the solution heated to about 100 C. to remove the last traces of chloroform. The mixture was then allowed to cool to room temperature. The product was recovered by filtration, washed with chloroform and dried in the vacuum oven at 50-60 C. to afford 73.9 g. of needle-like crystals, M.P. 277-279 C. (dec.) of the title polymorph. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; | Example 94 4-Amino-6,7-dimethoxy-2-[4-(isoxazole-5-carbonyl)-piperazine-1-yl]quinazoline Hydrochloride A solution of <strong>[62348-13-4]isoxazole-5-carbonyl chloride</strong> (1.33 g., 0.01 mole) in dioxane was added to a solution at 30 C. of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline (2.94 g., 0.01 mole) in dioxane. The mixture was stirred at reflux for three minutes, then at room temperature for 16 hours. Filtration gave the title compound (4.02 g., 94% yield). Recrystallization from aqueous methanol gave a product having a m.p. of 270 C. with decomposition. Anal. Calcd. for C18H20N6O4S.HCl: C, 51.37; H, 5.03; Cl, 8.42; N, 19.97. Found: C, 50.86; H, 4.65; Cl, 8.52; N, 19.81 (corrected for 4.30% H2O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 25 - 28℃; | 1 Example 1 2,3-dihydro-1,4-benzodioxine-2-carboxylic acid (0.38 mol; 68.51 g) and tetrahydrofuran (500 ml) were charged and contents were stirred at 20-25° C. for 5-10 min to get a clear solution. N,N-carbonyl diimidazole (0.407 mol; 66.28 g) along with tetrahydrofuran (500 ml) was added to the solution and stirring continued at 20-25° C. for 2 hr to obtain solution A. In another round bottom flask, 6,7-dimethoxy-2-(piperazin-1-yl)quinazolin-4-amine (0.346 mol; 100 g) and tetrahydrofuran (1000 ml) were charged and stirred at 26-28° C. for 5-10 min to obtain a slurry. Solution A was added dropwise within 2-2.5 hr at 25-28° C. to the slurry. The reaction was monitored by HPLC. To the resulting clear reaction mass charcoal was added and contents were stirred at 26-28° C. for 45 min. The contents were filtered through celite and washed with tetrahydrofuran. The solvent was distilled out at 35° C. under reduced pressure to obtain solid residue. Acetone (1000 ml) was added to the solid and contents were refluxed for 2 hr. On cooling to 25-28° C., the slurry was filtered, washed with acetone and dried at 60° C. under reduced pressure to obtain 110 g of doxazosin base (HPLC purity -99.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 - 20℃; for 5.16667h; | 2-iodophenol as raw materials, synthesis of racemic doxazosin, the reaction line as follows:1. Synthesis of Compound c: The same procedure as in Example 1, c.2. Synthesis of compound f (i.e., doxazosin racemate)Compounds c were weighed into eggplant flasks,Plus tetrahydrofuran dissolved,The mixture was stirred for 5-10 minutes at room temperature until compound c was completely dissolved.N, N'-carbonyldiimidazole (1.1 equiv) was weighed and dissolved in tetrahydrofuran,Was slowly added dropwise to the above solution,The mixture was stirred at room temperature for 1 hour,The solution A was obtained.Another take a pickle-shaped bottle,The compound g (2-piperazinyl-4-amino-6,7-dimethoxyquinazoline) (1.0 equiv)Followed by stirring for 10 minutes with tetrahydrofuran. Solution A was slowly added dropwise to solution B at 0 ° C, and the reaction was allowed to proceed to room temperature for 4 hours after completion of dropwise addition. The solid was filtered off. The solid was dissolved in acetone and refluxed for 6 hours. Upon cooling to room temperature, the solid was filtered off and washed with acetone and dried to give a white solid as Compound f (doxazosin racemate). Yield 80percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide | Compounds 1-24, 27 and 28 were prepared as the following procedure General procedure: The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100°C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different substituted acetyl chloride and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide | Compounds 1-24, 27 and 28 were prepared as the following procedure General procedure: The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100°C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different substituted acetyl chloride and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide | Compounds 1-24, 27 and 28 were prepared as the following procedure General procedure: The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100°C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different substituted acetyl chloride and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; | General procedure: The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different substituted acetyl chloride and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In acetonitrile; at 80℃; for 5h;Inert atmosphere; | General procedure: The 1-(2-methoxyphenyl)piperazine (0.83 g, 4.3 mmol), the 1 (1.43 g, 5.3 mmol) (1.2 equiv) and K2CO3 (1.25 g, 9 mmol) (2.1 equiv) were heated to reflux in 25 mL CH3CN solvent for 5 h under nitrogen atmosphere. Then the mixtures cooled down to room temperature. Then evaporated the solvent in vacuo and the residue dissolved in H2O and extracted with ethyl acetate. The organic layer was washed by brine and dried by MgSO4. Filtered and the solvent evaporated in vacuo, separated by column chromatography (50 % petroleum ether and 50 % ethyl acetate) to give the product as a yellow oil (1.52 g, 92 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide | 4.1.1 Compounds 3a-3f were prepared as the following procedure General procedure: The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100°C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different linkers and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide | 4.1.1 Compounds 3a-3f were prepared as the following procedure General procedure: The dimethoxyquinazolin and piperazine were dissolved in n-BuOH with 1-5mol ratio, and the mixture was heated to 100°C for 24h, then it was cooled down to room temperature. The precipitated while solid was collected via filtration and washed with n-BuOH. After it was dried, the solid was mixed with various different linkers and K2CO3 in DMF. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate | 4.1.8 Compounds 5a-5f were prepared as the following procedure General procedure: The dimethoxyquinazolin and piperazine product was mixed with various different substituted acetyl chloride and K2CO3 in THF/H2O one to one mixture. It was stirred until the reaction was completed. The reaction was quenched with Na2CO3 aqueous solution and stirred overnight, and the precipitated product was collected via filtration and washed with water and dried to give the corresponding compounds. |
Tags: 60547-97-9 synthesis path| 60547-97-9 SDS| 60547-97-9 COA| 60547-97-9 purity| 60547-97-9 application| 60547-97-9 NMR| 60547-97-9 COA| 60547-97-9 structure
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H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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