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[ CAS No. 53449-14-2 ] {[proInfo.proName]}

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Chemical Structure| 53449-14-2
Chemical Structure| 53449-14-2
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Quality Control of [ 53449-14-2 ]

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Product Details of [ 53449-14-2 ]

CAS No. :53449-14-2 MDL No. :MFCD09388771
Formula : C8H4ClN3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :URDYTQYZXZKBQT-UHFFFAOYSA-N
M.W : 225.59 Pubchem ID :135687504
Synonyms :

Calculated chemistry of [ 53449-14-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.2
TPSA : 91.57 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.73
Log Po/w (XLOGP3) : 1.16
Log Po/w (WLOGP) : 1.48
Log Po/w (MLOGP) : 0.69
Log Po/w (SILICOS-IT) : 0.52
Consensus Log Po/w : 0.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.905 mg/ml ; 0.00401 mol/l
Class : Soluble
Log S (Ali) : -2.68
Solubility : 0.474 mg/ml ; 0.0021 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.13 mg/ml ; 0.000575 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 53449-14-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H320-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53449-14-2 ]

* 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.

  • Downstream synthetic route of [ 53449-14-2 ]

[ 53449-14-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 110-91-8 ]
  • [ 53449-14-2 ]
  • [ 66234-47-7 ]
  • 2
  • [ 74-89-5 ]
  • [ 53449-14-2 ]
  • [ 105664-93-5 ]
  • 3
  • [ 100-46-9 ]
  • [ 53449-14-2 ]
  • [ 53449-26-6 ]
  • 4
  • [ 53449-14-2 ]
  • [ 16292-86-7 ]
  • [ 5131-58-8 ]
  • [ 81946-23-8 ]
  • 6
  • [ 67-56-1 ]
  • [ 53449-14-2 ]
  • [ 1012057-47-4 ]
YieldReaction ConditionsOperation in experiment
77% With sodium; at 100℃; for 20h; A mixture of compound 0303 (4.0 g,18.0 mmol) and sodium (2.4 g, 45 mmol) in methanol (50 mL) was heated at 100 0C in a sealed pressure vessel for 20 hours. The solution was neutralized with acetic acid and diluted with water to give the title compound 0304 (3.0 g, 77%). 1H NMR (DMSO-J6): ￡4.10. (s, 3H), 7.40 (s, IH), <n="131"/>8.24 (s, IH), 8.50(s, IH), 12.67 (s, IH).
77% With sodium; at 100℃; for 20h; Step 22c. 7-Methoxy-6-nitroquinazolin-4(3H)-one (compound 0304); A mixture of compound 0303 (4.0 g, 18.0 mmol) and sodium (2.4 g, 45 mmol) in methanol (50 mL) was heated at 100 C. in a sealed pressure vessel for 20 hours. The solution was neutralized with acetic acid and diluted with water to give the title compound 0304 (3.0 g, 77%). 1H NMR (DMSO-d6): delta4.10 (s, 3H), 7.40 (s, 1H), 8.24 (s, 1H), 8.50 (s, 1H), 12.67 (s, 1H).
  • 7
  • [ 53449-14-2 ]
  • [ 162012-71-7 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride; In N,N-dimethyl-formamide; for 24h;Reflux; 3,4-Dihydro-6-nitro-7-chloro-4-oxoquinazoline (2 g) was placed in a 100 ml Erlenmeyer flask,After adding 40 ml of thionyl chloride and 1 drop of DMF at room temperature,Heated to reflux for 24 hours, most of the thionyl chloride was distilled off,Ice water was added, filtered and dried to give 4-chloro-6-nitro-7-chloroquinazoline (2.05 g) in 95% yield.
With trichlorophosphate; for 2h;Heating / reflux; 4.00g of the above crystalline 6-nitro-7-chloro-quinazolone was refluxed with 15 mL of phosphoryl chloride for 2h, then the reaction mixture was poured into ice water, filtered and dried to obtain the intermediate 6-nitro-4,7-dichloro- quinazoline;
With trichlorophosphate; for 2h;Heating / reflux; 4.00 g of the above crystalline 6-nitro-7-chloro-quinazolone was refluxed with 15 mL of phosphoryl chloride for 2 h, then the reaction mixture was poured into ice water, filtered and dried to obtain the intermediate 6-nitro-4,7-dichloro-quinazoline; The intermediate was dissolved into 30 mL of isopropanol, and 3.00 g of 3-chloro-4-(m-fluoro-benzyloxy)-aniline was added. The reaction mixture was reacted under reflux for 2 h and a lot of solid was deposited, which was filtered and dried under vacuum to obtain the solid product of 6-nitro-7-chloro-4-amino substituted quinazoline (3.83 g).
With phosphorus pentachloride; trichlorophosphate; In tetrachloromethane; for 2h;Reflux; 7-Chloro-6-nitro-quinazolin-4-one (1.002 g, 4.44 mmol), phosphorous oxychloride (11.5 g, 7.51 mmol) andphosphorous pentachloride (1.62 g, 7.74 mmol) were refluxed for 2 hours and the reaction mixture was concentrated invacuo to a residue which was triturated with toluene and then again with chloroform and dried in vacuo to afford crude4,7-dichloro-6-nitro-quinazoline. This was dissolved in 35 mL of isopropyl alcohol and 3-ethynylaniline (639 mg, 5.45mmol) and refluxed for 3 hours. The cooled reaction mixture was filtered to afford the title product as a solid which waswashed with 10 mL of isopropyl alcohol and dried in vacuo at 70C, 1.055 g (66%); mp 230.8-232.6C.
With triethylamine; trichlorophosphate; In acetonitrile; at 80℃; 10g of compound BB3 placed 40ml of acetonitrile, followed by adding 8.3 g of phosphorus oxychloride, 5.4 g of triethylamine, and the reaction was heated to 80 C until the reaction was complete as monitored by TLC.
With thionyl chloride; In N,N-dimethyl-formamide; for 2h;Reflux; The above-obtained 6-nitro-7-chloro-3H-quinazolin-4-one (9.0g (40.0mmol) was added to a 9011S0C12 solution and then 0.9 mL of DMF was added,Reflux stirring 2h,The solution gradually became dark yellow clear,The reaction was quenched, cooled to room temperature and excess S0C12 evaporated to give 4,7-dichloro-6-nitroquinazoline as a yellow solid. The yellow solid was crushed and added50 mL of petroleum ether. The petroleum ether was distilled off under reduced pressure and the procedure was repeated twice with petroleum ether to remove the residual S0C12 to obtain a yellow solid.The yellow solid was transferred to a three-necked flask without purification, and 3-methylaniline (4.71g, 44.0mmol), isopropanol (17101)Reflux stirring 2h, precipitation of solid, cooling to room temperature, collecting solid, washing with isopropyl alcohol, dry, yellow solid 6-nitro-7-Chloro-4- (3-methylanilino) quinazoline in a yield of 54.7%.
Examples; Example 1, synthesis of the compound: 8-allyl-4-(3-chloro-4-methoxy-benzylamino)-6-nitro-quinazolin-7-ol; 1) Synthesis of compound 5; A starting material 3 (5.7 g, 25.3 mmol) was dissolved in thionyl chloride(110.3 ml) and dimethylformamide (three drops) was added thereto at room <n="30"/>temperature. The mixture was stirred at reflux for 17 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. The solvent was removed by distillation under reduced pressure. The resulting mixture was diluted with ethyl acetate and washed with a saturated NaHCO3 solution and brine. The organic layer was dried over anhydrous sodium sulfate, distilled under reduced pressure to remove the solvents and dried under vacuum to obtain a compound. The compound and 3-chloro-4-methoxy-benzylamine (5.61 g, 27 mmol) were dissolved in isopropyl alcohol (50 ml) and triethylamine (7.56 ml, 54 mmol) was then added thereto. The resulting mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with 5% citric acid, 1 N sodium hydroxide, water and brine. The mixture was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue was eluted with dichloromethane/hexane (4 :1) to yield a compound 5 (7.8 g, 81%, 2 steps) as a yellow solid. 5 1H NMR (CD3OD, 400 MHz) delta 8.413 (s, IH), 7.907 (d, J = 2.21 Hz,IH), 7.709 (d, J = 8.92 Hz, IH), 7.637 (dd, J = 8.91, 2.28 Hz, IH), 7.408 (d,J = 2.10 Hz, IH), 7.306 (dd, J = 8.54, 2.21 Hz, IH), 7.006 (d, J = 8.44 Hz, 0IH), 4.780 (s, 2H), 3.846 (s, 3H), 3.051 (s, 3H). MS (ESI) m/z 393 (M+ + 1)

  • 8
  • [ 53449-14-2 ]
  • methyl halide [ No CAS ]
  • [ 66234-45-5 ]
YieldReaction ConditionsOperation in experiment
A portion (6 g) of the material so obtained was added portionwise to a stirred mixture of concentrated sulphuric acid (12 ml) and fuming nitric acid (12 ml) which had been cooled to 0 C. The mixture was stirred at ambient temperature for 30 minutes and then heated to 110 C. for 30 minutes. The mixture was cooled to ambient temperature and poured onto a mixture of ice and water. The precipitate was isolated, washed with water and dried. There was thus obtained 7-chloro-6-nitro-3,4-dihydroquinazolin-4-one (6.89 g).
  • 10
  • [ 53449-14-2 ]
  • butyl halide [ No CAS ]
  • [ 81946-00-1 ]
  • 11
  • [ 53449-14-2 ]
  • n-heptyl halide [ No CAS ]
  • [ 81946-01-2 ]
  • 12
  • [ 31374-18-2 ]
  • [ 53449-14-2 ]
YieldReaction ConditionsOperation in experiment
72% With sulfuric acid; nitric acid; at 0 - 90℃; for 3h; To a 100-mL flask was added concentrated sulfuric acid (10 mL),concentrated nitric acid (5 mL) and 6b (10 g, 55.4 mmol) understirring at 0 C. The mixture was heated and stirred at 90 C for 3 h.After cooling to rt, the mixture was poured onto ice-water, filtered,washed with water, dried. The crude product was recrystallizedfrom acetic acid to afford 7-chloro-6-nitroquinazolin-4(3H)-one(6c) as a light yellow solid (9 g, yield 72%). mp 315e316 C; 1H NMR(DMSO-d6, ppm): d 12.79 (b, 1H), 8.67 (s, 1H), 8.31 (s, 1H), 8.01 (s,1H).
71.2% With sulfuric acid; nitric acid; at 90℃; for 3h;Cooling with ice; 200 mL of concentrated sulfuric acid was placed in a 500 mL single-mouth round bottom flask under ice bath, and stirred.Slowly add 20 mL of concentrated nitric acid to concentrated sulfuric acid.After stirring for 30 min, it was slowly added dropwise to Intermediate 4 (50 g, 0.28 mol, 1 eq) using a constant pressure dropping funnel.The reaction solution was yellowish brown, most of the raw materials were insoluble, and the temperature was slowly raised to 90 C, and the reaction was carried out for 3 hours, and the reaction was completely confirmed by TLC. After cooling to room temperature, the reaction solution was poured into 3 L of ice water, stirred for 30 min, suction filtered, and the filter cake was washed with water.Drying, recrystallization from glacial acetic acid gave 44.5 g of a yellow solid.Yield 71.2%,
68.3% With sulfuric acid; nitric acid; at 20 - 45℃; Under ice-water bath cooling,A solution of 7-chloro-3H-quinazolin-4-one (9.00 g, 50.0 mmol)(Concentrated sulfuric acid 30mL and fuming nitric acid 30mL), plus complete, stirring at room temperature lh,Heat to 45 C and stir overnight. The reaction solution was then poured into 60 mL of ice water, filtered and the resulting solid was filtered and washed with water, recrystallized from acetic acid, dried,To give 7.78 g of 7-chloro-6-nitro-3H-quinazolin-4-one as a yellow solid in 68.3% yield.
62.7% With sulfuric acid; nitric acid; In water; at 0 - 45℃; Compound 0302 (18.0 g, 100 mmol) was added portionwise to a stirred mixture of concentrated sulfuric acid (60 mL) and fuming nitric acid (60 mL) which had been cooled to 0 0C, the mixture was stirred at ambient temperature for 1 hour and then heated to 45 0C overnight. The mixture was poured into the mixture of ice and water. The precipitate was isolated, washed with water and dried. Recrystallization from acetic acid to give the title compound 0303 (14.1 g, 62.7%). 1H NMR (DMSO-J6): delta 8.00 (s, IH), 8.27 (s, IH), 8.65 (s, IH), 12.70 (s, IH).
62.7% With sulfuric acid; nitric acid; at 0 - 45℃; Step 22b. 7-Chloro-6-nitroquinazolin-4(3H)-one (compound 0303) Compound 0302 (18.0 g, 100 mmol) was added portionwise to a stirred mixture of concentrated sulfuric acid (60 mL) and fuming nitric acid (60 mL) which had been cooled to 0 C., the mixture was stirred at ambient temperature for 1 hour and then heated to 45 C. overnight. The mixture was poured into the mixture of ice and water. The precipitate was isolated, washed with water and dried. Recrystallization from acetic acid to give the title compound 0303 (14.1 g, 62.7%). 1H NMR (DMSO-d6): delta 8.00 (s, 1H), 8.27 (s, 1H), 8.65 (s, 1H), 12.70 (s, 1H).
62.7% With sulfuric acid; nitric acid; at 0 - 45℃; Step 22b. 7-Chloro-6-nitroquinazolin-4(3H)-one (compound 0303); Compound 0302 (18.0 g, 100 mmol) was added portionwise to a stirred mixture of concentrated sulfuric acid (60 mL) and fuming nitric acid (60 mL) which had been cooled to 0 C., the mixture was stirred at ambient temperature for 1 hour and then heated to 45 C. overnight. The mixture was poured into the mixture of ice and water. The precipitate was isolated, washed with water and dried. Recrystallization from acetic acid to give the title compound 0303 (14.1 g, 62.7%). 1H NMR (DMSO-d6): delta 8.00 (s, 1H), 8.27 (s, 1H), 8.65 (s, 1H), 12.70 (s, 1H).
With sulfuric acid; nitric acid; Reference example 3: 7-chloro-6-nitro-4(3H)-quinazolone 7-Chloro-4(3H)-quinazolone (20.9 g, 0.116 mmol) obtained in Reference example 2 was dissolved in a mixed solution of concentrated sulfuric acid (45 ml) and fuming nitric acid (45 ml) and stirred at 80 C for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature and poured into ice water (900 ml). The precipitated solid was filtered off, and the filtered crude crystal was suspended in acetic acid (440 ml) and stirred at 80 C for 1 hour.
With sulfuric acid; nitric acid; at 0 - 90℃; for 3h; 10g of the above 7-chloro-quinazolone was added into a mixed acid of concentrated sulphuric acid and fuming nitric acid (40ml) slowly in an ice-bath. Then the mixture was heated to 90 and reacted at this temperature for 3h. The clear solution formed was then poured into 300mL of ice-water carefully, and yellow solid was deposited, which was filtered, washed with water and redissolved into hot acetic acid, to deposit the crystalline of 6-nitro-7-chloro-quinazolone, which was collected and 6.50g of the product was achieved.
With sulfuric acid; nitric acid; at 0 - 90℃; for 3h; 10 g of the above 7-chloro-quinazolone was added into a mixed acid of concentrated sulphuric acid and fuming nitric acid (40 ml) slowly in an ice-bath. Then the mixture was heated to 90 C. and reacted at this temperature for 3 h. The clear solution formed was then poured into 300 mL of ice-water carefully, and yellow solid was deposited, which was filtered, washed with water and redissolved into hot acetic acid, to deposit the crystalline of 6-nitro-7-chloro-quinazolone, which was collected and 6.50 g of the product was achieved.
With sulfuric acid; nitric acid; at 90℃; for 1h;Cooling with ice; The compound BB2 under 10g ice bath was slowly added concentrated sulfuric acid and fuming nitric acid (20ml: 20ml) mixed acid, the addition is complete warm to 90 C, for about 1 hour. The reaction solution was poured into 300ml of ice water, the precipitated solid was collected by filtration and the solid was the crude compound 12g BB3.

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; ;