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[ CAS No. 16064-15-6 ] {[proInfo.proName]}

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Chemical Structure| 16064-15-6
Chemical Structure| 16064-15-6
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Product Details of [ 16064-15-6 ]

CAS No. :16064-15-6 MDL No. :MFCD14583012
Formula : C8H6N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :NDHAHRQOSZIMIN-UHFFFAOYSA-N
M.W : 178.14 Pubchem ID :135742258
Synonyms :

Calculated chemistry of [ 16064-15-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 46.41
TPSA : 86.21 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.6
Log Po/w (XLOGP3) : 0.06
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : -0.02
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 0.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.55
Solubility : 5.0 mg/ml ; 0.0281 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 6.71 mg/ml ; 0.0377 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.08
Solubility : 1.47 mg/ml ; 0.00826 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 16064-15-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16064-15-6 ]

* 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.

  • Upstream synthesis route of [ 16064-15-6 ]
  • Downstream synthetic route of [ 16064-15-6 ]

[ 16064-15-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 13794-72-4 ]
  • [ 16064-15-6 ]
YieldReaction ConditionsOperation in experiment
98.62%
Stage #1: With hydrogen bromide In water at 110℃; Reflux
Stage #2: With ammonia In water
(i) Preparation of 6,7-dihydroxy-4 (3H)-quinazolinone of formula (9)Into a 2.0 Lt four necked round bottomed flask equipped with a mechanical stirrer, reflux condenser and thermometer socket are charged 48percent (w/w) hydrobromic acid (1000 g) and 6,7-dimethoxy-4 (3H)-quinazolinone (100 g). Slowly heated the reaction mass to reach 110° C. and maintained for 1 hour at the same temperature. Then raised mass temperature to reach reflux condition and refluxed for 12 hours. Monitored the completion of the reaction by TLC. Then cooled the reaction mass to 25-35° C. and filtered the mass. Transferred the wet cake into another 2.0 Lt round bottomed flask containing 1000 ml of DM water. Stirred for 10-15 minutes and adjusted the pH to 7.0-7.5, by adding aqueous ammonia solution. Filtered the resulting product and washed the cake with DM water and dried to get 85.2 g (98.62percent by theory) of 6,7-dihydroxy-4 (3H)-quinazolinone as off-white crystalline solid.Purity: 99.25percent (by HPLC)Melting point: >250° C.IR (KBr): 3208.7, 1679.0, 1614.5, 1514.7, 1427.7, 1374.3, 1316.2, 1293.9, 1261.0, 1214.5, 1195.5, 866.0, 845.3, 780.7, 523.8, and 449.2 cm-1.1H NMR (300 MHz, DMSO-D6): 6.93 (s, 1H); 7.35 (s, 1H); 7.84 (s, 1H); 9.75 (s, 1H); 10.13 (s, 1H); 11.2-12.4 (s, 1H).Mass: 179 (M+1), 177 (M-1).
97% at 120℃; 6,7-dimethoxy-3H-quinazolin-4-one (25 g, 124 mmol) was stirred in HBr, 48percent (150 mL) at 120 °O overnight. The mixture was cooled to room temperature and filtered. The filter cake was stirred in water and treated with ammonium hydroxide to pH = 8 and the mixture was filtered. The filter cake was stirred in acetone and the resulting mixture was filtered. The filter cake was washed with diethyl ether and dried giving the desired product as a fine, pale powder (21 g, 97 percent). 1H NMR (d6-DMSO) O 11.82 (brs, 1H), 10.13 (5, 1 H), 9.75 (5, 1 H), 7.84 (5, 1 H), 7.34 (5, 1 H), 6.92 (5, 1 H).
84% With hydrogen bromide In water at 120℃; for 12 h; Heating / reflux To 6,7-dimethoxy- 4(3H)-quinazolinone, 10 (3.0 g, 14.5 mmol) was added 48percent HBr (36 mL) and the solution was heated to reflux at 100 0C for 12 h. The reaction mixture was cooled to room temperature and the solids were filtered. The solid obtained was neutralized with aq. NH3 (pH = 8) and the solution was filtered and washed with water and dried to give 6,7-dihydroxy-4(3H)-quinazolinone, 11 as a off-white crystalline solid (2.20 g, 84percent).
84%
Stage #1: at 100℃; for 12 h;
Stage #2: With ammonia In water
Step 1. 6,7-Dihvdroxy-4(3H)-quinazorinone (11). A solution of 6,7- dimethoxy-4(3H)-quinazolinone 10 (3.0 g, 14.5 mmol) and 48percent HBr (36 mL) was heated to reflux at 100 0C for 12 hours. The reaction mixture was cooled to room temperature and the solids were removed by filtration then neutralized with aqueous NH3 (pH = 8). The resulting solution was filtered and the solids were washed with water and dried to give 6,7-dihydroxy-4(3H)-quinazolinone 11 as an off-white crystalline solid (2.20 g, 84percent).
80.5% With boron tribromide In dichloromethane at -78 - 25℃; Inert atmosphere (1)Compound a (10 g, 1.0 eq) and dichloromethane (100 ml) were added to a three-necked flask under nitrogen.The temperature was lowered to -78 ° C, and a solution of boron tribromide (10 eq) in dichloromethane (1 g / 3 ml) was added.After the addition, the reaction was kept for 1 h, and the temperature was raised to 25 ° C for 4-6 h.After the reaction is over,Wash with 10 ml of water and dry over anhydrous sodium sulfate.Concentrate the organic phase to dryness,Over the fast column,Yielding 6.97 g of compound b,Yield: 80.5percent.
75% at 110 - 140℃; for 31 h; 10 g of the resulting product synthesized in step 1 was added in 85 ml of 40percent H13r solution, and then the mixture was slowly added with 30 ml of acetic anhydride in a water bath. The water bath is removed, and the system was heated to 110° C. in an oil bath, reacted for 1 hr, then heated to 140° C. and reacted for 30 hrs. A large amount of white solids was precipitated in the flask. The reaction solution was filtered after cooled. The filter cake was dissolved in 75 ml of water, and the mixture was added with aqua ammonia until the pH value was adjusted to 9 and then filtered. The filter cake was washed with 75 ml of 1M NaHCO3 solution and dried to obtain 6.5 g of the resulting product (75percent). ‘H NMR (400 MHz, DMSO) ö 7.78 (s, 1H), 7.29 (s, 1H), 6.84 (s, 1H)

Reference: [1] Patent: US2009/306377, 2009, A1, . Location in patent: Page/Page column 5-6
[2] Patent: WO2016/123706, 2016, A1, . Location in patent: Paragraph 00170
[3] Patent: WO2008/76949, 2008, A2, . Location in patent: Page/Page column 11; 29
[4] Patent: WO2009/121042, 2009, A1, . Location in patent: Page/Page column 39
[5] Patent: CN108727400, 2018, A, . Location in patent: Paragraph 0055; 0057; 0059
[6] Patent: US2016/175453, 2016, A1, . Location in patent: Paragraph 0088; 0089
[7] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 10, p. 1086 - 1090
  • 2
  • [ 4101-33-1 ]
  • [ 16064-15-6 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen bromide In water at 110 - 140℃; for 16 h; In a 250 ml_ flask, a mixture of 6,7-dimethoxy-4-(3H)-quinazoline (20.00 g, 97.0 mmol) and 48percent HBr (200 g, 133 ml_) was heated at 1 10 °C and was stirred for 1 h. The mixture was heated to 140 °C and was stirred for 15 h. The resulting suspension was cooled to 20 °C and was filtered. The collected solid was suspended in H2O (150 ml_) and NH4OH was added to pH 9. The suspension was filtered and the resulting solid was suspended in 1 MNaHCO3 (150 ml_). The solid was filtered, was washed with H2O (50 ml_) and was dried to give the title compound as a white solid (16.82 g, 97percent yield). 1H NMR (d6-DMSO, ppm): δ 7.79 (s, 1 H), 7.32 (s, 1 H), 6.88 (s, 1 H).
97%
Stage #1: at 110 - 140℃; for 16 h;
Stage #2: With ammonium hydroxide In water
Example 1: Preparation of 6,7-dihydroxyauinazolinone In a 250 mL flask, a mixture of 6,7-dimethoxy-4-(3H)-quinazoline (20.00 g, 97.0 mmol) and 48percent HBr (200 g, 133 mL) was heated at 110 °C and was stirred for 1 h. The mixture was heated to 140 °C and was stirred for 15 h. The resulting suspension was cooled to 20 °C and was filtered. The collected solid was suspended in H2O (150 mL) and NH4OH was added to pH 9. The suspension was filtered and the resulting solid was suspended in 1 M NaHCO3 (150 mL). The solid was filtered, was washed with H2O (5 mL) and was dried to give the title compound as a white solid (16.82 g, 97percent yield). 1H NMR (d6-DMSO, ppm): δ 7.79 (s, 1 H), 7.32 (s, 1 H), 6.88 (s, 1 H).
Reference: [1] Patent: WO2011/76813, 2011, A1, . Location in patent: Page/Page column 12-13
[2] Patent: EP2348020, 2011, A1, . Location in patent: Page/Page column 8
  • 3
  • [ 179688-53-0 ]
  • [ 16064-15-6 ]
YieldReaction ConditionsOperation in experiment
100% at 180℃; for 4 h; 6,7-Dihydroxyquinazolinone (2) To an excess of stirred molten pyridinium hydrochloride at 180 °C was added portionwise 6-acetoxy-7-methoxy-quinazolone (1) (49.5 g, 211.35 mmol) and the resulting solution was stirred at 180 °C for 4 hours. After cooling to room temperature, water (500 ml) was added and the pH adjusted to 7 with aqueous ammonia. The resulting precipitate was collected by filtration, washed with water (5 x 20 ml), ether (5 x 20 ml) and dried to a constant weight in a vacuum oven at 40 °C to afford 6,7-dihydroxyquinazolinone (2) (38 g, 100percent) as a beige solid: LCMS (retention time = 0.97 min., purity = 98percent), ESI+ m/z 179.18 (M+H)+; 'H- NMR (DMSO-d6) δ (ppm) 6.95 (s, 1H), 7.41 (s, 1H), 7.91 (s, 1H), 9.78 (s, 1H), 10.23 (s, 1H), 11.7 (br s, 1H).
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 14, p. 1600 - 1602
[2] Patent: WO2014/200872, 2014, A1, . Location in patent: Page/Page column 83; 84
  • 4
  • [ 26759-46-6 ]
  • [ 16064-15-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 10, p. 1086 - 1090
[2] Patent: US2016/175453, 2016, A1,
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