Home Cart 0 Sign in  

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

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 53449-14-2
Chemical Structure| 53449-14-2
Structure of 53449-14-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 53449-14-2 ]

Related Doc. of [ 53449-14-2 ]

Alternatived Products of [ 53449-14-2 ]

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 ]

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 Ų

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.

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

[ 53449-14-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 31374-18-2 ]
  • [ 53449-14-2 ]
YieldReaction ConditionsOperation in experiment
72% at 0 - 90℃; for 3 h; 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 72percent). 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% at 90℃; for 3 h; 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 71.2percent,
68.3% 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 68.3percent 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, 62.7percent). 1H NMR (DMSO-J6): δ 8.00 (s, IH), 8.27 (s, IH), 8.65 (s, IH), 12.70 (s, IH).
62.7% 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, 62.7percent).
1H NMR (DMSO-d6): δ 8.00 (s, 1H), 8.27 (s, 1H), 8.65 (s, 1H), 12.70 (s, 1H).
62.7% 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, 62.7percent). 1H NMR (DMSO-d6): δ 8.00 (s, 1H), 8.27 (s, 1H), 8.65 (s, 1H), 12.70 (s, 1H).

Reference: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4096 - 4109
[2] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
[3] Patent: CN108484574, 2018, A, . Location in patent: Paragraph 0133; 0134; 0135
[4] Patent: CN103382182, 2016, B, . Location in patent: Paragraph 0272; 0273; 0276; 0277
[5] Patent: WO2008/33747, 2008, A2, . Location in patent: Page/Page column 129
[6] Patent: US2009/76022, 2009, A1, . Location in patent: Page/Page column 74
[7] Patent: US2009/111772, 2009, A1, . Location in patent: Page/Page column 73
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[9] Patent: EP1229025, 2002, A1,
[10] Patent: EP1990337, 2008, A1, . Location in patent: Page/Page column 11
[11] Patent: US2008/300248, 2008, A1, . Location in patent: Page/Page column 7
[12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7988 - 7998
[13] Patent: CN103570738, 2016, B, . Location in patent: Paragraph 0303; 0304; 0307
  • 2
  • [ 89-77-0 ]
  • [ 53449-14-2 ]
Reference: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4096 - 4109
[2] Patent: CN103570738, 2016, B,
[3] Patent: CN103382182, 2016, B,
[4] Patent: US2009/111772, 2009, A1,
[5] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
[6] Patent: CN108484574, 2018, A,
  • 3
  • [ 6280-88-2 ]
  • [ 53449-14-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 4
  • [ 74-11-3 ]
  • [ 53449-14-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 5
  • [ 5900-59-4 ]
  • [ 53449-14-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
  • 6
  • [ 53449-14-2 ]
  • [ 55496-69-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 267 - 276
[2] Patent: CN103382182, 2016, B,
[3] Patent: US2009/111772, 2009, A1,
  • 7
  • [ 367-21-5 ]
  • [ 53449-15-3 ]
  • [ 53449-14-2 ]
  • [ 179552-73-9 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: for 4 h; Heating / reflux
Stage #2: at 20℃; for 0.333333 h;
Stage #3: With triethylamine In methanol; water at 0 - 20℃; for 1 h;
1) A mixture (about 3:1, 52.0 g; described in Leonard et al., J. Org. Chem. 1975, 40, 356-363) of 7-chloro-6-nitro-3H-quinazolin-4-one and 7-chloro-8-nitro-3H-quinazolin-4-one and DMF (0.7 mL) were added to thionyl chloride (200 mL) and the mixture was heated under reflux for 4 hrs. The reaction mixture was concentrated to dryness and toluene (150 mL) was added. The mixture was concentrated further. This step was repeated twice and dichloromethane (280 mL) was added to the residue. The mixture was stirred at room temperature. To this suspension was added dropwise a solution (760 mL) of 3-chloro-4-fluoroaniline (36.9 g, 253.6 mmol) in isopropanol. Dichloromethane (300 mL) was added and the mixture was stirred, at 20° C. for 20 min. Hexane (600 mL) was added under ice-cooling, and stirring was continued at 20° C. The precipitate was collected by filtration, washed with hexane (200 mL.x.2) and dried under reduced pressure. The obtained solid was added to methanol (1 L)-water (120 mL), and triethylamine (30 mL) was added with stirring under ice-cooling. After stirring at room temperature for 1 hr, the precipitate was collected by filtration and washed with water (700 mL.x.2). The crudely purified substance (65 g) was suspension-washed with acetonitrile (1.2 L) with heating, and collected by filtration to give the objective (7-chloro-6-nitro-4-quinazolinyl)-(3-chloro-4-fluorophenyl)amine (54.6 g, 67percent).
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 30
  • 8
  • [ 367-21-5 ]
  • [ 53449-14-2 ]
  • [ 179552-73-9 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With thionyl chloride In N,N-dimethyl-formamide for 3 h; Reflux
Stage #2: at 90℃; for 1 h;
To a 250 mL four-necked flask was added 2.3 g (10.2 mmol)7-chloro-6-nitroquinazolin-4-one (7), 3 to 4 drops of DMF and 10 mL of thionyl chloride,Stirring to reflux, 30min after the solid completely dissolved, reflux reaction 2.5h,Sulfur disulfide was evaporated to give a pale yellow solid.To the reaction flask was added 1.8 g (12.2 mmol)3-chloro-4-fluoroaniline and 1,4-dioxane solution 25mL,Added, the reaction was yellow turbid liquid, slowly warming to 90 ,And reacted at that temperature for 1 h. After cooling to room temperature, pour into the water,Precipitation of light orange solid, with saturated aqueous sodium bicarbonate solution to neutral,Filtered, washed with water and dried to give 3.5 g of an orange solid, 98percent yield,Purity 96percent.
70%
Stage #1: With trichlorophosphate In acetonitrile at 80℃; for 5 h;
Stage #2: for 1 h;
The phosphorus oxychloride (phosphorous oxy chloride) 10 ml melting was dissolved in 7- chloro- 6- nitro quinazoline - 4 (3H) -one 11 (5 g, 22.16 mmol) which were the starting material in the CH CN of 30 ml was added and the mixture was stirred at 80 for 5 hours. After 5 hours, 3-chloro-4-fluoroaniline (3.871 g, 26.59 mmol) dissolved in 10 ml of dioxane was added dropwise thereto, followed by stirring for 1 hour. After the completion of the reaction was confirmed by TLC, the pH of the solution was adjusted to between 8 and 10 with 2N KOH solution, and the resulting solid was filtered. The solid compound was washed with water and ethanol, and then Compound 12 (6.574 g, 18.61 mmol , 70percent) was obtained
Reference: [1] Patent: CN106565692, 2017, A, . Location in patent: Paragraph 0040; 0041
[2] Patent: KR2017/15848, 2017, A, . Location in patent: Paragraph 0129-0131
  • 9
  • [ 53449-14-2 ]
  • [ 179552-73-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7988 - 7998
[2] Patent: CN103570738, 2016, B,
[3] Patent: CN107674059, 2018, A,
  • 10
  • [ 53449-14-2 ]
  • [ 179552-75-1 ]
Reference: [1] Patent: US2009/111772, 2009, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 53449-14-2 ]

Chlorides

Chemical Structure| 6958-39-0

[ 6958-39-0 ]

6,7-Dichloroquinazolin-4(3H)-one

Similarity: 0.78

Chemical Structure| 17518-98-8

[ 17518-98-8 ]

7-Bromo-6-chloroquinazolin-4(3H)-one

Similarity: 0.69

Chemical Structure| 16588-34-4

[ 16588-34-4 ]

4-Chloro-3-nitrobenzaldehyde

Similarity: 0.69

Chemical Structure| 858238-17-2

[ 858238-17-2 ]

7-Chloro-6-methoxyquinazolin-4(3H)-one

Similarity: 0.67

Chemical Structure| 35982-55-9

[ 35982-55-9 ]

6-Chloro-2-(trifluoromethyl)quinazolin-4(3H)-one

Similarity: 0.67

Amides

Chemical Structure| 6943-17-5

[ 6943-17-5 ]

6-Nitroquinazolin-4(3H)-one

Similarity: 0.84

Chemical Structure| 20872-93-9

[ 20872-93-9 ]

7-Nitroquinazolin-4(3H)-one

Similarity: 0.83

Chemical Structure| 6958-39-0

[ 6958-39-0 ]

6,7-Dichloroquinazolin-4(3H)-one

Similarity: 0.78

Chemical Structure| 17329-31-6

[ 17329-31-6 ]

6-Aminoquinazolin-4(3H)-one

Similarity: 0.70

Chemical Structure| 17518-98-8

[ 17518-98-8 ]

7-Bromo-6-chloroquinazolin-4(3H)-one

Similarity: 0.69

Nitroes

Chemical Structure| 6943-17-5

[ 6943-17-5 ]

6-Nitroquinazolin-4(3H)-one

Similarity: 0.84

Chemical Structure| 20872-93-9

[ 20872-93-9 ]

7-Nitroquinazolin-4(3H)-one

Similarity: 0.83

Chemical Structure| 162012-69-3

[ 162012-69-3 ]

7-Fluoro-6-nitroquinazolin-4(3H)-one

Similarity: 0.73

Chemical Structure| 16588-34-4

[ 16588-34-4 ]

4-Chloro-3-nitrobenzaldehyde

Similarity: 0.69

Chemical Structure| 1027929-81-2

[ 1027929-81-2 ]

7-Fluoro-8-nitroquinazolin-4(3H)-one

Similarity: 0.69

Related Parent Nucleus of
[ 53449-14-2 ]

Quinazolines

Chemical Structure| 6943-17-5

[ 6943-17-5 ]

6-Nitroquinazolin-4(3H)-one

Similarity: 0.84

Chemical Structure| 20872-93-9

[ 20872-93-9 ]

7-Nitroquinazolin-4(3H)-one

Similarity: 0.83

Chemical Structure| 6958-39-0

[ 6958-39-0 ]

6,7-Dichloroquinazolin-4(3H)-one

Similarity: 0.78

Chemical Structure| 162012-69-3

[ 162012-69-3 ]

7-Fluoro-6-nitroquinazolin-4(3H)-one

Similarity: 0.73

Chemical Structure| 17329-31-6

[ 17329-31-6 ]

6-Aminoquinazolin-4(3H)-one

Similarity: 0.70