[ CAS No. 13794-72-4 ] {[proInfo.proName]}

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2D 3D

Structure of 13794-72-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 13794-72-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13794-72-4 ]

SDS Specification

Alternatived Products of [ 13794-72-4 ]

Product Details of [ 13794-72-4 ]

CAS No. :	13794-72-4	MDL No. :	MFCD01570147
Formula :	C₁₀H₁₀N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DMSRMHGCZUXCMJ-UHFFFAOYSA-N
M.W :	206.20	Pubchem ID :	135495016
Synonyms :

Calculated chemistry of [ 13794-72-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.2
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	55.35
TPSA :	64.21 ?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) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	0.71
Log Po/w (WLOGP) :	0.94
Log Po/w (MLOGP) :	0.6
Log Po/w (SILICOS-IT) :	2.03
Consensus Log Po/w :	1.14

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.93
Solubility :	2.44 mg/ml ; 0.0118 mol/l
Class :	Very soluble
Log S (Ali) :	-1.64
Solubility :	4.76 mg/ml ; 0.0231 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.5
Solubility :	0.0657 mg/ml ; 0.000318 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 13794-72-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13794-72-4 ]

* 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 [ 13794-72-4 ]
Downstream synthetic route of [ 13794-72-4 ]

[ 13794-72-4 ] Synthesis Path-Upstream 1~1

1
[ 13794-72-4 ]
[ 1012054-59-9 ]

Reference： [1] Patent: US2009/111772, 2009, A1,

[ 13794-72-4 ] Synthesis Path-Downstream 1~4

1
[ 13794-72-4 ]
[ 16064-15-6 ]

Yield	Reaction Conditions	Operation in experiment
98.62%		(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 48% (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 (98.62% by theory) of 6,7-dihydroxy-4 (3H)-quinazolinone as off-white crystalline solid.Purity: 99.25% (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%	With hydrogen bromide; at 120℃;	6,7-dimethoxy-3H-quinazolin-4-one (25 g, 124 mmol) was stirred in HBr, 48% (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 %). 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 12h;Heating / reflux;	To 6,7-dimethoxy- 4(3H)-quinazolinone, 10 (3.0 g, 14.5 mmol) was added 48% 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, 84%).

84%		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 48% 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, 84%).
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: 80.5%.
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, cooled to -78 C under nitrogen atmosphere, and a solution of boron tribromide (10 eq) in dichloromethane (1 g) was added. /3ml). Plus,Insulation reaction for 1 h,The temperature was raised to 25 C for 4-6 h. After the reaction was completed, it was washed with 10 ml of water, dried over anhydrous sodium sulfate, and the organic layer was concentrated to dryness to yield 6.97 g of compound b, yield: 80.5%.
75%	With hydrogen bromide; acetic anhydride; at 110 - 140℃; for 31h;	10 g of the resulting product synthesized in step 1 was added in 85 ml of 40% 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 (75%). ?H NMR (400 MHz, DMSO) oe 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: CN108815167,2018,A .Location in patent: Paragraph 0063; 0065-0067
[7]Patent: US2016/175453,2016,A1 .Location in patent: Paragraph 0088; 0089
[8]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1086 - 1090

2
[ 13794-72-4 ]
[ 612501-52-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4455 - 4459

3
[ 14704-31-5 ]
[ 13794-72-4 ]
3-((biphenyl-3’-yl)methyl)-6,7-dimethoxyquinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With sodium hydride; In N,N-dimethyl-formamide; at 120℃; for 0.0833333h;Inert atmosphere; Microwave irradiation;	General procedure: A mixture of quinazolinone 19a or 19b-c (1.0 mmol) and NaH in DMF was maintained under N2 for 5 min. The appropriate haloderivative or aryloxirane was added (1.0mmol) andthe mixture was microwave irradiated at 120 C (power set point 250W; ramp time 30 sec; hold time 5 min). After cooling, the mixture was poured insat. NH4Cl solution (30 mL) and the obtained precipitate wascollected by filtration. The solid was purified by crystallization to give thetitle compounds.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 416 - 425

4
[ 13794-72-4 ]
[ 574745-97-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 147,p. 130 - 149
[2]Patent: WO2008/150118,2008,A2

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Isomers

Technical Information

? Acyl Group Substitution ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Heat of Combustion ? Hydride Reductions ? Lawesson's Reagent ? Nomenclature of Ethers ? Preparation of Amines ? Preparation of Ethers ? Reactions of Amines ? Reactions of Ethers ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes

Historical Records

Pharmaceutical Intermediates of
[ 13794-72-4 ]

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[ 179688-53-0 ]

7-Methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate

[ 621-59-0 ]

3-Hydroxy-4-Methoxybenzaldehyde

[ 788136-89-0 ]

4-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate

Related Functional Groups of
[ 13794-72-4 ]

Ethers

[ 162012-72-8 ]

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7-Methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate

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Amides

[ 162012-72-8 ]

6-Methoxy-7-hydroxyquinazolin-4-one

Similarity: 1.00

[ 179688-52-9 ]

6-Hydroxy-7-methoxyquinazolin-4(1H)-one

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7-Methoxyquinazolin-4(1H)-one

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6-(Benzyloxy)-7-methoxyquinazolin-4(1H)-one

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[ 150454-06-1 ]

4-Oxo-1,4-dihydroquinazoline-6-carboxamide

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Related Parent Nucleus of
[ 13794-72-4 ]

Quinazolines

[ 162012-72-8 ]

6-Methoxy-7-hydroxyquinazolin-4-one

Similarity: 1.00

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6-Hydroxy-7-methoxyquinazolin-4(1H)-one

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
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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

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[ CAS No. 13794-72-4 ] {[proInfo.proName]}

Quality Control of [ 13794-72-4 ]

Related Doc. of [ 13794-72-4 ]

Product Details of [ 13794-72-4 ]

Calculated chemistry of [ 13794-72-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 13794-72-4 ]

Application In Synthesis of [ 13794-72-4 ]

[ 13794-72-4 ] Synthesis Path-Upstream 1~1

[ 13794-72-4 ] Synthesis Path-Downstream 1~4

Technical Information

Pharmaceutical Intermediates of [ 13794-72-4 ]

Gefitinib Related Intermediates

Related Functional Groups of [ 13794-72-4 ]

Ethers

Amides

Related Parent Nucleus of [ 13794-72-4 ]

Quinazolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 13794-72-4 ]

Related Functional Groups of
[ 13794-72-4 ]

Related Parent Nucleus of
[ 13794-72-4 ]