[ CAS No. 31374-18-2 ] {[proInfo.proName]}

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2D 3D

Structure of 31374-18-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 31374-18-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 31374-18-2 ]

SDS Specification

Alternatived Products of [ 31374-18-2 ]

Product Details of [ 31374-18-2 ]

CAS No. :	31374-18-2	MDL No. :	MFCD00115130
Formula :	C₈H₅ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PMLONMIODRHERC-UHFFFAOYSA-N
M.W :	180.59	Pubchem ID :	135416175
Synonyms :

Calculated chemistry of [ 31374-18-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.37
TPSA :	45.75 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.19
Log Po/w (XLOGP3) :	1.4
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	1.71
Log Po/w (SILICOS-IT) :	2.72
Consensus Log Po/w :	1.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.46
Solubility :	0.629 mg/ml ; 0.00348 mol/l
Class :	Soluble
Log S (Ali) :	-1.96
Solubility :	1.96 mg/ml ; 0.0108 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.85
Solubility :	0.0255 mg/ml ; 0.000141 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 31374-18-2 ]

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

Application In Synthesis of [ 31374-18-2 ]

* 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 [ 31374-18-2 ]
Downstream synthetic route of [ 31374-18-2 ]

[ 31374-18-2 ] Synthesis Path-Upstream 1~1

1
[ 38487-86-4 ]
[ 68-12-2 ]
[ 31374-18-2 ]
[ 13165-35-0 ]

Reference： [1] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196

[ 31374-18-2 ] Synthesis Path-Downstream 1~4

1
[ 5900-59-4 ]
[ 122-51-0 ]
[ 31374-18-2 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 184

2
[ 31374-18-2 ]
[ 53449-14-2 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,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,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,p. 7988 - 7998
[13]Patent: CN103570738,2016,B .Location in patent: Paragraph 0303; 0304; 0307

3
[ 5900-59-4 ]
[ 149-73-5 ]
[ 31374-18-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 545 - 548

4
[ 123-91-1 ]
[ 5900-59-4 ]
[ 122-51-0 ]
[ 31374-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one;	EXAMPLE 2 7-Chloro-3H-quinazolin-4-one To a solution of <strong>[5900-59-4]2-amino-4-chlorobenzamide</strong> (58 g, 0.34 mol) in hot (60° C.) N-methylpyrrolidone (170 mL), triethylorthoformate (151 g, 1.02 mol, 3 equiv) and a 1,4-dioxane 5N HCl solution (ca. 15 mL) were added. The resulting solution was heated at 110° C. for 18 h. Then, the mixture was cooled to room temperature, was poured over cold water and was brought to pH 7 with saturated NaHCO3 solution. The formed precipitate was filtered, washed with water and dried to give the desired product as a slightly beige solid (58 g, 94percent). mp 253-256° C.; 1H NMR (300 MHz, MeOH-d4) delta (MeOH) 8.19 (d, J=8.6 Hz, 1H, arom), 8.10 (s, 1H, N=CH-N), 7.70 (d, J=2, 1H, arom), 7.54 (dd, J=2, J=8.6, 1H, arom). Analysis calculated for C8H5ClN2O: C 53.21; H 2.79; N 15.51. Found: C 53.46; H 2.77; N 15.48.

Reference： [1]Patent: US2003/64986,2003,A1

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

Pharmaceutical Intermediates of
[ 31374-18-2 ]

Afatinib Intermediates

[ 314771-88-5 ]

(S)-N-(3-Chloro-4-fluorophenyl)-6-nitro-7-((tetrahydrofuran-3-yl)oxy)quinazolin-4-amine

[ 314771-76-1 ]

(S)-N4-(3-Chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy)quinazoline-4,6-diamine

[ 3095-95-2 ]

2-(Diethoxyphosphoryl)acetic acid

[ 536-25-4 ]

Methyl 3-amino-4-hydroxybenzoate

[ 162012-67-1 ]

N-(3-Chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine

Related Functional Groups of
[ 31374-18-2 ]

Chlorides

[ 7142-09-8 ]

6-Chloro-2-methylquinazolin-4(3H)-one

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[ 6958-39-0 ]

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

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[ 480451-49-8 ]

6-Chloro-4-oxo-1,4-dihydroquinazoline-2-carboxylic acid

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[ 5202-85-7 ]

2-Amino-5-chlorobenzamide

Similarity: 0.72

[ 1637671-24-9 ]

6-Chloro-2-methylpyrido[3,4-d]pyrimidin-4(1H)-one

Similarity: 0.69

Amides

[ 150454-06-1 ]

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

Similarity: 0.86

[ 75844-41-6 ]

5-Methylquinazolin-4(1H)-one

Similarity: 0.82

[ 7142-09-8 ]

6-Chloro-2-methylquinazolin-4(3H)-one

Similarity: 0.80

[ 18731-19-6 ]

2,6-Dimethylquinazolin-4(1H)-one

Similarity: 0.78

[ 6958-39-0 ]

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

Similarity: 0.77

Related Parent Nucleus of
[ 31374-18-2 ]

Quinazolines

[ 150454-06-1 ]

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

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[ 75844-41-6 ]

5-Methylquinazolin-4(1H)-one

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6-Chloro-2-methylquinazolin-4(3H)-one

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[ 18731-19-6 ]

2,6-Dimethylquinazolin-4(1H)-one

Similarity: 0.78

[ 6958-39-0 ]

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

Similarity: 0.77

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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

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[ CAS No. 31374-18-2 ] {[proInfo.proName]}

Quality Control of [ 31374-18-2 ]

Related Doc. of [ 31374-18-2 ]

Product Details of [ 31374-18-2 ]

Calculated chemistry of [ 31374-18-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 31374-18-2 ]

Application In Synthesis of [ 31374-18-2 ]

[ 31374-18-2 ] Synthesis Path-Upstream 1~1

[ 31374-18-2 ] Synthesis Path-Downstream 1~4

Technical Information

Pharmaceutical Intermediates of [ 31374-18-2 ]

Afatinib Intermediates

Related Functional Groups of [ 31374-18-2 ]

Chlorides

Amides

Related Parent Nucleus of [ 31374-18-2 ]

Quinazolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 31374-18-2 ]

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[ 31374-18-2 ]

Related Parent Nucleus of
[ 31374-18-2 ]