[ CAS No. 194423-15-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 194423-15-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 194423-15-9 ]

SDS Specification

Alternatived Products of [ 194423-15-9 ]

Product Details of [ 194423-15-9 ]

CAS No. :	194423-15-9	MDL No. :	MFCD02179207
Formula :	C₁₇H₁₃BrN₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HTUBKQUPEREOGA-UHFFFAOYSA-N
M.W :	369.22	Pubchem ID :	4708
Synonyms :		Chemical Name :	N-(4-((3-Bromophenyl)amino)quinazolin-6-yl)acrylamide

Calculated chemistry of [ 194423-15-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.0
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	95.43
TPSA :	66.91 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.53
Log Po/w (XLOGP3) :	3.87
Log Po/w (WLOGP) :	4.07
Log Po/w (MLOGP) :	3.05
Log Po/w (SILICOS-IT) :	3.28
Consensus Log Po/w :	3.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.75
Solubility :	0.00654 mg/ml ; 0.0000177 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.97
Solubility :	0.00394 mg/ml ; 0.0000107 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.14
Solubility :	0.0000266 mg/ml ; 0.0000000721 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.6

Safety of [ 194423-15-9 ]

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

Application In Synthesis of [ 194423-15-9 ]

* 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 [ 194423-15-9 ]

[ 194423-15-9 ] Synthesis Path-Upstream 1~8

1
[ 79-10-7 ]
[ 169205-78-1 ]
[ 194423-15-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 4.25 h;	To a solution of 6-amino-4-[(3-bromophenyl)amino]quinazoline (2.0 g, 6.35 mmol) in dry DMF (20 ML) under N2 was added acrylic acid (12.7 mmol, 0.87 mL). The resulting solution was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (7.62 mmol, 1.46 g) was added. The reaction was stirred at 0° C. for 15 minutes and then allowed to warm to room temperature and stirred for a further 2 hours, after which additional acrylic acid (0.30 mL) and EDCI.HCl (0.30 g) were added. After a further 2 hours, the reaction was complete by tlc, solvent was removed under reduced pressure, and the resulting residue diluted with saturated NaHCO3 and repeatedly extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Column chromatography on grade III alumina eluding with EtOAc/MeOH (95:5) followed by recrystallization from EtOAc/hexane gave a spongy white solid, which upon several hours under high vacuum gave N-[4-[(3-bromophenyl)amino]quinazolin-6-yl]acrylamide (1.06 g, 45percent) as a cream powder, mp 258-261° C. 1H NMR [(CD3)2SO, 200 MHz]: δ 10.51 (s, 1H, CONH), 9.93 (s, 1H, NH), 8.83 (br s, 1H, H-5), 8.59 (s, 1H, H-2), 8.18 (br s, 1H, H-2'), 7.94-7.78 (m, 3H, H-6', 8, 5'), 7.40-7.27 (m, 2H, H-7, 4'), 6.54 (dd, J =9.8 Hz, J =17.0 Hz, 1H, CH2CHCO), 6.36 (dd, J =2.1 Hz, J =16.9 Hz, 1H, CH2CHCO), 5.85 (dd, J =2.0 Hz, J =9.7 Hz, 1H, CE2CHCO). Mass spectrum (CI): 371 (95, 81BrMH+), 370 (53, 81BrM+), 369 (100, 79BrMH+), 368 (33, 79BrM+). Analysis calculated for C17H13BrN4O requires: C, 55.30; H, 3.55; N, 15.17percent. Found: C, 55.19; H, 3.34; N, 14.88percent.

Reference： [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 10, p. 1803 - 1815
[2] Patent: US6344459, 2002, B1, . Location in patent: Page column 48

2
[ 256409-20-8 ]
[ 194423-15-9 ]

Yield	Reaction Conditions	Operation in experiment
83.4%	With potassium <i>tert</i>-butylate In DMF (N,N-dimethyl-formamide) at 20℃; for 5 h;	EXAMPLE 3 4-(3-bromo phenyl amine)-6-(vinyl amide) quinazoline (II) from (7, X=O) To a solution of 4-(3-bromo phenyl amine)-6-(3-methoxy propionyl amide) quinazoline (7, X=O) (0.201 g, 0.5 mmol) in dimethyl formamide (2.5 mL), was added potassium tert-butoxide (0.178 g, 1.5 mmol). The mixture was stirred at ambient temperature for five hours, preferably overnight, until the reaction was completed (TLC/HPLC). A darkening and a small exotherm (34 °C) observed initially upon the base addition. The mixture was partition between ethyl acetate (10 mL) and aqueous sodium chloride (10 mL, 20percent). The layers were separated and the organic layer extracted to neutrality with aqueous sodium chloride (3x10 mL, 20percent), dried over anhydrous magnesium sulfate (1.5 g) for at least one hour, and the slurry filtered over a plug of silica gel (3 g). The silica gel plug was washed with a solution of ethyl acetate-10percent methanol (20 mL-2 mL), and the combined filtrates concentrated under vacuum to a yellow solid (0.200 g). Ethyl ether (5 mL) was added and the mixture stirred for one hour, filtered, and the solid washed with ethyl ether (2x0.5 mL) and dried under vacuum (60 °C) to provide the title compound as a light yellow solid, 0.154 g (83.4percent); m.p. 288-290 °C(dec.). TLC (dichloromethane-5percent methanol) showed one single spot at R_f 0.40, identical to authentic; ¹H NMR (300 MHz, DMSO-d₆) 5.85 (d, J_cis=11Hz, 1H, C=CH geminal vinyl), 6.35 (d, J_trans=15Hz, 1H, C=CH geminal vinyl), 6.54 (q, J_trans=10Hz, J_cis=7Hz, 1H, C=CH-C=O- vicinal vinyl), 7.20-8.90 (m, 8H, Ar-H), 9.94 (s, 1H, NH amide), 10.55 (s, 1H, NH amine).

Reference： [1] Patent: EP1100788, 2005, B1, . Location in patent: Page/Page column 7

3
[ 256409-24-2 ]
[ 194423-15-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 1 h;	EXAMPLE 11 4-(3-bromo phenyl amine)-6-(vinyl amide) quinazoline (II) from (12) To a solution of 4-(3-bromo phenyl amine)-6-(3-methylsulfoxido propionyl amide) quinazoline (12) (0.043g, 0.1 mmol) in DMF (2 mL), was added potassiumtert-butoxide (0.035 g, 0.3 mmol). The reaction mixture was stirred at ambient temperature for one hour, whereupon the reaction was completed (TLC/HPLC). A darkening, but no exotherm was observed initially upon the base addition. The reaction mixture was partitioned between ethyl acetate (10 mL) and aqueous sodium chloride (10 mL, 20percent). The layers were separated, the organic layer extracted to neutrality with aqueous sodium chloride (3x10 mL, 20percent), dried over anhydrous magnesium sulfate (1.5 g) for at least one hour, and filtered over a plug of silica gel (3 g). The plug was washed with a solution of ethyl acetate-10percent methanol (20 mL-2 mL). The filtrates were concentrated under vacuum to a yellow solid (0.025 g). Ethyl ether (3 mL) was added, the mixture stirred for one hour, filtered, washed with ethyl ether (3x0.5 mL) and dried it under vacuum (60 °C). The resulting light yellow solid, 0.020 g (55.0percent) was identical to the title compound (II); m.p. 288-290 °C(dec.).

Reference： [1] Patent: EP1100788, 2005, B1, . Location in patent: Page/Page column 9-10

4
[ 814-68-6 ]
[ 169205-78-1 ]
[ 194423-15-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 7, p. 3482 - 3488
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 7, p. 2892 - 2901
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2719 - 2734

5
[ 256409-22-0 ]
[ 194423-15-9 ]

Yield	Reaction Conditions	Operation in experiment
50.5%	With potassium <i>tert</i>-butylate In DMF (N,N-dimethyl-formamide) at 20℃; for 48 h;	EXAMPLE 6 4-(3-bromo phenyl amine)-6-(vinyl amide) quinazoline (II) from (7; X=S) To a solution of 4-(3-bromo phenyl amine)-6-(3-methylthio propionyl amide) quinazoline (7, X=S) (0.208g, 0.5 mmol) in dimethyl formamide (2.5 mL), was added potassium tert-butoxide (0.178 g, 1.5 mmol) and the mixture was stirred at ambient temperature. A darkening and a small exotherm (34 °C) was observed initially upon the base addition. The reaction was progressing slowly at ambient temperature and it was not completed (TLC/HPLC) after two days. The reaction mixture was partitioned between ethyl acetate (10 mL)/aqueous sodium chloride (10 mL, 20percent). The layers were separated and the organic layer was extracted to neutrality with aqueous sodium chloride (3x10 mL, 20percent). The organic layer was dried over anhydrous magnesium sulfate (1.5 g) for at least one hour and filtered over a plug of silica gel (3 g). The silica plug was washed with a solution of ethyl acetate-10percent methanol (20 mL-2 mL). The filtrate was concentrated under vacuum to a yellow solid (0.184 g) and added to ethyl ether (5 mL). The mixture was stirred for one hour, filtered; the solid was washed with ethyl ether (2x0.5 mL) and dried under vacuum (60 °C). The light yellow solid, 0.150 g (81.2percent) was a mixture of 50.5percent the title compound (II) and 38.0percent starting material (7, X=S) by HPLC. This was confirmed by TLC (dichloromethane-5percent methanol) which showed two spots in a 50/40 ratio of (1)/(11) respectively. The ¹H NMR (300 MHz, DMSO-d₆) indicated the same ratio 5/4 of the characteristic frequencies of both compounds (II) and (7) respectively.

Reference： [1] Patent: EP1100788, 2005, B1, . Location in patent: Page/Page column 8

6
[ 169205-78-1 ]
[ 194423-15-9 ]

Reference： [1] Patent: US6323209, 2001, B1,
[2] Patent: US5760041, 1998, A,
[3] Patent: US5929080, 1999, A,
[4] Patent: EP787722, 1997, A1,
[5] Patent: EP980244, 2003, B1,

7
[ 17420-30-3 ]
[ 194423-15-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2719 - 2734

8
[ 169205-77-0 ]
[ 194423-15-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2719 - 2734

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
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. 194423-15-9 ] {[proInfo.proName]}

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Product Details of [ 194423-15-9 ]

Calculated chemistry of [ 194423-15-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 194423-15-9 ]

Application In Synthesis of [ 194423-15-9 ]

[ 194423-15-9 ] Synthesis Path-Upstream 1~8

Technical Information

Related Functional Groups of [ 194423-15-9 ]

Aryls

Alkenyls

Bromides

Amides

Amines

Related Parent Nucleus of [ 194423-15-9 ]

Quinazolines

Precautionary Statements-General

Prevention

Response

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Physical hazards

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[ 194423-15-9 ]

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[ 194423-15-9 ]