[ CAS No. 125096-72-2 ]

Name: 125096-72-2|8-Bromo-4-chloroquinazoline|97%
Brand: Ambeed
SKU: A207740
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Quality Control of [ 125096-72-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 125096-72-2 ]

Product Details of [ 125096-72-2 ]

CAS No. :	125096-72-2	MDL No. :	MFCD09738589
Formula :	C₈H₄BrClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVMDCMMESVPNHN-UHFFFAOYSA-N
M.W :	243.49	Pubchem ID :	14397530
Synonyms :

Calculated chemistry of [ 125096-72-2 ]

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 :	0.0
Molar Refractivity :	52.25
TPSA :	25.78 Å²

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) :	-5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.24
Log Po/w (XLOGP3) :	3.19
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	2.58
Log Po/w (SILICOS-IT) :	3.25
Consensus Log Po/w :	2.86

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.98
Solubility :	0.0257 mg/ml ; 0.000106 mol/l
Class :	Soluble
Log S (Ali) :	-3.4
Solubility :	0.0963 mg/ml ; 0.000396 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.8
Solubility :	0.00384 mg/ml ; 0.0000158 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 125096-72-2 ]

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 [ 125096-72-2 ]

* 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.

Downstream synthetic route of [ 125096-72-2 ]

[ 125096-72-2 ] Synthesis Path-Downstream 1~48

1
[ 6318-37-2 ]
[ 125096-72-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
50%	In pyridine for 4h; Heating;

Reference： [1]Shukla; Shukla [Journal of the Indian Chemical Society, 1989, vol. 66, # 3, p. 209 - 210]

2
[ 125096-72-2 ]
[ 1784763-10-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
55%	In pyridine for 4h; Heating;

Reference： [1]Shukla; Shukla [Journal of the Indian Chemical Society, 1989, vol. 66, # 3, p. 209 - 210]

3
[ 125096-72-2 ]
[ 2360559-78-8 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
65%	In pyridine for 4h; Heating;

Reference： [1]Shukla; Shukla [Journal of the Indian Chemical Society, 1989, vol. 66, # 3, p. 209 - 210]

4
[ 125096-72-2 ]
[ 1055978-68-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
70%	In pyridine for 4h; Heating;

Reference： [1]Shukla; Shukla [Journal of the Indian Chemical Society, 1989, vol. 66, # 3, p. 209 - 210]

5
[ 98-16-8 ]
[ 125096-72-2 ]
[ 2361545-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol at 20℃;

Reference： [1]Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Kurinov, Igor; Sicheri, Frank; Zhang, Chao [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 7, p. 1074 - 1080]

6
[ 20776-51-6 ]
[ 125096-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Reflux 2: trichlorophosphate / Reflux
	Multi-step reaction with 2 steps 1: 6 h / 150 °C 2: thionyl chloride / N,N-dimethyl-formamide / 25 h / 80 °C
	Multi-step reaction with 2 steps 1: 6 h / 150 °C 2: thionyl chloride / N,N-dimethyl-formamide / 25 h / 80 °C

Reference： [1]Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Kurinov, Igor; Sicheri, Frank; Zhang, Chao [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 7, p. 1074 - 1080]
[2]Current Patent Assignee: HUAQIAO UNIVERSITY - CN112979562, 2021, A
[3]Wang, Yu; Kun Huang; Gao, Yali; Yuan, Dandan; Ling, Lin; Liu, Jieqing; Wu, Sihai; Chen, Roufen; Li, He; Xiong, Yizu; Liu, Han; Ma, Junjie [European Journal of Medicinal Chemistry, 2022, vol. 229]

7
[ 77150-35-7 ]
[ 125096-72-2 ]

Yield	Reaction Conditions	Operation in experiment
97.6%	With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 25h;	Preparation of intermediate i-2 Weigh intermediate i-1 (18 g, 0.080 mol) and place it in a 250 mL eggplant-shaped bottle, add 100 mL thionyl chloride and 1 drop of anhydrous DMF. Reflux at 80 °C for 25 h. TLC monitors the end of the reaction. After the reaction, the mixture was allowed to stand to cool to room temperature, and concentrated in vacuo to remove the solvent.Add dichloromethane to the reaction flask to the fully dissolved state, then slowly pour the product-dissolved dichloromethane solution into ice water, stir for 5 minutes, and separate the organic phase. The organic phase was washed with saturated sodium bicarbonate aqueous solution until the aqueous layer was neutral, the separated organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain 19.01 g of yellow solid, with a yield of 97.6%.
	With trichlorophosphate Reflux;

Reference： [1]Current Patent Assignee: HUAQIAO UNIVERSITY - CN112979562, 2021, A Location in patent: Paragraph 0029; 0030; 0033; 0034
[2]Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Kurinov, Igor; Sicheri, Frank; Zhang, Chao [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 7, p. 1074 - 1080]

8
[ 125096-72-2 ]
[ 2361520-26-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: isopropyl alcohol / 20 °C 2: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

Reference： [1]Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Kurinov, Igor; Sicheri, Frank; Zhang, Chao [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 7, p. 1074 - 1080]

9
[ 125096-72-2 ]
[ 57260-71-6 ]
[ 2368909-93-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine In butan-1-ol at 90℃; for 6h;	1 Step 1 A mixture of 8-bromo-4-chloroquinazoline (119) (2 g, 8 mmol), tert-butyl piperazine-1-carboxylate (1.7 g, 90 mmol) and DIPEA (2.0 g, 16 mmol) in 25 mL BuOH was heated at 90° C. for 6 hours. The solvent was removed under reduced pressure and the crude product was purified by silica gel flash chromatography, which was eluted with 0-30% EtOAc/petroleum ether and gave tert-butyl 4-(8-bromoquinazoline-4-yl)piperazine-1-carboxylate (120) as a white solid (3.0 g, 90% yield). 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.07 (d, J=7.5 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), 3.80-3.72 (m, 4H), 3.68-3.62 (m, 4H), 1.50 (s, 9H). LCMS (ESI) m/z 393, 395 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2019/233440, 2019, A1 Location in patent: Paragraph 0395; 0396

10
[ 125096-72-2 ]
[ 2368909-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 90 °C 2: potassium carbonate; palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere