[ CAS No. 848369-52-8 ]

Name: 848369-52-8|2-(Chloromethyl)-8-methylquinazolin-4(3H)-one|95%
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Quality Control of [ 848369-52-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 848369-52-8 ]

CAS No. :	848369-52-8	MDL No. :	MFCD07324008
Formula :	C₁₀H₉ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LTOSAQRHTJQRRM-UHFFFAOYSA-N
M.W :	208.64	Pubchem ID :	135530878
Synonyms :

Calculated chemistry of [ 848369-52-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.09
TPSA :	45.75 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) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	1.68
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	2.04
Log Po/w (SILICOS-IT) :	3.47
Consensus Log Po/w :	2.14

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.65
Solubility :	0.462 mg/ml ; 0.00222 mol/l
Class :	Soluble
Log S (Ali) :	-2.26
Solubility :	1.16 mg/ml ; 0.00556 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.65
Solubility :	0.00467 mg/ml ; 0.0000224 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 848369-52-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 848369-52-8 ]

* 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 [ 848369-52-8 ]

[ 848369-52-8 ] Synthesis Path-Downstream 1~41

1
[ 848369-52-8 ]
[ 17422-74-1 ]
[ 941028-33-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With chloro-trimethyl-silane In N,N-dimethyl-formamide for 18h; Heating;

Reference： [1]Plaskon, Andrey S.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A. [Synthesis, 2008, # 7, p. 1069 - 1077]

2
[ 4389-45-1 ]
[ 107-14-2 ]
[ 848369-52-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: chloroacetonitrile With sodium In methanol at 20℃; for 1.16667h; Inert atmosphere; Stage #2: 3-methylantranilic acid In methanol at 20℃; for 2h;	Int-A1: 2-(Chloromethyl)-8-methylquinazolin-4(3H)-one Chloroacetonitrile (75 g, 0.99 mol, 3 eq) was added dropwise to a pre-prepared solution of sodium (1.52 g, 6.6 mmol, 0.2 eq) in methanol (200 mL) over 10 mins at RT under a nitrogen atmosphere. After stirring for 1 h, a solution of 2-amino-3-methylbenzoic acid (50 g, 0.33 mmol, 1.0 eq) in methanol (700 mL) was added and the mixture was stirred at RT for another 2 h. The resulting precipitate was collected by filtration and washed with water then MeOH and dried under vacuum to give the title compound (46.9 g, 68%) as a white solid. LCMS: [M+H]+ 209.0. The following intermediates in Table 1 were similarly prepared from the appropriate amino acid starting material according to the method described for Int-A1.
58%	Stage #1: chloroacetonitrile With sodium In methanol at 25℃; for 0.666667h; Inert atmosphere; Stage #2: 3-methylantranilic acid In methanol at 25℃; for 2h; Inert atmosphere;

Reference： [1]Current Patent Assignee: RIBON THERAPEUTICS INC - US2019/194174, 2019, A1 Location in patent: Paragraph 0225; 0226
[2]Location in patent: experimental part Li, Hong-Ze; He, Hai-Yun; Han, Yuan-Yuan; Gu, Xin; He, Lin; Qi, Qing-Rong; Zhao, Ying-Lan; Yang, Li [Molecules, 2010, vol. 15, # 12, p. 9473 - 9485]

4
[ 848369-52-8 ]
[ 131242-36-9 ]
8-methyl-2-((pyrimidin-2-ylthio)methyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	Stage #1: 2-sulfanylpyrimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-(chloromethyl)-8-methylquinazolin-4(3H)-one In N,N-dimethyl-formamide at 20℃; for 0.333333h;
36%	Stage #1: 2-sulfanylpyrimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-(chloromethyl)-8-methylquinazolin-4(3H)-one In N,N-dimethyl-formamide at 20℃; for 0.333333h;	1 General procedure for synthesis of ((pyrimidin-2-ylthio)methyl)quinazolin-4(3H)-ones: General procedure: The appropriate thiol (2 eqv.) and sodium hydride (2 eqv.) were dissolved in anhydrous DMF and stirred at RT for 20 min. The appropriate quinazolin-4(3H)-one was added as a solid and the reaction mixture stirred at RT for 20 min. Once complete by TLC analysis (100% EtOAc) the reaction was poured over water, isolated, and purified as indicated.Example 1. 8-methyl-2-((pyrimidin-2-ylthio)methyl)quinazolin-4(3H)-one, QDR2: From 2-(chloromethyl)-8- methylquinazolin-4(3H)-one(112 mg, 0.54 mmol); reaction was concentrated in vacuo and product recovered as a white solid; yield 55.3 mg (36%); 1 H NMR (400 MHz, DMSO-c/6) d 12.46 (s, 1 H), 8.70 (d, J = 4.9 Hz, 2H), 7.98 - 7.94 (m, 1 H), 7.70 - 7.64 (m, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.29 (t, J = 4.9 Hz, 1 H), 4.48 (s, 2H), 2.48 (s, 3H); Rt: 5.81 min. HRMS m/z [M+H] + for C14H13N40S: 285.08046, found 285.08128.

Reference： [1]Kirby, Ilsa T.; Schultz, Carsten; Cohen, Michael S.; Arnold, Moriah R.; Vermehren-Schmaedick, Anke; Sreenivasan, Raashi; Kojic, Ana; Thorsell, Ann-Gerd; Karlberg, Tobias; Schüler, Herwig [Cell Chemical Biology, 2018, vol. 25, # 12, p. 1547 - 1553] Cohen, Michael; Kirby, Ilsa T.; Person, Ashley [2021, vol. 12, # 11, p. 1950 - 1957]
[2]Current Patent Assignee: OREGON HEALTH & SCIENCE UNIVERSITY - WO2020/46753, 2020, A1 Location in patent: Page/Page column 26; 27

5
[ 22223-49-0 ]
[ 107-14-2 ]
[ 848369-52-8 ]

Reference： [1],2018,vol. 25,p. 1547 - 1553

6
[ 4389-45-1 ]
[ 848369-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / 18 h / 90 °C 2: hydrogenchloride / 1,4-dioxane / 125 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sulfuric acid / 18 h / 90 °C 2: hydrogenchloride / water; 1,4-dioxane / 125 °C / Inert atmosphere

Reference： [1]Kirby, Ilsa T.; Schultz, Carsten; Cohen, Michael S.; Arnold, Moriah R.; Vermehren-Schmaedick, Anke; Sreenivasan, Raashi; Kojic, Ana; Thorsell, Ann-Gerd; Karlberg, Tobias; Schüler, Herwig [Cell Chemical Biology, 2018, vol. 25, # 12, p. 1547 - 1553]
[2]Cohen, Michael; Kirby, Ilsa T.; Person, Ashley [2021, vol. 12, # 11, p. 1950 - 1957]

7
[ 848369-52-8 ]
4-benzylamino-2-butene methyl carbonate [ No CAS ]
(R)-2-benzyl-10-methyl-4-vinyl-1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazolin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 95 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₃₁H₂₆NO₂P; potassium phosphate / 1,2-dichloro-ethane / 15 h / 50 °C / Sealed tube; Inert atmosphere

Reference： [1]Peng, Fei; Tian, Hua; Zhang, Pengxiang; Yang, Haijun; Fu, Hua [Organic and Biomolecular Chemistry, 2019, vol. 17, # 26, p. 6461 - 6464]

8
[ 848369-52-8 ]
4-benzylamino-2-butene methyl carbonate [ No CAS ]
(E)-4-(benzyl((8-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methyl)amino)but-2-en-1-yl methyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With N-ethyl-N,N-diisopropylamine In ethanol at 95℃; Inert atmosphere;

Reference： [1]Peng, Fei; Tian, Hua; Zhang, Pengxiang; Yang, Haijun; Fu, Hua [Organic and Biomolecular Chemistry, 2019, vol. 17, # 26, p. 6461 - 6464]

9
[ 848369-52-8 ]
C₂₄H₂₈N₄O₂S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere