[ CAS No. 1151564-03-2 ] {[proInfo.proName]}

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2D 3D

Structure of 1151564-03-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1151564-03-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1151564-03-2 ]

SDS Specification

Alternatived Products of [ 1151564-03-2 ]

Product Details of [ 1151564-03-2 ]

CAS No. :	1151564-03-2	MDL No. :	MFCD07782041
Formula :	C₁₃H₁₈BClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVPMKYBFBINSHI-UHFFFAOYSA-N
M.W :	268.54	Pubchem ID :	45036907
Synonyms :

Calculated chemistry of [ 1151564-03-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	74.42
TPSA :	27.69 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.51
Log Po/w (WLOGP) :	2.65
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	2.5
Consensus Log Po/w :	2.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.83
Solubility :	0.0396 mg/ml ; 0.000148 mol/l
Class :	Soluble
Log S (Ali) :	-3.78
Solubility :	0.0451 mg/ml ; 0.000168 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.74
Solubility :	0.00488 mg/ml ; 0.0000182 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.01

Safety of [ 1151564-03-2 ]

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

Application In Synthesis of [ 1151564-03-2 ]

* 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 [ 1151564-03-2 ]
Downstream synthetic route of [ 1151564-03-2 ]

[ 1151564-03-2 ] Synthesis Path-Upstream 1~1

1
[ 1151564-17-8 ]
[ 77-78-1 ]
[ 1151564-03-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 28 - 55℃; for 0.666667 h;	To a stirred solution of 2-chloro-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2- yl)-phenol (830 g, 3.26 mol) in dry DMF (4.15 L) was added potassium carbonate(1126.4 g, 8.15 mol) under an inert atmosphere. Me2SO4 (402 mL, 4.24 mol) was added slowly to control the resulting exotherm (addition over 30 minutes gave a temperature rise from 28 0C to 55 0C) and after complete addition the reaction was stirred for 10 minutes. The reaction mixture was added to stirring HCl (5.98 L, 2 N, aq.) very slowly to control effervescence and the resulting precipitate stirred for 2 hours. The solids were filtered and washed with water (1 L) and dried in a vacuum oven over drying agent for 4 days to give 2-(2-chloro-3-methoxy-phenyl)-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane 7a as a white powder (746.7 g, 2.78 mol, 85 percent).

Reference： [1] Patent: WO2009/62087, 2009, A1, . Location in patent: Page/Page column 23

[ 1151564-03-2 ] Synthesis Path-Downstream 1~6

1
[ 1151564-17-8 ]
[ 77-78-1 ]
[ 1151564-03-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 28 - 55℃; for 0.666667h;	To a stirred solution of 2-chloro-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2- yl)-phenol (830 g, 3.26 mol) in dry DMF (4.15 L) was added potassium carbonate(1126.4 g, 8.15 mol) under an inert atmosphere. Me2SO4 (402 mL, 4.24 mol) was added slowly to control the resulting exotherm (addition over 30 minutes gave a temperature rise from 28 0C to 55 0C) and after complete addition the reaction was stirred for 10 minutes. The reaction mixture was added to stirring HCl (5.98 L, 2 N, aq.) very slowly to control effervescence and the resulting precipitate stirred for 2 hours. The solids were filtered and washed with water (1 L) and dried in a vacuum oven over drying agent for 4 days to give 2-(2-chloro-3-methoxy-phenyl)-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane 7a as a white powder (746.7 g, 2.78 mol, 85 %).

Reference： [1]Patent: WO2009/62087,2009,A1 .Location in patent: Page/Page column 23

2
[ 1151564-03-2 ]
[ 1150560-54-5 ]
[ 1150560-56-7 ]

Yield	Reaction Conditions	Operation in experiment
70%		Compound Ib (80 g, 0.19 mol), 7a (60.22 g, 0.22 mol), HP(^-Bu)3BF4 (13.01 g, 44.85 mmol), and Pd2(dba)3 (13.69 g, 14.95 mmol) were charged to the reaction vessel and purged with an inert atmosphere. Degassed THF (560 mL) was added followed by NaOH (31.45 g, 0.56 mol) in degassed water (128.8 mL) and the reaction warmed to 45 0C. After 2 hours acetic acid (56 mL) was added and stirred for 15 minutes. After settling, the layers were separated and the organic layer was filtered through celite, rinsing with hot THF (2 x 160 mL). The filtrate was concentrated in vacuo to a slurry, to which was added //-acetyl cysteine (15.84 g) as a solution in water (160 mL) and ethanol (640 mL) and stirred for 2 hours at 75 0C under an inert atmosphere. The slurry was cooled to RT, and the solids filtered off, washed with ethanohwater (8:2, 2 x 160 mL) to give 5-(2-chloro-3-methoxy-phenyl)-l-(2-fluoro-6-methyl-benzyl)-6-methyl-lH- pyrimidine-2,4-dione 7b as a white solid (58.6 g, 0.13 mol, 70 %).

Reference： [1]Patent: WO2009/62087,2009,A1 .Location in patent: Page/Page column 23, 24

3
[ 1780-26-3 ]
[ 1151564-03-2 ]
[ 1404109-75-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 90℃; for 15h;Sealed tube; Inert atmosphere;	00141 ] Example 1 : Synthesis of 3-] l-( {6-\|2-chloro-3-(methyloxy)phenyl]-2- mcthylpynmidin-4-yl}amino)ethyl] bcnzcncsulfonaniide (Compound 49) Step 1[00142] A pressure vessel was charged witli 4,6-dichloro-2-methyl-pyrimidine (1 .0g, 6.0 mmol. 1 .0 eq.), 2-(2-chloro-3-methoxyphenyl)-4.4.5,5-tetramethyl-[l ,3,2]dioxaborolane ( 1.6 g, 6.0 mmol, 1 .0 eq.), 1 ,2 DME ( 15 mL), and I Na2COj (2.0 mL). The reaction was purged with nitrogen before adding Pd(dppf)2Cl2CH2Cl2 (400 mg, 0.49 mmol, 0.08 eq.), then sealed and heated to 90 C for 15 hours. The reaction was then cooled to it and partitioned between water and EtOAc. The organic layer was dried with Na2S04 and concentrated under vacuum to give the crude product as a brown oil. The product was purified by Si02 flashchromatography (80:20 hexanes/ethyl acetate) to afford 4-chloro-6-(2-chloro-3- methoxyphenyl)-2-methylpyrimidine as a white solid (878 mg, 55% yield). NMR (400MHz, dfi-DMSO): 7.78 (s, 1 H), 7.46 (t, 1 H), 7.33 (d, 1H), 7.19 (d, 1 H), 3.88 (s, 3 H), 2.64 (s, 3H); MS (EI) for C \|2H ioCl2N20: 433.1 (MI-f).

Reference： [1]Patent: WO2012/149528,2012,A1 .Location in patent: Page/Page column 170--171

4
[ 1780-26-3 ]
[ 1151564-03-2 ]
[ 1404101-89-8 ]

Reference： [1]Patent: WO2012/149528,2012,A1

5
[ 1151564-03-2 ]
1-oxo-2-(pyrimidin-2-yl)-1,2,7,8-tetrahydrophthalazin-6-yl trifluoromethanesulfonate [ No CAS ]
6-(2-chloro-3-methoxyphenyl)-2-(pyrimidin-2-yl)-7,8-dihydrophthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; at 70℃; for 3h;Inert atmosphere;	General procedure: According to scheme 2, step viii: A mixture of intermediate 15a (200.00 mg, 518.07 umol, 1.00 eq), (2-methoxyphenyl)-boronic acid (157.45 mg, 1.04 mmol, 2.00 eq), Pd(PPh3)4 (119.73 mg, 103.61 umol, 0.20 eq), Na2CO3 (2 M, 1.17 mL, 4.50 eq) in THF (4.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70C for 3 hours under N2 atmosphere. The mixture was added water(20mL), extracted with AcOEt (20mLx3), the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (PE:EA=0:1) to give intermediate 16a (190.00 mg, crude) as a yellow oil.

Reference： [1]Patent: EP3459939,2019,A1 .Location in patent: Paragraph 0289; 0334

6
[ 1151564-03-2 ]
C₁₄H₁₁F₃N₄O₄S [ No CAS ]
6-(2-chloro-3-methoxyphenyl)-2-(5-methylpyrimidin-2-yl)-7,8-dihydrophthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.1%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; at 70℃; for 3h;Inert atmosphere;	General procedure: According to scheme 2, step viii: A mixture of intermediate 15a (200.00 mg, 518.07 umol, 1.00 eq), (2-methoxyphenyl)-boronic acid (157.45 mg, 1.04 mmol, 2.00 eq), Pd(PPh3)4 (119.73 mg, 103.61 umol, 0.20 eq), Na2CO3 (2 M, 1.17 mL, 4.50 eq) in THF (4.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70C for 3 hours under N2 atmosphere. The mixture was added water(20mL), extracted with AcOEt (20mLx3), the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (PE:EA=0:1) to give intermediate 16a (190.00 mg, crude) as a yellow oil.

Reference： [1]Patent: EP3459939,2019,A1 .Location in patent: Paragraph 0289; 0400

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Nomenclature of Ethers ? Preparation of Alkylbenzene ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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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. 1151564-03-2 ] {[proInfo.proName]}

Quality Control of [ 1151564-03-2 ]

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Calculated chemistry of [ 1151564-03-2 ] Expand+

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Medicinal Chemistry

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[ 1151564-03-2 ] Synthesis Path-Upstream 1~1

[ 1151564-03-2 ] Synthesis Path-Downstream 1~6

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Organoboron

Aryls

Chlorides

Ethers

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[ 1151564-03-2 ]