[ CAS No. 1201644-51-0 ] {[proInfo.proName]}

Name: 1201644-51-0|1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrrolidin-2-one|97%
Brand: Ambeed
SKU: A128118
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2D 3D

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Quality Control of [ 1201644-51-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1201644-51-0 ]

SDS Specification

Alternatived Products of [ 1201644-51-0 ]

Product Details of [ 1201644-51-0 ]

CAS No. :	1201644-51-0	MDL No. :	MFCD12032530
Formula :	C₁₅H₂₁BN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UCMAEVWLVAOKRQ-UHFFFAOYSA-N
M.W :	288.15	Pubchem ID :	45786487
Synonyms :

Calculated chemistry of [ 1201644-51-0 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.6
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	85.55
TPSA :	51.66 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.13
Log Po/w (MLOGP) :	0.96
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	1.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.71
Solubility :	0.557 mg/ml ; 0.00193 mol/l
Class :	Soluble
Log S (Ali) :	-2.3
Solubility :	1.46 mg/ml ; 0.00505 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.95
Solubility :	0.0322 mg/ml ; 0.000112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.96

Safety of [ 1201644-51-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1201644-51-0 ]

* 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 [ 1201644-51-0 ]

[ 1201644-51-0 ] Synthesis Path-Downstream 1~5

1
[ 928775-04-6 ]
[ 73183-34-3 ]
[ 1201644-51-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80.0℃;Inert atmosphere;	Intermediate 33 (214 mg, 0.89 mmol) was placed in a 10 mL flask. Bis(pinacolato)diborane (451 mg, 2.0 eq.) was added, followed by KOAc (261 mg, 3.0 eq.) and the catalyst (67 mg, 0.1 eq.). The flask was purged with N2 and DMSO (3 mL) was added. The mixture was degassed for 1 h before heating up to 80 C. and keeping this temperature o.n. The mixture was diluted with EtOAc and passed through a short Celite pad. The Celite was washed with EtOAc, and the filtrate was concentrated and washed with brine. The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by column (EtOAc/petroleum ether=1:3 to 1:1). The desired product (Intermediate 34) was obtained as a white solid (120 mg, 47%). 1HNMR (400 MHz, DMSO-d6, ppm): 8.57 (d, J=0.8 Hz, 1H); 8.33 (dd, J=8.4, 0.8 Hz, 1H); 8.00 (dd, J=8.4, 1.6 Hz, 1H); 4.00 (t, J=7.2 Hz, 2H); 2.60 (t, J=8.0 Hz, 2H); 2.05 (m, 2H), 1.31 (m, 12H).

Reference： [1]Patent: US2010/69441,2010,A1 .Location in patent: Page/Page column 36-37

2
[ 1217273-57-8 ]
[ 1201644-51-0 ]
[ 1217272-99-5 ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 70.0℃;Inert atmosphere;	Intermediate 34 (120 mg, 0.42 mmol) was mixed with Intermediate 18 (142 mg, 1.2 eq.), K2CO3 (115 mg, 2.0 eq.) and PdCl2(dppf)DCM (34 mg, 0.1 eq.). The flask was purged with N2, and 6 mL of 1,4-dioxane was added. The mixture was degassed for 1 h at r.t. and then heated at 70 C. o.n. The mixture was passed through a Celite pad and washed with EtOAc. The filtrate was concentrated and washed with brine. The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by column (EtOAc/petroleum ether=3:1 to 100% EtOAc). The desired product was obtained as a solid (50 mg, 33%). 1H NMR (400 MHz, DMSO-d6, ppm): δ 8.67 (d, J=2.0 Hz, 1H); 8.37 (d, J=8.8 Hz, 1H); 8.09 (dd, J=8.8, 2.8 Hz, 1H); 7.65 (s, 1H); 7.60 (d, J=8.0 Hz, 1H); 7.34 (d, J=8.0 Hz, 1H); 5.29 (s, 1H); 4.72 (m, 1H); 4.65 (dd, J=16.4, 9.2 Hz, 1H); 4.04 (t, J=7.2 Hz, 2H); 3.74 (m, 2H); 3.28 (m, 2H); 2.61 (t, J=8.0 Hz, 2H); 2.07 (m, 2H). MS (m/z): 366 [M+H].

Reference： [1]Patent: US2010/69441,2010,A1 .Location in patent: Page/Page column 36-37

3
[ 1201644-51-0 ]
[ 1354355-93-3 ]
[ 1354354-68-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 96.0℃;Inert atmosphere; Sealed tube;	[0224] Step 2: A mixture of 5-bromo-N-((2'-(trifluoromethyl)-[2,4'-bipyridin]-5- yl)methyl)picolinamide 72-1 (22 mg, 0.05 mmol), l-(5-(4,4,5,5-tetramethyl- l,3,2- dioxaborolan-2-yl)pyridin-2-yl)pyrrolidin-2-one 72-2 (29 mg, 0.1 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol) and K3P04 (21 mg, 0.1 mmol) in dioxane (0.5 mL) and water (0.1 mL) was stirred at 96 C under argon overnight. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate) and the filtrate was redistributed between ethyl acetate and water. The organic phase was dried over Na2S04 and concentrated with rotavap. The residue was subjected to preparative reverse phase HPLC separation to give 6'-(2- oxopyrrolidin-l-yl)-N-((2'-(trifluoromem^carboxamide 72 as a solid. MS m/z 519.2 (M + 1). 1H NMR 400 MHz (CDC13) δ 8.83 (d, 1 H), 8.79 (d, 1 H), 8.76 (dd, 1 H), 8.62 (dd, 1 H), 8.57 (dd, 1 H), 8.52 (t, 1 H), 8.34-8.29 (m, 2 H), 8.10-8.02 (m, 2 H), 7.96-7.88 (m, 2 H), 7.84 (d, 1 H), 4.79 (d, 2 H), 4.16 (t, 2 H), 2.71 (t, 2 H), 2.18 (t, 2 H).

Reference： [1]Patent: WO2012/3189,2012,A1 .Location in patent: Page/Page column 102-103

4
[ 1201644-51-0 ]
4-(5-chloro-8-[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile [ No CAS ]
4-{8-[(3R)-1-methylpiperidin-3-yl]methoxy}-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium(II); In 1,4-dioxane; water; at 90.0℃; for 3.0h;Inert atmosphere;	A mixture of 4-(5-chloro-8-[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile (47. mg, 0.12 mmol), potassium phosphate (78 mg, 0.37 mmol), dichloro[1,1'-bis(dicyclohexylphosphino)ferrocene]palladium(II) (9.3 g, 0.012 mmol), 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]pyrrolidin-2-one (JPM2 Pharma, cat No.JPM2-00-744: 42 mg, 0.15 mmol) in 1,4-dioxane (3 mL) and water (1 mL) was purged with nitrogen then stirred at 90 C. for 3 h. The reaction mixture was cooled to room temperature then extracted with DCM.

Reference： [1]Patent: US2016/9720,2016,A1 .Location in patent: Paragraph 0393

5
[ 1201644-51-0 ]
(S)-3-(7-chloro-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)-5-(difluoromethyl)-4-fluoro-N-methylbenzamide [ No CAS ]
(S)-3-(difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(2-oxopyrrolidin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate; In water; N,N-dimethyl-formamide; at 110.0℃; for 0.5h;	A sample of (S)-3-(7-chloro-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)-5-(difluoromethyl)-4-fluoro-N-methylbenzamide (15 mg, 0.034 mmol, see Example 26, Step 1) was dissolved in DMF (0.4 ml) and water (0.08 ml). This solution was treated with <strong>[1201644-51-0]1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrrolidin-2-one</strong> (29 mg, 0.10 mmol) and K2CO3 (14 mg, 0.10 mmol). Pd XPhos G2 (4 mg, 5 μmop was added, the vial was capped, and the solution was stirred at 110 C. After 30 mins, LCMS indicated consumption of the starting material. The solution was cooled to room temperature, diluted with MeCN and water, filtered through a SiliaPrep Thiol cartridge, and purified by HPLC (pH=2 method) to provide (S)-3-(difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(2-oxopyrrodin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide (1.7 mg, 3.0 μmol, 9% yield). LCMS calculated for C28H26F3N6O4 (M+H)+: m/z=567.2; found: 566.9.

Reference： [1]Patent: US2021/214366,2021,A1 .Location in patent: Paragraph 0687-0688

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H226	Flammable liquid and vapour
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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
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H301	Toxic if swallowed
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H310	Fatal in contact with skin
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H312	Harmful in contact with skin
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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
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H370	Causes damage to organs
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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

[ CAS No. 1201644-51-0 ] {[proInfo.proName]}

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Calculated chemistry of [ 1201644-51-0 ]

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Medicinal Chemistry

Safety of [ 1201644-51-0 ]

Application In Synthesis of [ 1201644-51-0 ]

[ 1201644-51-0 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 1201644-51-0 ]

Organoboron

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1201644-51-0 ]