[ CAS No. 1201643-70-0 ] {[proInfo.proName]}

Name: 1201643-70-0|(1-Phenyl-1H-pyrazol-4-yl)boronic acid|98%
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SKU: A170628
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Quality Control of [ 1201643-70-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1201643-70-0 ]

Product Details of [ 1201643-70-0 ]

CAS No. :	1201643-70-0	MDL No. :	MFCD11044914
Formula :	C₉H₉BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YHFFOAKRWYIKBG-UHFFFAOYSA-N
M.W :	187.99	Pubchem ID :	43145398
Synonyms :

Calculated chemistry of [ 1201643-70-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	53.39
TPSA :	58.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.8
Log Po/w (WLOGP) :	-0.45
Log Po/w (MLOGP) :	0.0
Log Po/w (SILICOS-IT) :	-1.11
Consensus Log Po/w :	-0.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	2.07 mg/ml ; 0.011 mol/l
Class :	Very soluble
Log S (Ali) :	-1.61
Solubility :	4.67 mg/ml ; 0.0248 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.82
Solubility :	2.85 mg/ml ; 0.0152 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 1201643-70-0 ]

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 [ 1201643-70-0 ]

* 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.

Upstream synthesis route of [ 1201643-70-0 ]
Downstream synthetic route of [ 1201643-70-0 ]

[ 1201643-70-0 ] Synthesis Path-Upstream 1~2

1
[ 1002334-12-4 ]
[ 1201643-70-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium periodate; ammonium acetate In water; acetone at 20℃;	To the solution of 4-pinacolatoboron- 1 H-pyrazole (0.6 g, 3.1 mmol) in acetone/water (30 mL, v/v=l: l) was added NaIO₄ (2.0 g, 9.3 mmol) and NH₄OAc (0.54 g, 7.1 mmol). The reaction mixture was stirred overnight at room temperature. The result mixture was concentrated to give residues, purification by chromatography (MeOH:DCM=l :5) to give compound lH-pyrazol-4- ylboronic acid (0.3 g, 89percent) as light yellow solid. MS (m/z) (IVf +H): 189.

Reference： [1] Patent: WO2009/155527, 2009, A2, . Location in patent: Page/Page column 134-135

2
[ 15115-52-3 ]
[ 1201643-70-0 ]

Reference： [1] Patent: WO2009/155527, 2009, A2,

[ 1201643-70-0 ] Synthesis Path-Downstream 1~13

1
[ 1002334-12-4 ]
[ 1201643-70-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium periodate; ammonium acetate; In water; acetone; at 20℃;	To the solution of 4-pinacolatoboron- 1 H-pyrazole (0.6 g, 3.1 mmol) in acetone/water (30 mL, v/v=l: l) was added NaIO4 (2.0 g, 9.3 mmol) and NH4OAc (0.54 g, 7.1 mmol). The reaction mixture was stirred overnight at room temperature. The result mixture was concentrated to give residues, purification by chromatography (MeOH:DCM=l :5) to give compound lH-pyrazol-4- ylboronic acid (0.3 g, 89percent) as light yellow solid. MS (m/z) (IVf +H): 189.

Reference： [1]Patent: WO2009/155527,2009,A2 .Location in patent: Page/Page column 134-135

2
[ 1201643-70-0 ]
[ 1343461-08-4 ]
[ 1343461-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water;	Example 11 Synthetic route
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water;	Example 11 Synthetic route

Reference： [1]Patent: WO2011/130908,2011,A1 .Location in patent: Page/Page column 54-55
[2]Patent: WO2011/133444,2011,A1 .Location in patent: Page/Page column 53-54

3
[ 1201643-70-0 ]
[ 1343461-08-4 ]
[ 1343459-80-2 ]

Reference： [1]Patent: WO2011/130908,2011,A1

4
[ 1201643-70-0 ]
[ 1603136-55-5 ]
C₂₇H₂₈FN₅O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 65℃; for 4h;Inert atmosphere;	Step 1 To a set of 2-dram vials containing a stir bar was individually added the appropriate boronic acid/pinacol ester. To each vial was then added PdCl2(dppf)-CH2Cl2 adduct (6.78 mg, 8.30 muiotaetaomicron). The vials were transferred to a glove box under an atmosphere of nitrogen. To each vial was then added a solution of the triflate C14 (29 mg, 0.055 mmol) in dioxane (1 mL) followed by K2CO3 (1M, 0.166 mL, 0.166 mmol). The vials were capped and then removed from the glove bag and placed into a preheated aluminum block at 65 °C. The mixtures were stirred at that temperature for 4 hours. Step 2 To each vial was added water (2 mL) followed by DCM (2 mL). The mixtures were transferred to a Varian Bond Elute reservoir and the organic layer was drained into a set of 2- dram vials. To each of the aqueous layers was added additional DCM (1 mL). The organic layer was again drained into the set of 2-dram vials. The combined organic layers were concentrated in vacuo.

Reference： [1]Patent: WO2014/62549,2014,A1 .Location in patent: Page/Page column 75

5
[ 1201643-70-0 ]
[ 1603136-55-5 ]
[ 1603821-47-1 ]

Reference： [1]Patent: WO2014/62549,2014,A1

6
[ 1201643-70-0 ]
N-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-9-ethyl-8-iodo-9H-purin-6-amine trifluoroacetate [ No CAS ]
N-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-9-ethyl-8-(1-phenyl-1H-pyrazol-4-yl)-9H-purin-6-amine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; water; at 80℃; for 3h;Sealed tube; Inert atmosphere;	Step 4: Synthesis of N-(3-cyclopropyl-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl)-9-ethyl- 8-(l-phenyl-lH-pyrazol-4-yl)-9H-purin-6-amine (1-10)A vial was charged with (1 -phenyl- lH-pyrazol-4-yl)boronic acid (13.78 mg, 0.073 mmol), (S and R)-N-(3-cyclopropyl-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl)-9-ethyl-8-iodo-9H-purin-6- amine, TFA (22 mg, 0.039 mmol), PdCl2(dppf)-CH2Cl2 adduct (5.98 mg, 7.33 urnol), dioxane (400 mu) and Na2CC>3 (100 mu, 0.20 mmol, 2M aqueous solution). The vial was sealed and the mixture was evacuated and back filled with N2 (x 6), after which it was heated to 80°C for 3 h. The mixture was then cooled, filtered through a Whatman? Autovial? Syringeless Filter, PTFE; 0.45 mu, and purified by reverse-phase preparative HPLC (0: 100 to 95:5 MeCN:water: 0.1percent v/v TFA modifier) to afford (S and R)-N-(3-cyclopropyl-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl)-9-ethyl-8-(l-phenyl-lH- pyrazol-4-yl)-9H-purin-6-amine as the TFA salt (1-10) NMR (600 MHz, DMSO-d6) delta 9.02 (s, 1 H), 8.34-8.24 (m, 3 H), 7.93 (d, / = 7.8 Hz, 2 H), 7.53 (t, / = 7.2 Hz, 2 H),7.36 (t, / = 7.8 Hz, 1 H), 5.08-4.90 (m, 1 H), 4.54-4.46 (m, 1 H), 4.44 (q, / = 7.2 Hz, 2 H), 4.26-4.16 (m, 1 H), 3.16-3.00 (m, 2 H), 2.35-2.24 (m, 1 H), 2.22-2.06 (m, 2 H), 1.31 (t, / = 7.2 Hz, 3 H), 1.20-1.10 (m, 2 H), 1.10-0.94 (m, 2 H); MS (EI) Calc'd for C25H27N10 [M+H]+, 467; found 467.

Reference： [1]Patent: WO2015/188369,2015,A1 .Location in patent: Page/Page column 43; 44

7
[ 915019-50-0 ]
[ 1201643-70-0 ]
2-methyl-2-{4-[3-methyl-2-oxo-8-(1-phenyl-1H-pyrazol-4-yl)-1Η-2,3-dihydroimidazo[4,5-c]quinolin-1-yl]phenyl}propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.4%		To a 50 ml three-necked flask under nitrogen was added 0.5 g (1.2 mmol) of intermediate 9,0.03 g (0.036 mmol) of bis-diphenylphosphine palladium dichloride,5ml DMF, heated to 100 ° C reaction 2h.3 mL of a 21percent aqueous solution of potassium carbonate was added,A solution of 0.318 (1.56 mmol) of <strong>[1201643-70-0]1-phenyl-1H-pyrazole-4-boronic acid</strong> in DMF,The reaction was continued at 100 ° C for 3 h. After cooling to room temperature,(Eluent: methanol: dichloromethane = 1: 60, v: v) to give 0.47 g of the desired product of Example 2 as a white solid, which was purified by silica gel column chromatography , Yield 82.4percent

Reference： [1]Patent: CN104411706,2016,B .Location in patent: Paragraph 0215-0217

8
[ 1201643-70-0 ]
C₂₀H₂₂BN₃O₂ [ No CAS ]

Reference： [1]Patent: CN104411706,2016,B

9
[ 1201643-70-0 ]
2-methyl-2-{4-[3-methyl-2-oxo-8-[6-(1-phenyl-1-H-pyrazol-4-yl)pyridin-3-yl]-1Η-2,3-dihydroimidazo[4,5-c]quinolin-1-yl]phenyl}propionitrile [ No CAS ]

Reference： [1]Patent: CN104411706,2016,B

10
[ 1201643-70-0 ]
[ 223463-13-6 ]
C₁₄H₁₀BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		(3.5 mmol) of 2-iodo-5-bromothiopyridine was dissolved in 5 ml of 4-dioxane,0.128 (0.1 mole) of tetrakis (triphenylphosphine) palladium was added under nitrogen atmosphere,80 ° (reaction 211. To room temperature,Followed by the addition of 9 ml of a 21percent aqueous sodium carbonate solution,A solution of 0.8 g (4.2 mmol)1-Phenyl-1H-pyrazole-4-boronic acid in 1,4-dioxane5ml, rose to 100 ° CThe reaction was continued for 4 h.After cooling to room temperature, it was poured into ice water, solid precipitated, stirred until solid precipitated completely,The product was purified by silica gel column chromatography (eluent:Ethyl acetate / petroleum ether = l / lO, V: V) gave a white solid intermediate 10h 0.86 g, yield 82percent

Reference： [1]Patent: CN104411706,2016,B .Location in patent: Paragraph 0251-0254

11
[ 1201643-70-0 ]
C₃₀H₂₇BrN₄O₃ [ No CAS ]
C₃₉H₃₄N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		In a three-necked flask will be 1.5g(2.63 mmol) of Intermediate 18 was dissolved in 15 mL of DMF, evacuated under nitrogen, and added under vacuumTo 0.068 (0.08 mmol) of Pd (pph3) Cl2 (: 12 heated to 95 ° -100 ° (: reaction 2-3 h) 0.598 (3.16 mmol)(1-phenyl-1H-pyrazol-4-yl) boronic acid5.0 ml of DMF; 1.39 g (13. lmmol) of sodium carbonate was dissolved in 7.2 mL of water;The above twoA solution is added to the reaction flask,Heating at 110 ° C for 3 h. After completion of the reaction, the reaction solution was poured into ice water and stirred until the whole was solidThe crude product was purified by silica gel column chromatography (eluent: methanol / dichloromethane = 1/40, (V: V)) to give a white solidBody 19b 1.45 g, yield 87

Reference： [1]Patent: CN104411706,2016,B .Location in patent: Paragraph 0486-0487

12
[ 1201643-70-0 ]
C₁₅H₁₈BrN₃O₂ [ No CAS ]
(2S,3S,4S)-2-cyano-4-(hydroxymethyl)-3-(4-(1-phenyl-1H-pyrazol-4-yl)phenyl)-N-propylazetidine-1-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 438 - 442

13
[ 15115-52-3 ]
[ 1201643-70-0 ]

Reference： [1]Patent: WO2009/155527,2009,A2

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Ghs Precautionary Statements

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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
H205	May mass explode in fire
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

[ CAS No. 1201643-70-0 ] {[proInfo.proName]}

Quality Control of [ 1201643-70-0 ]

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Calculated chemistry of [ 1201643-70-0 ]

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Druglikeness

Water Solubility

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Application In Synthesis of [ 1201643-70-0 ]

[ 1201643-70-0 ] Synthesis Path-Upstream 1~2

[ 1201643-70-0 ] Synthesis Path-Downstream 1~13

Related Functional Groups of [ 1201643-70-0 ]

Organoboron

Aryls

Related Parent Nucleus of [ 1201643-70-0 ]

Pyrazoles

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[ 1201643-70-0 ]

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[ 1201643-70-0 ]