[ CAS No. 902148-83-8 ]

Name: 902148-83-8|(2-Hydroxypyridin-4-yl)boronic acid|98+%
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SKU: A738644
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Quality Control of [ 902148-83-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 902148-83-8 ]

SDS Specification

Alternatived Products of [ 902148-83-8 ]

Product Details of [ 902148-83-8 ]

CAS No. :	902148-83-8	MDL No. :	MFCD11223187
Formula :	C₅H₆BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JCYJDDDSHUVYNE-UHFFFAOYSA-N
M.W :	138.92 g/mol	Pubchem ID :	23546917
Synonyms :

Calculated chemistry of [ 902148-83-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	36.09
TPSA :	73.58 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) :	-7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.27
Log Po/w (WLOGP) :	-1.53
Log Po/w (MLOGP) :	-1.57
Log Po/w (SILICOS-IT) :	-1.62
Consensus Log Po/w :	-1.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.91
Solubility :	17.1 mg/ml ; 0.123 mol/l
Class :	Very soluble
Log S (Ali) :	-0.82
Solubility :	21.2 mg/ml ; 0.153 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.31
Solubility :	67.7 mg/ml ; 0.488 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 902148-83-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 902148-83-8 ]

* 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 [ 902148-83-8 ]

[ 902148-83-8 ] Synthesis Path-Downstream 1~4

1
[ 902148-83-8 ]
C₂₉H₂₀BrN₃ [ No CAS ]
C₃₄H₂₄N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 120℃; for 6h;	17.A To a mixture of degassed 1 ,4-dioxane (13 mL) and water (3 mL) in a microwave vial was added [1 ,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (0.026 g, 0.03 mmol), followed by the title compound from Preparative Example B (0.3 g, 0.612 mmol), (2-hydroxypyridin-4-yl)boronic acid (0.104 g, 0.75 mmol) and cesium carbonate (0.408 g, 1.15 mmol). The reaction mixture was then heated at ~120°C in a sand-bath for 6 hours. The reaction mixture was diluted with ethyl acetate (120 mL) and water (45 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford unreacted starting material B as off-white solid (0.1398 g, 47%). The gradient was then changed to dichloromethane/methanol (100/0 -> 95/5 -> 90/10 -> 80/20 -> 80/20) to afford the title compound as grey solid (0.0996 g, 32 %). 1H-NMR (400 MHz, DMSO-d6) δ = 11.52 (br-s, 1H), 9.43 (s, 1 H), 8.70 (d, 1 H), 8.23 (d, 1H), 7.97 (d, 1 H), 7.59-7.53 (m, 6H), 7.32-7.21 (m, 10H), 6.67 (d, 1H), 6.48 (d, 1 H), 6.19 (dd, 1 H) MS (ESI): m/z = 505.28 [M+Hf.

Reference： [1]Current Patent Assignee: AC IMMUNE SA; LIFE HEALTHCARE GROUP HOLDINGS (PTY) LTD - WO2018/15549, 2018, A1 Location in patent: Page/Page column 48; 49

2
[ 902148-83-8 ]
N-[(1R)-1-(3-bromophenyl)ethyl]-6,7-dimethoxy-2-methylquinazolin-4-amine [ No CAS ]
4-(3-{(1R)-1-[(6,7-dimethoxy-2-methylquinazolin-4-yl)amino]ethyl}phenyl)pyridin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With potassium phosphate; RuPhos precatalyst chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) In water; N,N-dimethyl-formamide at 75℃;	388 Example 388 4-(3-{(1R)-1-[(6-dimethoxy-2-methylquinazolin-4-yl)amino]ethyl}phenyl)pyridin-2-ol General procedure: To a solution of 2-hydroxypyridine-4-boronic acid (46.8 mg, 0.32 mmol) and N-[(1 R)-1 -(3- bromophenyl)ethyl]-6,7-dimethoxy-2-methylquinazolin-4-amine (described in example 191, 100 mg, 0.25 mmol) in DMF (10 mL) were added potassium phosphate solution (0.5 M in water, 1.49 mL) and the second generation RuPhos precatalyst (chloro(2- dicyclohexylphosphino-2',6'-diisopropoxy-1,1 '-biphenyl)[2-(2'-amino-1,1 '- biphenyl)]palladium(ll), 38.6 mg, 0.05 mmol). The reaction mixture was stirred at 75°C for two hours. More 2-hydroxypyridine-4-boronic acid (46.8 mg, 0.32 mmol), chloro(2- dicyclohexylphosphino-2',6'-diisopropoxy-1,1 '-biphenyl)[2-(2'-amino-1,1 '- biphenyl)]palladium(ll) (38.6 mg, 0.05 mmol) and potassium phosphate solution (0.5 M in water, 1.49 mL) were added and the reaction was stirred at 75°C overnight. The reaction mixture was filtered and the filtrate was evaporated. The title compound was obtained in 12% yield (12.4 mg) after HPLC chromatography. 1H-NMR (400 MHz, DMSO-d6): δ [ppm] = 12.07- 1 1.09 (m, 1H), 8.02 (d, 1H), 7.78 (s, 1H), 7.70 (s, 1H), 7.58-7.49 (m, 2H), 7.48-7.38 (m, 2H), 7.02 (s, 1H), 6.56 (d, 1H), 6.47 (dd, 1H), 5.69 (t, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 2.39-2.28 (m, 3H), 1.63 (d, 3H). LC-MS (Method 8): m/z: [M+H]+ = 417, Rt = 0.78 min.

Reference： [1]Current Patent Assignee: BAYER AG - WO2018/172250, 2018, A1 Location in patent: Page/Page column 323-324

3
[ 902148-83-8 ]
(2-chloro-quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone [ No CAS ]
(2-(2-hydroxypyridin-4-yl)quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 2h; Microwave irradiation;	2 Example 2: Synthesis of (2-(2-hydroxypyridin-4-yl)quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone 2-Hydroxypyridine-4-boronic acid (14.17 mmol), compound 4 (4.19 g, 12.98 mmol), Na2CO3 (4.51 g, 42.51 mmol), DME (22.95 mL) and H2O (5.67 mL) were added to a 50 mL microwave vial. The vial was degassed with N2 for 45 minutes. Then PdCl 2 (dppf) CH 2 Cl 2 (1.25 g, 1.70 mmol) adduct was added. The reaction mixture was heated at 120 ° C for 2 hours by microwave irradiation. The resulting mixture was diluted with ethyl acetate and filtered over EtOAc. It was then concentrated in vacuo. Purified by rapid chromatography, Using 0-100% ethyl acetate / heptane as eluent, Obtained as a white solid (2-(2-hydroxypyridin-4-yl)quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone, 4.31 g, yield 87 %.

Reference： [1]Current Patent Assignee: Wang Ping - CN108947969, 2018, A Location in patent: Paragraph 0034-0036

4
[ 902148-83-8 ]
3-chloro-6-({1-[4-(difluoromethyl)phenyl]-4-methyl-1H-1,2,3-triazol-5-yl}methoxy)pyridazine [ No CAS ]
4-[6-({1-[4-(difluoromethyl)phenyl]-4-methyl-1H-1,2,3-triazol-5-yl}methoxy)pyridazin-3-yl]pyridin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4 mg	With methanol; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 120℃; for 2h; Inert atmosphere;	2 4-[6-({1-[4-(difluoromethyl)phenyl]-4-methyl-1H-1,2,3-triazol-5-yl}methoxy)pyridazin-3-yl]pyridin-2-ol To (2-hydroxypyridin-4-yl)boronic acid (35 mg, 0.150 mmol) is added a solution of Example III.1 (37 mg, 0.100 mmol) in 0.5 mL methanol, 1 mL 1,4 dioxane, 2M aq sodium carbonate solution (0.10 ml, 0.200 mmol) and Pd-PEPPSI (1.68 mg 0.002 mmol) under argon and the reaction mixture is stirred for 2 h at 120° C. The mixture is purified by preparative HPLC to yield 4 mg of the product. ESI-MS: 411 [M+H]+

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2020/24261, 2020, A1 Location in patent: Paragraph 0219-0222

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[ CAS No. 902148-83-8 ]

Quality Control of [ 902148-83-8 ]

Related Doc. of [ 902148-83-8 ]

Product Details of [ 902148-83-8 ]

Calculated chemistry of [ 902148-83-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 902148-83-8 ]

Application In Synthesis of [ 902148-83-8 ]

[ 902148-83-8 ] Synthesis Path-Downstream 1~4

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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