[ CAS No. 191089-06-2 ]

Name: 191089-06-2|4-Borono-2-methylbenzoic acid|98%
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Quality Control of [ 191089-06-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 191089-06-2 ]

Product Details of [ 191089-06-2 ]

CAS No. :	191089-06-2	MDL No. :	MFCD09037832
Formula :	C₈H₉BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JCNNWPPDDRQZJM-UHFFFAOYSA-N
M.W :	179.97 g/mol	Pubchem ID :	53216737
Synonyms :

Calculated chemistry of [ 191089-06-2 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	48.19
TPSA :	77.76 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) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.72
Log Po/w (WLOGP) :	-0.63
Log Po/w (MLOGP) :	0.2
Log Po/w (SILICOS-IT) :	-0.89
Consensus Log Po/w :	-0.12

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.62
Solubility :	4.33 mg/ml ; 0.024 mol/l
Class :	Very soluble
Log S (Ali) :	-1.93
Solubility :	2.11 mg/ml ; 0.0117 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.05
Solubility :	16.1 mg/ml ; 0.0895 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 191089-06-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 191089-06-2 ]

* 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.

Downstream synthetic route of [ 191089-06-2 ]

[ 191089-06-2 ] Synthesis Path-Downstream 1~20

1
[ 191089-06-2 ]
[ 455-14-1 ]
C₁₅H₁₃BF₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane

Reference： [1]Zheng, Xiaozhang; Hodgetts, Kevin J.; Brielmann, Harry; Hutchison, Alan; Burkamp, Frank; Brian Jones; Blurton, Peter; Clarkson, Robert; Chandrasekhar, Jayaraman; Bakthavatchalam, Rajagopal; De Lombaert, Stephane; Crandall, Marci; Cortright, Daniel; Blum, Charles A. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 5217 - 5221]

2
[ 191089-06-2 ]
2-methyl-4-(3-methyl-pyridin-2-yl)-<i>N</i>-(4-trifluoromethyl-phenyl)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: BOP / CH₂Cl₂ 2: aq. Na₂CO₃; Pd(PPh₃)4 / 1,2-dimethoxy-ethane / 80 °C

3
[ 5419-55-6 ]
[ 68837-59-2 ]
[ 191089-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Triisopropyl borate; 4-bromo-2-methylbenzoic acid With n-butyllithium In tetrahydrofuran Stage #2: In tetrahydrofuran Acidic conditions;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/63167, 2006, A1 Location in patent: Page/Page column 22

4
[ 191089-06-2 ]
[ 1899-24-7 ]
[ 1052597-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In methanol; water; toluene for 3h; Reflux;

Reference： [1]Location in patent: scheme or table Moreau; Desroy; Genevard; Vongsouthi; Gerusz; Le Fralliec; Oliveira; Floquet; Denis; Escaich; Wolf; Busemann; Aschenbrenner [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 14, p. 4022 - 4026]

5
[ 191089-06-2 ]
[ 947248-68-2 ]
[ 1309682-28-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methyl-4-p-carboxybenzeneboronic acid,; 6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine With potassium carbonate In propan-1-ol for 1h; Reflux; Stage #2: With hydrogenchloride In water	Int11.1 Intermediate [Example Intl 1.14- 2-amino[1 , 2, 4]triazolo[1 ,5-a] pyridin-6-yl)-2-methyl benzoic acidTo a stirred solution of Int1.2 (1 .45 g) in 1 -propanol (65 mL) was added 2M potassium carbonate solution (10 mL), 4-carboxy-3-methylphenylboronic aci (1 .22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1 H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).
	With potassium carbonate In propan-1-ol for 1h; Reflux;	Int05.01 Intermediate Example Int05.01; 4- 2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-2-methylbenzoic acid To a stirred solution of Int01.02 (1.45 g) in 1 -propanol (65 ml) was added 2M potassium carbonate solution (10 ml), 4-carboxy-3-methylphenylboronic acid (1.22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).
	Stage #1: 3-methyl-4-p-carboxybenzeneboronic acid,; 6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine With potassium carbonate In propan-1-ol for 1h; Reflux; Stage #2: With hydrogenchloride In water	Intermediate Example Int7.14- 2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-2-methylbenzoic acid To a stirred solution of Int 1.2 (1.45 g) in 1 -propanol (65 mL) was added 2M potassium carbonate solution (10 mL), 4-carboxy-3-methylphenylboronic acid (1.22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).

With potassium carbonate In propan-1-ol

05.01 Intermediate Example Int05.014- 2-amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-2-methylbenzoic acidTo a stirred solution of Int01.02 (1.45 g) in 1 -propanol (65 mL) was added 2M potassium carbonate solution (10 mL), 4-carboxy-3-methylphenylboronic acid (1 .22 g), triphenylphosphine (0.17 g) and PdCl2(PPh3)2 (0.35 g). The mixture was heated to reflux for 1 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). 1 N hydrochloric acid was added to the aqueous phase until pH 5 was reached. The precipitated solid was collected by filtration, was washed with water, ethanol and ether and was dried in vacuum to give 0.8 g of the title compound.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 2.57 (s, 3H), 6.37 (br. s., 2H), 7.52 (d, 1 H), 7.65 (dd, 1 H), 7.70 (s, 1 H), 7.89 (d, 1 H), 7.95 (dd, 1 H), 9.06 (d, 1 H), 12.87 (br. s., 1 H).

Reference： [1]Current Patent Assignee: BAYER AG - WO2011/64328, 2011, A1 Location in patent: Page/Page column 74-75
[2]Current Patent Assignee: BAYER AG - WO2011/157688, 2011, A1 Location in patent: Page/Page column 104
[3]Current Patent Assignee: BAYER AG - WO2012/143329, 2012, A1 Location in patent: Page/Page column 84-85
[4]Current Patent Assignee: BAYER AG - WO2012/160029, 2012, A1 Location in patent: Page/Page column 80-81

6
[ 191089-06-2 ]
[ 1082604-63-4 ]
[ 1464154-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;	74.1 Step 1 : To a solution of 4-(6-chloroimidazo[l,2-b]pyridazin-3-yl)benzonitrile (200 mg, 0.67 mmol) in a mixture of DMF (4 mL) and water (lmL) blanketed with nitrogen, was successively added K2C03 (185 mg, 1.34 mmol), Pd(dppf)Cl2 (98 mg, 0.13 mmol) and 4- borono-2-methylbenzoic acid (131 mg, 0.73 mmol). The reaction mixture was stirred at 80 °C for 18 h, then was diluted with water (10 mL) and extracted with DCM (3 χ 10 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the crude 4-(3-(4-cyanophenyl)imidazo[l,2-b]pyridazin-6-yl)-2- methylbenzoic acid (271 mg) as black solid which was used carried forth to the next step without further purification. MS (ESI) m/z 355 [C21Hi4FN402 + H ]+.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;	74.1 Example 74 To a solution of 4-(6-chloroimidazo[1,2-b]pyridazin-3-yl)benzonitrile (200 mg, 0.67 mmol) in a mixture of DMF (4 mL) and water (1 mL) blanketed with nitrogen, was successively added K2CO3 (185 mg, 1.34 mmol), Pd(dppf)Cl2 (98 mg, 0.13 mmol) and 4-borono-2-methylbenzoic acid (131 mg, 0.73 mmol). The reaction-mixture was stirred at 80° C. for 18 h, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude 4-(3-(4-cyanophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-methylbenzoic acid (271 mg) as black solid which was used carried forth to the next step without further purification. MS (ESI) m/z 355 [C21H14FN4O2+H]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2013/147711, 2013, A1 Location in patent: Page/Page column 149
[2]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - US2014/371199, 2014, A1 Location in patent: Paragraph 0556

7
[ 191089-06-2 ]
[ 1025065-97-7 ]
[ 1464155-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;	83.1 Step 1 : To a solution of 6-chloro-3-(4-chlorophenyl)imidazo[l,2-b]pyridazine (308 mg, 1.00 mmol) in a mixture of DMF (4 mL) and water (lmL), were successively added K CO3 (138 mg, 1.00 mmol), Pd(dppf)Cl2 (146 mg, 0.20 mmol) and 4-borono-2-methylbenzoic acid (198 mg, 1.10 mmol). The reaction mixture was stirred at 80 °C for 18 h under inert atmosphere, then was diluted with water (10 mL) and extracted with DCM (3x10 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under vacuum to afford the crude 4-(3-(4-chlorophenyl)imidazo[l,2-b]pyridazin-6-yl)-2-methylbenzoic acid (724 mg) as black solid. MS (ESI) m/z 364 [C20H14ClN3O2 + H ]+.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;	83.1 Example 83 To a solution of 6-chloro-3-(4-chlorophenyl)imidazo[1,2-b]pyridazine (308 mg, 1.00 mmol) in a mixture of DMF (4 mL) and water (1 mL), were successively added K2CO3 (138 mg, 1.00 mmol), Pd(dppf)Cl2 (146 mg, 0.20 mmol) and 4-borono-2-methylbenzoic acid (198 mg, 1.10 mmol). The reaction mixture was stirred at 80° C. for 18 h under inert atmosphere, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford the crude 4-(3-(4-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-methylbenzoic acid (724 mg) as black solid. MS (ESI) m/z 364 [C20H14ClN3O2+H]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2013/147711, 2013, A1 Location in patent: Page/Page column 161; 162
[2]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - US2014/371199, 2014, A1 Location in patent: Paragraph 0594

8
[ 191089-06-2 ]
[ 1464153-49-8 ]
[ 1464153-68-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide for 18h; Inert atmosphere; Reflux;	27.2 Example 27 4-borono-2-methylbenzoic acid (100 mg, 0.55 mmol), K2CO3 (138 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.1 mg, 0.01 mmol) were added sequentially to a solution of 4-(6-bromoimidazo[1,2-a]pyrazin-3-yl)benzonitrile (150 mg, 0.50 mmol) in DMF at room temperature under inert atmosphere. The reaction mixture was refluxed for 18 h, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford 4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-methylbenzoic acid (105 mg, 83%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) 12.87 (bs, 1H), 9.31 (s, 1H), 9.07 (s, 1H), 8.24 (s, 1H), 8.10-8.04 (m, 5H), 8.02 (d, J=8.2 Hz, 1H), 7.94 (d, J=8.2 Hz, 1H), 2.62 (s, 3H); MS (ESI) m/z 355 [C21H14N4O2+H]+.
105 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	27.2 Step 2: 4-borono-2-methylbenzoic acid (100 mg, 0.55 mmol), 2C03 (138 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.1 mg, 0.01 mmol) were added sequentially to a solution of 4-(6- bromoimidazo[l,2-a]pyrazin-3-yl)benzonitrile (150 mg, 0.50 mmol) in DMF at room temperature under inert atmosphere. The reaction mixture was refluxed for 18 h, then was diluted with water (10 mL) and extracted with DCM (3x10 mL). The combined organic layers were dried over Na S04, filtered and concentrated under reduced pressure to afford 4- (3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2-methylbenzoic acid (105 mg, 83 %) as a brown solid. 1H NMR (400 MHz, DMSO- 12.87 (bs, 1H), 9.31 (s, 1H), 9.07 (s, 1H), 8.24 (s, 1H), 8.10 - 8.04 (m, 5H), 8.02 (d, J= 8.2 Hz, 1H), 7.94 (d, J= 8.2 Hz, 1H), 2.62 (s, 3H); MS (ESI) m/z 355 [C21H14N402 + H ]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - US2014/371199, 2014, A1 Location in patent: Paragraph 0416
[2]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2013/147711, 2013, A1 Location in patent: Page/Page column 105

9
[ 191089-06-2 ]
[ 757978-19-1 ]
C₂₁H₁₅BrN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 105℃; for 72h;

Reference： [1]Price, Daniel J.; Drewry, David H.; Schaller, Lee T.; Thompson, Brian D.; Reid, Paul R.; Maloney, Patrick R.; Liang, Xi; Banker, Periette; Buckholz, Richard G.; Selley, Paula K.; McDonald, Octerloney B.; Smith, Jeffery L.; Shearer, Todd W.; Cox, Richard F.; Williams, Shawn P.; Reid, Robert A.; Tacconi, Stefano; Faggioni, Federico; Piubelli, Chiara; Sartori, Ilaria; Tessari, Michela; Wang, Tony Y. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1958 - 1963]

10
[ 191089-06-2 ]
2-methyl-4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 72 h / 105 °C 2: sodium carbonate; palladium dichloride / 1,4-dioxane / 15 h / 100 °C 3: potassium carbonate / methanol / 65 h / 50 °C

11
[ 191089-06-2 ]
C₂₇H₂₀N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 72 h / 105 °C 2: sodium carbonate; palladium dichloride / 1,4-dioxane / 15 h / 100 °C

12
[ 191089-06-2 ]
C₃₉H₃₆Br₃Cl₆N₆O₃ [ No CAS ]
C₆₃H₅₇Cl₆N₆O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With 2'-dicyclohexyl-2,6-dimethoxy-3-(sulfonic acid)-1,1'-biphenyl sodium; potassium carbonate; palladium dichloride In water at 100℃; for 36h; Schlenk technique; Inert atmosphere;	2.2 (2) Preparation of nitrite-containing aryltriphenyl (triazine) tricarboxylic acid (22) Under a protective atmosphere of inert gas (high purity nitrogen), 1 mmol of the nitrogen-containing oxygen radical-triarylbenzene (triazine) bromide (24) obtained in the step (1) is added to a 50 ml Schlek reaction tube, 6mmol 3-methyl-4-p-carboxybenzeneboronic acid, 0.15 mmol of palladium chloride, 0.18 mmol of 2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 6 mmol of potassium carbonate and 30 ml of water, The reaction tube was replaced with nitrogen three times, then heated to 100 ° C with an oil bath under magnetic stirring, and the reaction was refluxed for 36 h; The oil bath was removed, the reaction was filtered, the filtrate was acidified, the pH was adjusted to 1 with concentrated hydrochloric acid, and stirred at 20 ° C for 1 h, filtered, and dried. A pure product containing a nitroxyl radical, a ternary arylbenzene (triazine)tricarboxylic acid (22) was obtained, and the structural formula was as follows, and the yield was 66%.

Reference： [1]Current Patent Assignee: LUOYANG NORMAL UNIVERSITY - CN109053541, 2018, A Location in patent: Paragraph 0073; 0077-0079

13
[ 191089-06-2 ]
C₄₂H₄₈Br₃N₆O₃ [ No CAS ]
C₆₆H₆₉N₆O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 2'-dicyclohexyl-2,6-dimethoxy-3-(sulfonic acid)-1,1'-biphenyl sodium; potassium carbonate; palladium dichloride In water at 100℃; for 36h; Schlenk technique; Inert atmosphere;	6.2 (2) Preparation of nitrite-containing aryl benzene ((triazine)) tricarboxylic acid (29) Under the protection of inert gas (high purity nitrogen), add 1 mmol of the nitrogen-containing oxygen radical-triarylbenzene (triazine) bromide obtained in the step (1) to a 50 ml Schlek reaction tube, and 6 mmol 3-methyl-4. - p-carboxyphenylboronic acid, 0.15 mmol of palladium chloride, 0.22 mmol of 2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 6 mmol of potassium carbonate and 30 ml of water, The reaction tube was replaced with nitrogen three times, then heated to 100 ° C with an oil bath under magnetic stirring, and the reaction was refluxed for 36 h; The oil bath was removed, the reaction was filtered, the filtrate was acidified, the pH was adjusted to 1 with concentrated hydrochloric acid, and stirred at 25 ° C for 1 h, then filtered. The obtained solid was dried to obtain a pure product nitrogen-oxygen radical-containing ternary arylbenzene (triazine)tricarboxylic acid (29) having the structural formula shown below, and the yield was 76%.

Reference： [1]Current Patent Assignee: LUOYANG NORMAL UNIVERSITY - CN109053541, 2018, A Location in patent: Paragraph 0099; 0102-0104

14
[ 191089-06-2 ]
[ 506-59-2 ]
[4-(dimethylcarbamoyl)-3-methylphenyl]boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methyl-4-p-carboxybenzeneboronic acid, With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: N,N-dimethylammonium chloride In N,N-dimethyl-formamide at 20℃; for 3h;	10.1 Step 1: Intermediate 7 -- [4-(Dimethylcarbamoyl)-3-methyl-phenyl]boronic acid . [0457] 4-Carboxy-3-methylphenylboronic acid (500 mg, 2.78 mmol) was dissolved in DMF (4 mL). DIPEA (2.9 mL, 16.67 mmol) and HATU (1.27 g, 3.33 mmol) were added and the resulting mixture was stirred at rt for 10 min. Dimethylamine HC1 (453 mg, 5.56 mmol) was added and the mixture stirred at rt for 3 h. Half-saturated aq. NH4CI (50 mL) and EtOAc (50 mL) were added, the organic layer was separated and the aqueous layer extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated to give the product (954 mg, 83%, 50% purity), which was used in the next step without further purification. MS ES+ m z 208 [M+H]+.

Reference： [1]Current Patent Assignee: HIBERCELL INC - WO2019/126731, 2019, A1 Location in patent: Paragraph 0457

15
[ 191089-06-2 ]
N,N,2-trimethyl-4-(6-(pyridin-3-ylamino)pyridin-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 3 h / 20 °C 2.1: potassium carbonate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / water; 1,2-dimethoxyethane / 0.67 h / 130 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: HIBERCELL INC - WO2019/126731, 2019, A1

16
[ 191089-06-2 ]
C₂₀H₂₄BrN₃O₂ [ No CAS ]
4-(6-amino-5-(((1S,2S)-2-((3,4-dimethylbenzyl)oxy)cyclopentyl)carbamoyl)pyridin-3-yl)-2-methylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane; water at 100℃; for 3h;

Reference： [1]Current Patent Assignee: DONG-A SOCIO HOLDINGS CO.,LTD. - WO2017/39331, 2017, A1 Location in patent: Paragraph 1388; 1390; 1395-1398; 1612-1615

17
[ 191089-06-2 ]
C₂₇H₃₄BrN₃O₂Si [ No CAS ]
C₃₅H₄₁N₃O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;

Reference： [1]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

18
[ 191089-06-2 ]
C₂₇H₃₁BrF₃N₃O₂Si [ No CAS ]
C₃₅H₃₈F₃N₃O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;

19
[ 191089-06-2 ]
4-((((1R,3R,5S)8-(5-bromopyridin-2-yl)-8-azabicyclo[3.2.1]oct-3-yl)oxy)methyl)-5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazole [ No CAS ]
4-(6-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]oct-8-yl)pyridin-3-yl)-2-methylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.1 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 8h;	5 Example 5: 4-(6-((1R,3r,5S)-3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl )Methoxy)-8-azabicyclo[3.2.1]oct-8-yl)pyridin-3-yl)-2-methylbenzoic acid (compound 5) Compound In-9 (160mg, 0.28mmol), 4-dihydroxyboryl-2-methylbenzoic acid (90mg, 0.34mmol), cesium carbonate (180mg, 0.56mmol), [1,1'-bis(two Phenylphosphino)ferrocene]palladium dichloride (20mg, 0.028mmol) was dissolved in 1,4-dioxane (5mL) and water (1mL), and reacted at 80°C for 8 hours. The reactant was cooled to room temperature, water was added, extracted with ethyl acetate, and the organic phase was dried over anhydrous sodium sulfate and concentrated. The residue after the reaction was concentrated was purified by silica gel column chromatography (PE/EA=1/1) to obtain a crude product, and the crude product was separated by Prep-HPLC to obtain the title compound 5 (2.1 mg).

Reference： [1]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN112812114, 2021, A Location in patent: Paragraph 0261-0265

20
[ 191089-06-2 ]
(4S,7R)-7-((S)-1-acetylpyrrolidine-2-carboxamido)-14-iodo-N,N-dimethyl-6,10-dioxo-1,3,4,5,6,7,8,10-octahydrobenzo[j][1,8,5]oxathiaazacyclododecine-4-carboxamide [ No CAS ]
4-((4S,7R)-7-((S)-1-acetylpyrrolidine-2-carboxamido)-4-(dimethylcarbamoyl)-6,10-dioxo-1,3,4,5,6,7,8,10-octahydrobenzo[j][1,8,5]oxathiaazacyclododecin-14-yl)-2-methylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In tetrahydrofuran; water at 65℃; for 4h; Sealed tube; Inert atmosphere;

Reference： [1]Begnini, Fabio; Geschwindner, Stefan; Johansson, Patrik; Wissler, Lisa; Lewis, Richard J.; Danelius, Emma; Luttens, Andreas; Matricon, Pierre; Carlsson, Jens; Lenders, Stijn; König, Beate; Friedel, Anna; Sjö, Peter; Schiesser, Stefan; Kihlberg, Jan [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 3473 - 3517]

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[ CAS No. 191089-06-2 ]

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Medicinal Chemistry

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[ 191089-06-2 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 191089-06-2 ]

Organoboron

Aryls

Carboxylic Acids

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[ 191089-06-2 ]