1023595-17-6|(1H-Indazol-4-yl)boronic acid| Ambeed

Structure of 1023595-17-6

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Quality Control of [ 1023595-17-6 ] Purity: 97% SDS Specification

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Product Details of [ 1023595-17-6 ]

CAS No. :	1023595-17-6
Formula :	C₇H₇BN₂O₂
M.W :	161.95
SMILES Code :	OB(C1=CC=CC2=C1C=NN2)O
MDL No. :	MFCD09878901
InChI Key :	BGZZJZIZRARGGZ-UHFFFAOYSA-N
Pubchem ID :	44118310

Safety of [ 1023595-17-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1023595-17-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	3.0
Molar Refractivity	45.92
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	69.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.76
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.58
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.62
Solubility	3.86 mg/ml ; 0.0238 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.48
Solubility	5.36 mg/ml ; 0.0331 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.79
Solubility	2.62 mg/ml ; 0.0162 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.96 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.91

Application In Synthesis of [ 1023595-17-6 ]

* 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 [ 1023595-17-6 ]

[ 1023595-17-6 ] Synthesis Path-Downstream 1~35

1
[ 1023595-17-6 ]
[ 76-05-1 ]
C₂HF₃O₂*C₂₀H₁₉N₇OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 201Preparation of: EPO <DP n="226"/>A mixture of 4-indazole-boronic acid (17 mg, 0.07 mmol), (24 mg, 0.05 mmol), Pd(Ph3P)4, K2co3 (22 mg) in a 3:1 mixture of dioxane/H2O (1 ml_) was heated at 150 0C for 30 minutes by microwave. The mixture was cooled, concentrated and then treated with a 9:1 mixture of TFA/hfeO at rt for 2h and then concentrated. The residue was taken up into 3:1 mixture of DMSO/CH3CN and purified by preparative LC to provide the title compound as TFA salt. HPLC-MS RT= 1.72 minutes, mass calculated for formula C20Hi9N7OS 405.14, observed LCMS m/z 406.15 (M+H).

References: [1]Patent: WO2008/54702,2008,A1 .Location in patent: Page/Page column 224-225.

2
[ 1023595-17-6 ]
[ 1137278-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 150℃; for 0.25h;Microwave irradiation;	Example 72; 4-(5-(lH-indazol-4-yl)-2-(methylthio)thiazolo[4,5-d]pyrimidin-7- yl)morpholine 147[00404] 5-Chloro-7-morpholino-2-(thiazol-4-yl)thiazolo[4,5-d]pyrimidine , lH-indazol-4- yl-4-boronic acid (2.5 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were <n="100"/>slurried with equal parts IM potassium acetate (3 eq) and acetonitrile. The solution was microwaved at 150 C for 15 minutes. The solution filtered and the solution was dried in vacuo. The resulting residue was purified by reverse phase silica gel chromatography to give the product 147.

References: [1]Patent: WO2009/42607,2009,A1 .Location in patent: Page/Page column 98-99.

3
[ 1023595-17-6 ]
[ 1137278-66-0 ]
[ 1137278-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 130℃; for 0.633333h;Microwave irradiation;	5-Chloro-2-((4-methylsulfonylpiperazin- 1 -yl)methyl)-7-moipholinothiazolo[5,4- d]pyrimidine, lH-indazol-4-yl-4-boronic acid (1.2 eq), and trans- dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were combined in a solution of equal parts sodium carbonate aqueous solution (IM, 3 eq) and acetonitrile. The solution was microwaved at 1300C for eighteen minutes. An additional 0.1 equivalents of trans- dichlorobis(triphenylphosphine)palladium(II) was added and the solution was microwaved at130 0C for an additional twenty minutes. Acetonitrile was added and the solution was filtered.The organic layer was purified by reverse phase chromatography to give the off white solid of129.

References: [1]Patent: WO2009/42607,2009,A1 .Location in patent: Page/Page column 91.

4
[ 1023595-17-6 ]
[ 1137279-06-1 ]
[ 1137278-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 140℃; for 0.166667h;Microwave irradiation;	(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4- methylsulfonylpiperazin-l-yl)methanone, lH-indazol-4-yl-4-boronic acid (2.5 eq), and trans- dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts IM sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 140 C for 10 minutes. Water was added and the solution was filtered. The resulting precipitate was washed with methylene chloride and the organic layer was purified by silica gel chromatography followed by reverse phase silica gel chromatography to give the product 141.

References: [1]Patent: WO2009/42607,2009,A1 .Location in patent: Page/Page column 96.

5
[ 1023595-17-6 ]
[ 1220700-80-0 ]
[ 1220700-95-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 100℃; for 3h;Sealed tube;	Step i; A mixture of 57 (2.09 g, 5.00 mmol), 1 H-indazol-4-ylboronic acid (1.21 g, 7.50 mmol), Pd(PPh3^CI2 (213 mg, 0.30 mmol), and K2CO3 (2.07 g, 15.0 mmol) in dioxane/water (20/10 ml_) was bubbled with nitrogen for 5 minutes. The reaction mixture was then heated in a sealed tube at 100 C to give a brown solution, which turned to a gray suspension later. Heating was continued for 3 h. After cooling the mixture was diluted with water (50 ml_) and vigorously stirred. The solid was collected by vacuum-filtration and further dried to give 2.49 g (99%) of 89 as a yellow solid. 1H NMR (400 MHz, CDCI3) delta 1.48 (s, 9 H), 1.94 (d, J=6.32 Hz, 2 H), 2.84 (br s, 4 H), 3.63 (s, 3 H), 4.31 (br s, 2 H), 6.33 (br s, 1 H), 7.56 - 7.63 (m, 1 H), 7.64 - 7.70 (m, 1 H), 7.74 (d, J=7.07 Hz, 1 H), 8.12 (d, J=8.84 Hz, 1 H), 8.45 - 8.66 (m, 2 H), 8.78 (s, 1 H), 10.44 (br s, 1 H).

References: [1]Patent: WO2010/38165,2010,A1 .Location in patent: Page/Page column 107.

6
[ 1023595-17-6 ]
[ 1220700-99-1 ]
[ 1220699-09-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 90℃;Sealed tube;	Step 3; A mixture of 1 -(1-acetylpiperidin-4-yl)-8-chloro-3-methyl-1 /-/-imidazo[4,5- c][1 ,5]naphthyridin-2(3H)-one (93) (540 mg, 1.50 mmol), 1 H-indazol-4-ylboronic acid (364 mg, 2.25 mmol), Pd(PPh3)2CI2 (74.4 mg, 0.105 mmol), and K2CO3 (622 mg, 4.50 mmol) in dioxane/water (8/4 ml_) was bubbled with nitrogen for 5 minutes, and heated in a sealed tube at 90 C overnight. After cooling the reaction mixture was partitioned between water (40 ml_) and CH2CI2/MeOH (100/5 ml_). The aqueous layer was further extracted with CH2CI2 (50 ml_). The organic extract was washed with brine, dried over sodium sulfate, and concentrated to give a waxy, yellow solid, which was purified on ISCO purification system with a 40-gram column using 0 - 10% MeOH in CH2CI2 to afford 450 mg (68%) of the title compound 254 as a waxy, pale yellow solid. 1H NMR (400 MHz, CDCI3) delta 1.88 - 2.04 (m, 2 H), 2.08 (br s, 3 H), 2.62 (t, J=12.51 Hz, 1 H), 2.82 (br s, 1 H), 3.02 (br s, 1 H), 3.24 (t, J=12.25 Hz, 1 H), 3.64 (s, 3 H), 3.95 (d, J=13.14 Hz, 1 H), 4.85 (d, J=12.88 Hz, 1 H), 6.28 (br s, 1 H), 7.54 - 7.64 (m, 1 H), 7.70 (t, J=7.20 Hz, 2 H), 8.12 (d, J=8.84 Hz, 1 H), 8.56 (d, J=8.84 Hz, 2 H), 8.79 (s, 1 H), 11.02 (br s, 1 H).

References: [1]Patent: WO2010/38165,2010,A1 .Location in patent: Page/Page column 110.

7
[ 1023595-17-6 ]
[ 1220113-84-7 ]
methyl 2-(1H-indazol-4-yl)-8-thiomethyl-4-morpholin-4-yl-pyrido[3,2-d]pyrimidine-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 12h;	Intermediate 22: Methyl 2-(1 H-lndazol-4-yl)-8-thiomethyl-4-morpholin-4-yl-pyridor3,2- dlpyrimidine-6-carboxylateA suspension of Example 2 (200 mg; 0.56 mmol), <strong>[1023595-17-6]indazole-4-boronic acid</strong> (180 mg; 1.12 mmol), Pd(PPh3)4 (64 mg; 0.06 mmol), sodium carbonate (170 mg; 1.6 mmol) in dioxane (12 ml.) and water (12 mL) was stirred at 900C for 12 hours, filtered through a short plug of Celite then concentrated in vacuo to afford the title compound as a yellow solid which was used without further purification. HPLC (Method C): RT 2.47 min (purity 68%). MS (ES+): 437.0.

References: [1]Patent: WO2010/37765,2010,A2 .Location in patent: Page/Page column 67-68.

8
[ 1023595-17-6 ]
[ 1268849-99-5 ]
[ 1268850-20-9 ]

Yield	Reaction Conditions	Operation in experiment
19%	With PdPCy3; sodium carbonate; In 1,2-dimethoxyethane; water; at 150℃; for 0.5h;Inert atmosphere; Microwave irradiation;	General procedure: The chloropyrimidine (1.0 equiv), boronic acid or ester (2.2 equiv), Bedford catalyst 29 (0.05 equiv) and 2 M aqueous Na2CO3 (2.2 equiv) were dissolved in 1,2-DME. The solution was degassed and backfilled with nitrogen, then stirred with microwave heating at 150 C for 30 min. The reaction mixture was cooled, absorbed onto a plug of silica (100 mg) and eluted (CHCl3/MeOH, 9:1). The crude product was obtained by evaporating the filtrate in vacuo and purified by one of the following methods:Method A: The crude compound was dissolved in methanol and purified using an SCX-2 ion exchange column, eluting first with MeOH, then 2 M NH3 in MeOH.Method B: Purification by preparative TLC using the specified eluent.Method C: Recrystallisation from MeOH/CHCl3/hexane, 1:1:4.