1201645-46-6|N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide| Ambeed

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Quality Control of [ 1201645-46-6 ] Purity: 95% SDS Specification

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Product Details of [ 1201645-46-6 ]

CAS No. :	1201645-46-6
Formula :	C₁₃H₁₉BN₂O₃
M.W :	262.11
SMILES Code :	CC(=O)NC1=CC(=CN=C1)B1OC(C)(C)C(C)(C)O1
MDL No. :	MFCD11878288
InChI Key :	ADPVUZOCOXRLMP-UHFFFAOYSA-N
Pubchem ID :	57415705

Safety of [ 1201645-46-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 1201645-46-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	6
Fraction Csp3	0.54
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	75.03
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	60.45 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	1.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.15
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.	0.04
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	0.91
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.14
Solubility	1.91 mg/ml ; 0.00729 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.87
Solubility	3.55 mg/ml ; 0.0135 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	-4.01
Solubility	0.0254 mg/ml ; 0.0000968 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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.	-7.18 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	0.0
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<0.0
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)	2.97

Application In Synthesis of [ 1201645-46-6 ]

* 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 [ 1201645-46-6 ]

[ 1201645-46-6 ] Synthesis Path-Downstream 1~15

1
[ 15862-46-1 ]
[ 73183-34-3 ]
[ 1201645-46-6 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100.0℃;Inert atmosphere; Industrial scale;	A 1 L four-necked flask equipped with a magnetic stirrer, a thermometer, a reflux condenser and a bubbler was charged(0.23 mol) of 3-acetylamino-5-bromopyridine, 58.42 g (0.23 mol) of bis (pinacolato) diboron and 67.62 g (0.69 mol) of potassium acetate were added and 450 mL of dioxane was added. Under protection, 3.80 g (0.0051 mol) of ferrocenepalladium chloride was added, and the reaction was heated to 100 C. for 18-24 hours,TLC control to the end of the reaction, the temperature was precipitated solid, beating filtration, methanol was added 500mL dissolved, filtered and evaporated to dryness, add heptane beating, to give the product 55.40g, yield 92.1%.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100.0℃; for 1.0h;Sealed tube; Microwave irradiation;	Intermediate 61 : N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide To a suspension of A/-(5-bromopyridin-3-yl)acetamide (for a preparation see Intermediate 60, 563 mg, 2.62 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (1330 mg, 5.24 mmol) and potassium acetate (771 mg, 7.85 mmol) in 1 ,4-dioxane (8 mL) in a microwave vial, was added PdC idppf) (192 mg, 0.262 mmol). The vial was sealed and the mixture was heated in a microwave at 100C for 1 h. The mixture was dissolved in ethyl acetate and filtered through a Celite cartridge (10 g). The solvent was evaporated under reduced pressure to give A/-(5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)pyridin-3-yl)acetamide as a brown oil (1.77 g, 258 %). This crude material was used in the next step without further purification: 100 % conversion assumed therefore maximum purity of crude material is 39 %. LCMS (2 min, High pH): Rt = 0.47 min, MH+ 263
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 85.0℃; for 8.0h;Inert atmosphere;	To a 25 mL round-bottom flask was charged with N-(5-bromopyridin-3-yl)acetamide (500 mg, leq), Bis(pinacolato)diboron (l. leq), PdCl2(dppf) (0.05eq), AcOK (3eq) in 15 mL of dioxane. The mixture was thoroughly degassed by alternately connecting the flask to vacuum and nitrogen. The solution was heated at 85 0C for 8 h. The solvent was removed in vacauo to afford a mixture containing N-(5-(4,4,5,5-tetramethyl -l,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide. To the mixture, compound 43 (leq . 2 M K2CO3 (5 eq) and Pd(PPh3)4 (10 mg) and DMF (1OmL) was added. The reaction mixture was stirred at 155 0C for 8h under N2 protection. The mixture was diluted with water (10 mL) and extracted with DCM (3 X 20 mL). Organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give compound 44 (377 mg, 65%(two step)). 394. 1H-NMR: (delta, ppm, CDC13, 400MHz): 10.33 (s, IH), 9.50 (s, IH), 8.86 (s, IH), 8.78-8.75 (m, 3H), 8.45 (s, IH), 8.24-8.22 (d, IH), 7.94-7.91 (d, IH), 7.32-7.27 (m, 5H), 5.92 (s, 2H), 2.11 (s, 3H).

References: [1]Patent: CN103601745,2017,B .Location in patent: Paragraph 0037; 0038.
[2]Patent: WO2014/140077,2014,A1 .Location in patent: Page/Page column 55-56.
[3]Patent: WO2009/155527,2009,A2 .Location in patent: Page/Page column 254.

2
[ 1201645-46-6 ]
[ 1201646-55-0 ]
[ 1201646-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 155.0℃; for 8.0h;Inert atmosphere;	To a 25 mL round-bottom flask was charged with N-(5-bromopyridin-3-yl)acetamide (500 mg, leq), Bis(pinacolato)diboron (l. leq), PdCl2(dppf) (0.05eq), AcOK (3eq) in 15 mL of dioxane. The mixture was thoroughly degassed by alternately connecting the flask to vacuum and nitrogen. The solution was heated at 85 0C for 8 h. The solvent was removed in vacauo to afford a mixture containing N-(5-(4,4,5,5-tetramethyl -l,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide. To the mixture, compound 43 (leq . 2 M K2CO3 (5 eq) and Pd(PPh3)4 (10 mg) and DMF (1OmL) was added. The reaction mixture was stirred at 155 0C for 8h under N2 protection. The mixture was diluted with water (10 mL) and extracted with DCM (3 X 20 mL). Organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give compound 44 (377 mg, 65%(two step)). 394. 1H-NMR: (delta, ppm, CDC13, 400MHz): 10.33 (s, IH), 9.50 (s, IH), 8.86 (s, IH), 8.78-8.75 (m, 3H), 8.45 (s, IH), 8.24-8.22 (d, IH), 7.94-7.91 (d, IH), 7.32-7.27 (m, 5H), 5.92 (s, 2H), 2.11 (s, 3H).

References: [1]Patent: WO2009/155527,2009,A2 .Location in patent: Page/Page column 254.

3
[ 1201645-46-6 ]
[ 1201646-56-1 ]
[ 1201646-59-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 155.0℃; for 8.0h;Inert atmosphere;	To a 25 mL round-bottom flask was charged N-(5-bromopyridin-3-yl)aeetamide (500 mg leq), bis(pinacolato)diboron (l. leq), PdCl2(dppf) (0.05eq), AcOK (3eq) in 15 mL of dioxane. The mixture was thoroughly degassed by alternately connecting the flask to vacuum and nitrogen. The solution was heated at 85 0C for 8 h. The solvent was removed in vacauo. To the mixture compound 43' (leq), 2 M K2CO3 (5 eq) and PdCl2(dppf) (10 mg) and DMF (1OmL) was added. The reaction mixture was stirred at 155 0C for 8h under N2 protection. The mixture was diluted with water (10 mL) and extracted with DCM (3 X 20 mL). Organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give compound 48 (226 mg, 65% for two steps). MS (m/z) (M +H): 394. H- NMR: (delta, CDCl3, 400MHz, ppm): 9.34 (s, IH), 8.70 (s, IH), 8.59 (s, IH), 8.49 (s, IH), 8.32 (s, IH), 8.19 (m, 2H), 7.81 (d, IH), 7.41-7.36 (m, 5H), 5.69 (s, 2H), 2.27 (s, 3H).

References: [1]Patent: WO2009/155527,2009,A2 .Location in patent: Page/Page column 255.

4
[ 13535-01-8 ]
[ 1201645-46-6 ]

References: [1]Patent: WO2014/140077,2014,A1 .

5
[ 1201645-46-6 ]
(R)-7-bromo-5-methyl-2-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)furo[3,2-c]pyridin-4(5H)-one [ No CAS ]
(R)-N-(5-(5-methyl-2-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)-4-oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5.9 mg	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; at 120.0℃; for 2.0h;Microwave irradiation; Sealed tube;	To a stirred suspension of (R)-7-bromo-5-methyl-2-((2-methyl-4-(methylsulfonyl)piperazin-1- yl)methyl)furo[3,2-c]pyridin-4(5H)-one (for a preparation see Intermediate 5, 100 mg, 0.239 mmol), A/-(5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide (for a preparation see Intermediate 61 , 258 mg, 39% w/w, 0.382 mmol), potassium carbonate (99 mg, 0.717 mmol) in 1 ,2- DME (3 imL) in a microwave vial, was added fefra/ /s(triphenylphosphine)palladium(0) (13.81 mg, 0.012 mmol). The microwave vial was sealed and heated in a microwave at 120C for 2 h. The mixture was dissolved in ethyl acetate and filtered through a Celite cartridge. The solvent was evaporated under reduced pressure and the residue was purified by MDAP. Appropriate fractions were combined and concentrated in vacuo. The residue was dissolved in methanol and eluted through an amino propyl cartridge (500 mg). Appropriate fractions were reduced in vacuo. The residue was combined with another batch of crude product which was prepared using the same conditions. The crude material was purified by MDAP. Appropriate fractions were combined and

References: [1]Patent: WO2014/140077,2014,A1 .Location in patent: Page/Page column 77.

6
[ 1201645-46-6 ]
6’-chloro-2‘-(2,6-difluoro-3,5-dimethoxyphenyl)-1‘,2‘-dihydro-3‘H-spiro[cyclopropane-1,4‘-[2,7]naphthyridin]-3‘-one [ No CAS ]
N-(5-(2‘-(2,6-difluoro-3,5-dimethoxyphenyl)-3‘-oxo-2‘,3‘-dihydro-1‘H-spiro[cyclopropane-1,4‘-[2,7]naphthyridine]-6’-yl)pyridin-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [1,1?-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II); sodium carbonate; In water; tert-butyl alcohol; at 90.0℃; for 2.0h;	[0187]A mixture of 6?-chloro-2?-(2,6-difluoro-3,5-dimethoxyphenyl)-1?,2?-dihydro-3?H- spiro[cyclopropane- 1 ,4?-[2,7]naphthyridinj -3-one (30.0 mg, 0.0788 mmol), (3- aminophenyl)boronic acid (12.9 mg, 0.0945 mmol), sodium carbonate (18.4 mg, 0.173 mmol), and [1,1 ?-bis(di-cyclohexylphosphino)ferrocenej dichloropalladium(II) (3.0 mg, 0. 0039 mmol) in tert-butyl alcohol (3.0 mL) / water (3.0 mL) was stirred and heated at 90C. After 2 hours, the reaction mixture was quenched with saturated aq. NH4C1, extracted with methylene chloride. The combined organic layers were dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. The crude product was used directly in the next step without further purification. LCMS calculated for C24H22F2N303 (M+H) m/z :438.2; Found: 438.1;[0190] This compound was prepared using procedures analogous to those for example 1, step7, with N-[5-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-3-ylj acetamide replacing(3-aminophenyl)boronic acid. LCMS calculated for C25H23F2N404 [M+Hj m/z: 481.2;Found: 481.2.

References: [1]Patent: WO2016/134294,2016,A1 .Location in patent: Paragraph 0187; 0190.

7
[ 1201645-46-6 ]
N-(5-(3H-pyrazolo[3,4-c]quinolin-8-yl)pyridin-3-yl)acetamide [ No CAS ]