[ CAS No. 1201645-46-6 ] {[proInfo.proName]}

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Quality Control of [ 1201645-46-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1201645-46-6 ]

SDS Specification

Alternatived Products of [ 1201645-46-6 ]

Product Details of [ 1201645-46-6 ]

CAS No. :	1201645-46-6	MDL No. :	MFCD11878288
Formula :	C₁₃H₁₉BN₂O₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ADPVUZOCOXRLMP-UHFFFAOYSA-N
M.W :	262.11	Pubchem ID :	57415705
Synonyms :

Calculated chemistry of [ 1201645-46-6 ] Expand+

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 :	60.45 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.01
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.04
Log Po/w (SILICOS-IT) :	0.91
Consensus Log Po/w :	0.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.14
Solubility :	1.91 mg/ml ; 0.00729 mol/l
Class :	Soluble
Log S (Ali) :	-1.87
Solubility :	3.55 mg/ml ; 0.0135 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-4.01
Solubility :	0.0254 mg/ml ; 0.0000968 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.97

Safety of [ 1201645-46-6 ]

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

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 1~12

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).

Reference： [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).

Reference： [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).

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

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

Reference： [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

Reference： [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.

Reference： [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 ]