[ CAS No. 1313738-80-5 ] {[proInfo.proName]}

Name: 1313738-80-5|1-Benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine|95%
Brand: Ambeed
SKU: A1145108
Rating: 90 (25 reviews)

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2D 3D

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Quality Control of [ 1313738-80-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1313738-80-5 ]

SDS Specification

Alternatived Products of [ 1313738-80-5 ]

Product Details of [ 1313738-80-5 ]

CAS No. :	1313738-80-5	MDL No. :	MFCD11840350
Formula :	C₁₈H₂₆BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UGTKSTXDPAFDOM-UHFFFAOYSA-N
M.W :	299.22	Pubchem ID :	49759215
Synonyms :

Calculated chemistry of [ 1313738-80-5 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	95.45
TPSA :	21.7 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.99
Log Po/w (WLOGP) :	2.92
Log Po/w (MLOGP) :	2.3
Log Po/w (SILICOS-IT) :	2.39
Consensus Log Po/w :	2.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.58
Solubility :	0.0782 mg/ml ; 0.000261 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.232 mg/ml ; 0.000777 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.87
Solubility :	0.00407 mg/ml ; 0.0000136 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.67

Safety of [ 1313738-80-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H413	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1313738-80-5 ]

* 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 [ 1313738-80-5 ]

[ 1313738-80-5 ] Synthesis Path-Downstream 1~19

1
[ 170161-34-9 ]
[ 73183-34-3 ]
[ 1313738-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80.0℃; for 4.0h;	Combine bis (pinacolato) diboron (0.437 g, 1.72 mmol), potassium acetate (0.454 g, 4.62 mmol), 1. 1'-bis (DIPHENYLPHOSPHINO) ferrocen (0.0273 g, 0.0492 mmol), [1, 1'- bis (DIPHENYLPHOSPHINO) FEN OCENE] dichloropalladium (II) complex with dichloromethane (0.0377 g, 0.0461 mmol), flush with nitrogen, treat with a solution of trifluoro- methanesulfonic acid 1-benzyl-1, 2,5, 6-tetrahydro-pyridin-3-yl ester (SEEZHENG, Q.; Yang, Y.; Martin, A. R. TETRAHEDRO7 Lett. 1993, 34, 2235-2238) (0.503 g, 1.56 mmol) in dioxane (10 mL), stir and heat at 80 C. After 4 h, concentrate the reaction mixture and dry in vacuo. Combine crude boronate, potassium carbonate (0.650 g, 4.70 mmol), [1, 1'- bis (diphenylphosphino) ferrocene] dichloropalladium (II) complex with dichloromethane (0.0777 g, 0.0951 mmol), treat with a solution of 6-(4-iodo-phenoxy)-nicotinamide (0.582 g, 1.71 mmol) in DIMETHYLFORMAMIDE (10 mL), stir and heat at 80 C. After 4.5 h, cool the reaction mixture to ambient temperature, dilute with water (30 mL), and extract with ethyl acetate (3 x 30 mL). Wash COMBINED ORGANIC EXTRACTS WITH BRINE (IX) dry NVER anhydrous magnesium sulfate, filter, and concentrate. Purify the residue by silica gel chromatography (10: 1 to 5: 1 ethyl acetate: methanol), then reverse-phase HPLC to provide 0.175 g (29%) of the title compound as a white solid: mass spectrum (electrospray) m/z = 386.2 (M+1) ; 1H NMR (methanol-d4) : 8.66 (d, 1H, J = 2.4 Hz), 8. 32 (dd, 1H, J = 2. 4,8. 3 Hz), 7.65-7. 52 (m, 5H), 7.52-7. 48 (m, 2H), 7.22 (d, 1H, J= 8.8 Hz), 7.10 (d, 1H, J = 8.8 Hz), 6.41 (m, 1H), 4.61 (d, 1H, J = 13.2 Hz), 4.52 (d, 1H,. 7= 12.7 HZ), 4.22-4. 20 (m, 2H), 3.72-3. 67 (m, 1H), 3.36-3. 31 (m, 1H), 2.75-2. 65 (m, 1H).

Reference： [1]Patent: WO2004/26305,2004,A1 .Location in patent: Page/Page column 179-180

2
[ 676495-46-8 ]
[ 1313738-80-5 ]
[ 676495-45-7 ]

Yield	Reaction Conditions	Operation in experiment
29%		Combine bis (pinacolato) diboron (0.437 g, 1.72 mmol), potassium acetate (0.454 g, 4.62 mmol), 1. 1'-bis (DIPHENYLPHOSPHINO) ferrocen (0.0273 g, 0.0492 mmol), [1, 1'- bis (DIPHENYLPHOSPHINO) FEN OCENE] dichloropalladium (II) complex with dichloromethane (0.0377 g, 0.0461 mmol), flush with nitrogen, treat with a solution of trifluoro- methanesulfonic acid 1-benzyl-1, 2,5, 6-tetrahydro-pyridin-3-yl ester (SEEZHENG, Q.; Yang, Y.; Martin, A. R. TETRAHEDRO7 Lett. 1993, 34, 2235-2238) (0.503 g, 1.56 mmol) in dioxane (10 mL), stir and heat at 80 C. After 4 h, concentrate the reaction mixture and dry in vacuo. Combine crude boronate, potassium carbonate (0.650 g, 4.70 mmol), [1, 1'- bis (diphenylphosphino) ferrocene] dichloropalladium (II) complex with dichloromethane (0.0777 g, 0.0951 mmol), treat with a solution of 6-(4-iodo-phenoxy)-nicotinamide (0.582 g, 1.71 mmol) in DIMETHYLFORMAMIDE (10 mL), stir and heat at 80 C. After 4.5 h, cool the reaction mixture to ambient temperature, dilute with water (30 mL), and extract with ethyl acetate (3 x 30 mL). Wash COMBINED ORGANIC EXTRACTS WITH BRINE (IX) dry NVER anhydrous magnesium sulfate, filter, and concentrate. Purify the residue by silica gel chromatography (10: 1 to 5: 1 ethyl acetate: methanol), then reverse-phase HPLC to provide 0.175 g (29%) of the title compound as a white solid: mass spectrum (electrospray) m/z = 386.2 (M+1) ; 1H NMR (methanol-d4) : 8.66 (d, 1H, J = 2.4 Hz), 8. 32 (dd, 1H, J = 2. 4,8. 3 Hz), 7.65-7. 52 (m, 5H), 7.52-7. 48 (m, 2H), 7.22 (d, 1H, J= 8.8 Hz), 7.10 (d, 1H, J = 8.8 Hz), 6.41 (m, 1H), 4.61 (d, 1H, J = 13.2 Hz), 4.52 (d, 1H,. 7= 12.7 HZ), 4.22-4. 20 (m, 2H), 3.72-3. 67 (m, 1H), 3.36-3. 31 (m, 1H), 2.75-2. 65 (m, 1H).

Reference： [1]Patent: WO2004/26305,2004,A1 .Location in patent: Page/Page column 179-180

3
[ 170161-34-9 ]
[ 73183-34-3 ]
[ 1313738-80-5 ]
[ 1401448-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80.0℃; for 3.0h;Inert atmosphere;	Step 3: (l-benzyl-3,6-dihydro-2H-pyridin-5-yl)boronic acid (47)Compound 45 (3.5 g, 10.89 mmol) was dissolved in 1,4-dioxane (45 mL) and potassium acetate (3.20 g, 32.67 mmol), 6z's pinacolanto)diorane (3.32 g, 13.07 mmol), 1,1- &/,y(diphenylphosphino) ferrocene-palladium(II)dichloride dichloromethane complex (0.355 g, 0.435 mmol) and l,l-bis(diphenylphosphino)ferrocene (0.241 g, 0.435 mmol) were added. The reaction mixture was degassed and purged with argon, followed by heating at 80 C for 3 h. The reaction mixture was allowed to cool to room temperature, filtered through celite pad, washed with ethyl acetate, concentrated and residue was used as such for next reaction (LCMS was showing formation of boronic acid 47 in major amount and respective boronate ester 46 as minor product)

Reference： [1]Patent: WO2012/127506,2012,A1 .Location in patent: Page/Page column 72

4
[ 40114-49-6 ]
[ 1313738-80-5 ]
[ 1401448-32-5 ]

Reference： [1]Patent: WO2012/127506,2012,A1

5
[ 50606-58-1 ]
[ 1313738-80-5 ]
[ 1401448-32-5 ]

Reference： [1]Patent: WO2012/127506,2012,A1

6
[ 1313738-80-5 ]
[ 65550-77-8 ]
2-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-5-chloro-3-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 110.0℃; for 0.5h;Inert atmosphere; Microwave irradiation; Sealed tube;	General procedure: A microwave vial was charged with i-benzyl-i,2,5,6-tetrahydropyridin-3-yl 1,1,2,2,3,3 ,4,4,4-nonafluorobutane- 1 -sulfonate (Intermediate 4; 0.986 g, 2.093 mmol), 1-methyl-2-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-indole (CAS 596819-10-2;0.565 g, 2.197 mmol) and potassium carbonate (0.868 g, 6.28 mmol) in dioxane (15 mL)/water (3.75 mL). The stirred mixture was degassed by bubbling nitrogen through it for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.121 g, 0.105 mmol) was added and the mixture was degas sed for another minute before being sealed and irradiated in amicrowave reactor at 100 C for 20 minutes. The reaction mixture was diluted with EtOAc and washed with water then brine and the organic part was loaded onto a pre-equilibrated cation exchange cartridge (SCX-2) and was eluted with EtOAc then EtOAc/[1M NH3 in MeOHj (4:1) and then EtOAc/[2M NH3 in MeOHj (4:1). The product containing fractions were combined and reduced in vacuo to afford the title compound.

Reference： [1]Patent: WO2015/79224,2015,A1 .Location in patent: Page/Page column 58

7
[ 1313738-80-5 ]
5-chloro-3-methyl-2-(piperidin-3-yl)pyridine [ No CAS ]

Reference： [1]Patent: WO2015/79224,2015,A1

8
[ 1313738-80-5 ]
2-(1-benzylpiperidin-3-yl)-5-chloro-3-methylpyridine [ No CAS ]

Reference： [1]Patent: WO2015/79224,2015,A1

9
N-benzyl-1,2,3,6-tetrahydropyridine-5-carboxylic acid [ No CAS ]
[ 1313738-80-5 ]

Reference： [1]Patent: CN105503924,2016,A

10
5-iodo-N-benzyl-1,2,3,6-tetrahydropyridine [ No CAS ]
[ 73183-34-3 ]
[ 1313738-80-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80.0℃;Inert atmosphere;	Under nitrogen protection,In the three reaction bottles to join90mLDMSO, Iodine (15.8 g), 0.39 g (0.53 mmol) of PdCl2dppf, 14.5 g (0.15 mol) of anhydrous potassium acetate,And boronic acid pinacol ester 13.4 g (53 mmol) were addedGradually slow warming to completeThe mixture was stirred at 80 C overnight. The reaction was complete by GC (product / raw material> 100: 1). After filtration, the filtrate was evaporated to dryness. Ethyl acetate and activated charcoal were added and the mixture was refluxed for 1 hour. After adding ethanol and n-heptane, the reaction was cooled to -10 C and stirred to obtain 12.4 g of N-benzyl-1,2,3,6-tetrahydropyridine-5-boronic acid pinacol ester as a white solid product, Yield 78%.

Reference： [1]Patent: CN105503924,2016,A .Location in patent: Paragraph 0022

11
[ 1313738-80-5 ]
6-bromo-8-fluoro-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one [ No CAS ]
6-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-8-fluoro-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 60.0℃; for 3.0h;Inert atmosphere;	A suspension of Intermediate 137 (1.5 g, 4.07 mmol) in 1,4-dioxane (15 mL) was treated with l-benzyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2,3,6-tetrahydro- pyridine (1.34 g, 4.48 mmol) and 2M aqueous Na2C03 solution (6.1 mL, 12.2 mmol). The mixture was degassed with N2 for 5 minutes, then Pd(dppf)Cl2'DCM (333 mg, 0.41 mmol) was added. The mixture was heated at 60C for 3 h, then cooled and partitioned between EtOAc (50 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (2 x 30 mL) and the combined organic layers were washed with brine (40 mL), then dried (MgS04). The solvent was removed in vacuo. The residue was purified by column chromatography (Si02; 0-10% MeOH/EtOAc) to afford the title compound (983 mg, 51%). deltaEta (500 MHz, CDC13) 7.46-7.27 (m, 5H), 6.74 (dd, J 11.3, 1.6 Hz, 1H), 6.62 (s, 1H), 5.96 (s, 1H), 4.96 (s, 2H), 4.67 (s, 2H), 3.69 (s, 2H), 3.64 (s, 3H), 3.21 (s, 2H), 2.60 (s, 2H), 2.32 (s, 2H), 2.15 (s, 3H), 2.12 (s, 3H). Method B HPLC-MS: MH+ mlz 461 , RT 1.52 minutes (98%)

Reference： [1]Patent: WO2016/198400,2016,A1 .Location in patent: Page/Page column 172; 173

12
[ 1313738-80-5 ]
(2R)-6-bromo-2-methyl-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-2H,3H,4H-pyrido[3,2-b][1,4]oxazin-3-one [ No CAS ]
(2R)-6-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-2-methyl-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-2H,3H,4H-pyrido[3,2-b][1,4]oxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 60.0℃; for 1.0h;Inert atmosphere;	A solution of Intermediate 132 (300 mg, 0.82 mmol), l-benzyl-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2,3,6-tetrahydropyridine (245.78 mg, 0.82 mmol) and 2M aqueous Na2C03 solution (1.23 mL) in 1,4-dioxane (10 mL) was degassed with N2 for 10 minutes, then Pd(dppf)Cl2 (67.08 mg, 0.08 mmol) was added. The mixture was heated at 60C for 1 h, then cooled to r.t. and partitioned between EtOAc (50 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (2 x 25 mL), then the combined organic layers were dried (Na2S04) and the solvent was removed in vacuo. The residue was purified by column chromatography (Si02; 0-10% MeOH/EtOAc) to give the title compound (300 mg, 80%). deltaEta (500 MHz, CDC13) 7.39 (s, 2H), 7.31 (t, J 7.4 Hz, 2H), 7.26 (s, IH, includes chloroform peak), 7.16 (d, J 8.2 Hz, IH), 6.97 (d, J 8.2 Hz, IH), 6.58 (d, J 3.9 Hz, IH), 5.11 (q, J 14.5 Hz, 2H), 4.59 (q, J 6.8 Hz, IH), 3.72 (s, 2H), 3.65 (s, 3H), 3.48 (s, 2H), 2.64 (s, 2H), 2.36 (d, J 37.3 Hz, 2H), 2.19 (s, 3H), 2.08 (s, 3H), 1.57 (d, J 12.3 Hz, 2H), 1.52 (d, J 6.8 Hz, 3H). Method B HPLC-MS: MH+ mlz 458, RT 1.38 minutes (99%)

Reference： [1]Patent: WO2016/198400,2016,A1 .Location in patent: Page/Page column 170; 171

13
[ 1313738-80-5 ]
(2R)-2-methyl-6-(piperidin-3-yl)-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-2H,3H,4H-pyrido[3,2-b][1,4]oxazin-3-one [ No CAS ]