[ CAS No. 39774-25-9 ] {[proInfo.proName]}

Name: 39774-25-9|2-Amino-6-phenylpyridine|98%
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Quality Control of [ 39774-25-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 39774-25-9 ]

Product Details of [ 39774-25-9 ]

CAS No. :	39774-25-9	MDL No. :	MFCD00234719
Formula :	C₁₁H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDWUSBKLDNVDDQ-UHFFFAOYSA-N
M.W :	170.21	Pubchem ID :	598430
Synonyms :

Calculated chemistry of [ 39774-25-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.08
TPSA :	38.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	2.17
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	1.88
Log Po/w (SILICOS-IT) :	2.31
Consensus Log Po/w :	2.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.88
Solubility :	0.225 mg/ml ; 0.00132 mol/l
Class :	Soluble
Log S (Ali) :	-2.62
Solubility :	0.408 mg/ml ; 0.0024 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.18
Solubility :	0.0113 mg/ml ; 0.0000665 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 39774-25-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 39774-25-9 ]

* 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.

Upstream synthesis route of [ 39774-25-9 ]
Downstream synthetic route of [ 39774-25-9 ]

[ 39774-25-9 ] Synthesis Path-Upstream 1~4

1
[ 1008-89-5 ]
[ 39774-25-9 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 6, p. 1641 - 1649
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 1, p. 96 - 101
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6807 - 6819
[4] Journal of the American Chemical Society, 1956, vol. 78, p. 5842

2
[ 45644-21-1 ]
[ 98-80-6 ]
[ 39774-25-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate In 1,4-dioxane at 100℃; for 5 h; Inert atmosphere; Sealed tube	General procedure: To a solution of the requisite chloro-amino-substituted heteroaromatic in anhydrous 1,4-dioxane (30 volumes wrt chloride) in a sealed tube was introduced phenylboronic acid (1.5 equiv) and finely ground potassium phosphate (2.0 equiv). The solution was degassed (N₂ bubbling) for 5 min, Pd(OAc)₂ (5 mol percent wrt chloride) and di-tert-butylphosphinoferrocene (5 mol percent wrt chloride) introduced and degassing continued for a further 5 min. The tube was sealed under nitrogen and heated with rapid stirring at 100 °C for 5 h. After cooling, the reaction mixture was filtered in vacuo through a celite pad and the precipitated material washed with 1,4-dioxane. The combined filtrates were evaporated and purified by flash column chromatography (neat hexane to 1:1 hexane/EtOAc gradient containing 2.5percent by volume Et₃N) to furnish the biarylanilines 13, 14 and 15.

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2742 - 2750
[2] Tetrahedron Letters, 2005, vol. 46, # 20, p. 3573 - 3577
[3] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432

3
[ 19798-81-3 ]
[ 98-80-6 ]
[ 39774-25-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8781 - 8800
[2] Synthesis, 2010, # 18, p. 3163 - 3173
[3] Patent: WO2006/67931, 2006, A1, . Location in patent: Page/Page column 54-55
[4] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8520 - 8529
[5] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432

4
[ 39774-25-9 ]
[ 39774-26-0 ]

Reference： [1] Patent: WO2006/67931, 2006, A1, . Location in patent: Page/Page column 55
[2] Journal of the American Chemical Society, 1956, vol. 78, p. 5842

[ 39774-25-9 ] Synthesis Path-Downstream 1~58

1
[ 1008-89-5 ]
[ 39774-25-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1641 - 1649
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 96 - 101
[3]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6807 - 6819
[4]Journal of the American Chemical Society,1956,vol. 78,p. 5842

2
[ 39774-25-9 ]
[ 39774-26-0 ]

Reference： [1]Patent: WO2006/67931,2006,A1 .Location in patent: Page/Page column 55
[2]Journal of the American Chemical Society,1956,vol. 78,p. 5842

3
[ 39774-25-9 ]
[ 1484-88-4 ]
2,4,6,6'-Tetraphenyl-[1,2']bipyridinyl-1-ylium; perchlorate [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 126 - 138

4
[ 39774-25-9 ]
2-imino-6-cyclohexylpiperidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 96 - 101

5
[ 39774-25-9 ]
2,6-diphenyl-4-tert-butylpyrilium perchlorate [ No CAS ]
1-(6-Phenylpyridin-2-yl)-4-tert-butyl-2,6-diphenylpyridinium perchlorate [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1999,vol. 64,p. 1274 - 1294

Yield	Reaction Conditions	Operation in experiment
95%Spectr.	With palladium diacetate; In water; at 100℃; for 4h;Inert atmosphere;	General procedure: A mixture of A -X (as provided in Table 3, 10 mmol, 1.0 equiv), phenylboronic acid (as provided in Table 3), Pd(OAc)2 (0.4 mmol, 0.04 equiv) and H20 (25 mL, 1384 mmol) in a 3 -neck round-bottom flask was stirred under reflux at 100 C in a N2 atmosphere for the time listed in Table 1. The initial and final pH values of the aqueous phase were measured before and after the heating was enabled when the temperature was stabilized at 25 - 27 C, and listed in Table 3. The initial reaction time (t = 0) was taken when the reaction mixture reached an internal temperature of 100 C; the time to reach this temperature was approximately 20 - 30 minutes. The reactions were biphasic with an aqueous phase and a solid phase. The cooled reaction mixture was basified to pH > 12 using 30% NaOH aqueous solution, and then was thoroughly extracted with ethyl acetate. The combined organic phase is dried over anhydrous MgSC , filtered, and then concentrated in vacuo. The crude product was analyzed by GC and 1H NMR, as provided in Table 3.

7
[ 39774-25-9 ]
[ 100-07-2 ]
4-methoxy-<i>N</i>-(6-phenyl-pyridin-2-yl)-benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 749 - 762

8
[ 45644-21-1 ]
[ 98-80-6 ]
[ 39774-25-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In 1,4-dioxane; at 100℃; for 5h;Inert atmosphere; Sealed tube;	General procedure: To a solution of the requisite chloro-amino-substituted heteroaromatic in anhydrous 1,4-dioxane (30 volumes wrt chloride) in a sealed tube was introduced phenylboronic acid (1.5 equiv) and finely ground potassium phosphate (2.0 equiv). The solution was degassed (N2 bubbling) for 5 min, Pd(OAc)2 (5 mol % wrt chloride) and di-tert-butylphosphinoferrocene (5 mol % wrt chloride) introduced and degassing continued for a further 5 min. The tube was sealed under nitrogen and heated with rapid stirring at 100 C for 5 h. After cooling, the reaction mixture was filtered in vacuo through a celite pad and the precipitated material washed with 1,4-dioxane. The combined filtrates were evaporated and purified by flash column chromatography (neat hexane to 1:1 hexane/EtOAc gradient containing 2.5% by volume Et3N) to furnish the biarylanilines 13, 14 and 15.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2742 - 2750
[2]Tetrahedron Letters,2005,vol. 46,p. 3573 - 3577
[3]New Journal of Chemistry,2017,vol. 41,p. 15420 - 15432

9
[ 39774-25-9 ]
[ 3196-23-4 ]
[ 911717-60-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6807 - 6819

10
[ 39774-25-9 ]
1-(6-phenyl-pyridin-2-ylamino)-cyclohexanecarboxylic acid [2-(4-methoxy-phenylamino)-ethyl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6807 - 6819

11
[ 39774-25-9 ]
[ 39065-47-9 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5842

12
[ 39774-25-9 ]
[ 59576-29-3 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5842

13
[ 39774-25-9 ]
[ 107771-78-8 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5842

14
[ 19798-81-3 ]
[ 98-80-6 ]
[ 39774-25-9 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 8781 - 8800
[2]Synthesis,2010,p. 3163 - 3173
[3]Journal of Medicinal Chemistry,2019
[4]Patent: WO2006/67931,2006,A1 .Location in patent: Page/Page column 54-55
[5]Journal of Organic Chemistry,2016,vol. 81,p. 8520 - 8529
[6]New Journal of Chemistry,2017,vol. 41,p. 15420 - 15432

15
[ 39774-25-9 ]
[ 169759-60-8 ]
[ 169760-12-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 5,5-dimethyl-1,3-cyclohexadiene; diethyl ether;	EXAMPLE 20 6-(2Furyl)-4-hydroxy-2-methyl-N-[6-phenyl-2-pyridinyl]-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide 500 mg (1.46 mmol) of methyl 6-(2-furyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylate 1,1-dioxide and 431 mg (1.46 mmol) of 6-phenyl-2-pyridinamine are heated to boiling in 6 ml of absolute xylene for 4 hours. After the reaction mixture has cooled, the precipitate is filtered off and digested twice with 15 ml of cold diethyl ether each time. The crude product is recrystallized from toluene/active charcoal. Yield: 360 mg of yellow crystals (51% of theory) TLC: solvent PE: EtOH=2:1; 0.3 M.p.: 210-213 C. (toluene) 1 H-NMR: (DMSO-d6) d(ppm): 8.15-8.05 (m, 2H, Bz-H2,6); 8.04-7.82 (m, 4H, Thaz-H7, Fu-H5, Py-H3,4); 7.78 (d, 1H, Py-H5); 7.57-7.44 (m, 3H, Bz-H3,4,5); 7.22 (d, 1H, Fu-H3); 6.69 (dd, 1H, Fu-H4) 13 C-NMR: (DMSO-d6) d(ppm): 166.4; 156.5; 153.7; 150.2; 146.8; 144.6; 140.1; 139.3; 138.9; 136.9; 133.2; 129.6; 128.8; 126.7; 117.8; 116.6; 114.5; 112.9; 110.0; 109.8; 39.6

Reference： [1]Patent: US5679678,1997,A

16
[ 39774-25-9 ]
[ 157198-80-6 ]
2-Benzimidazol-1-yl-N-(6-phenyl-pyridin-2-yl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In N,N-dimethyl-formamide; at 20℃; for 17h;	EXAMPLE 2 2-Benzimidazol-1-yl-N-(6-phenyl-pyridin-2-yl)-acetamide To a solution of (1H-benzimidazol-1-yl)acetic acid (1 g, 5.68 mmol) (Example 1B) in N,N-dimethylformamide (25 mL) was added thionyl chloride (0.4 mL, 5.56 mmol) drop-wise and the reaction mixture stirred at room temperature for 1 h. 6-Phenyl-pyridin-2-ylamine (5.46 mmol) and pyridine (4 mL) were then added to the reaction mixture and stirred at room temperature for 17 h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluding with 0-10% methanol in dichloromethane, affording the title compound. 1H NMR (400 MHz, CD3OD) delta ppm 5.29 (2H, s), 7.28-7.35 (2H, m), 7.39-7.48 (3H, m), 7.54 (1H, d, J=7.2 Hz), 7.62 (1H, d, J=7.7 Hz), 7.71 (1H, d, J=7.3 Hz), 7.81 (1H, t, J=7.9 Hz), 7.98 (1H, br d), 8.05 (2H, d, J=7.3 Hz), 8.23 (1H, s). MS (ES) m/z: 329.1 [M+H].

Reference： [1]Patent: US2007/112034,2007,A1 .Location in patent: Page/Page column 5

17
[ 39774-25-9 ]
[ 15243-33-1 ]
[ 75-09-2 ]
[Ru6(μ3-H)(μ5-η3-apyC6H4-N,N,C)(μ-CO)3(CO)13] [ No CAS ]
[Ru6(μ3-H)2(μ5-η2-apyPh-N,N)(μ-CO)2(CO)14]*(CH2Cl2)0.5 [ No CAS ]