[ CAS No. 1924-77-2 ] {[proInfo.proName]}

Name: 1924-77-2|[1,1'-Biphenyl]-2-ylmethanamine|95%
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3d Animation Molecule Structure of 1924-77-2

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Quality Control of [ 1924-77-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1924-77-2 ]

SDS Specification

Alternatived Products of [ 1924-77-2 ]

Product Details of [ 1924-77-2 ]

CAS No. :	1924-77-2	MDL No. :	MFCD00270123
Formula :	C₁₃H₁₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YHXKXVFQHWJYOD-UHFFFAOYSA-N
M.W :	183.25	Pubchem ID :	263366
Synonyms :

Calculated chemistry of [ 1924-77-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.55
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	2.41
Log Po/w (WLOGP) :	2.66
Log Po/w (MLOGP) :	3.08
Log Po/w (SILICOS-IT) :	3.18
Consensus Log Po/w :	2.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.185 mg/ml ; 0.00101 mol/l
Class :	Soluble
Log S (Ali) :	-2.6
Solubility :	0.462 mg/ml ; 0.00252 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.96
Solubility :	0.00201 mg/ml ; 0.000011 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.44

Safety of [ 1924-77-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1924-77-2 ]

* 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 [ 1924-77-2 ]
Downstream synthetic route of [ 1924-77-2 ]

[ 1924-77-2 ] Synthesis Path-Upstream 1~1

1
[ 1924-77-2 ]
[ 19853-10-2 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 275

[ 1924-77-2 ] Synthesis Path-Downstream 1~88

1
[ 24973-49-7 ]
[ 1924-77-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With aluminum (III) chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere;	General procedure: A stirring suspension of lithium aluminum hydride (1.1equiv) in anhydrous THF was treated dropwise under N2 with a solution of aluminum chloride (0.9equiv) in THF. The reaction mixture was maintained at room temperature during the addition by means of a water bath. After addition was complete, the reaction mixture was stirred vigorously for 20min and then cooled to 0C before adding dropwise a solution of biphenyl-2-carbonitrile 4 (1.0equiv) in THF. After complete addition, stirring was continued for 2h and the reaction was quenched by slowly adding methanol followed by water. The mixture was concentrated under reduced pressure, and the residue was extracted with 1N HCl. The aqueous phase were combined, washed with EtOAc and neutralized by addition of 10N NaOH. The mixture was extracted with CH2Cl2, the organic phase was combined, washed with water, dried over Na2SO4 and evaporated under reduced pressure. The residue was filtered through a pad of silica gel, and the filtrate was evaporated and dried to give the product 5 in 60-75% yields. 4.3.1 Biphenyl-2-ylmethanamine (5-1) The reaction of lithium aluminum hydride (2.15 ml, 2.15 mmol) in anhydrous THF, aluminum chloride (234 mg, 1.76 mmol), and biphenyl-2-carbonitrile (350 mg, 1.95 mmol) in THF (5 ml) gave the title compound 5-1 (256 mg, 1.40 mmol, 72% yield). 1H NMR (400 MHz, CDCl3) delta 7.46 (d, J = 7.5 Hz, 1H), 7.41-7.40 (m, 2H), 7.37-7.32 (m, 3H), 7.30 (td, J = 7.5, 1.3 Hz, 1H), 7.24 (dd, J = 8.1, 2.1 Hz, 1H), 3.81 (s, 2H), 1.34 (s, 2H).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596
[2]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275
[3]Journal of the American Chemical Society,1940,vol. 62,p. 514

2
[ 1924-77-2 ]
[ 2928-43-0 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506
[2]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

3
[ 64-18-6 ]
[ 1924-77-2 ]
[ 140670-04-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 627 - 632

4
[ 1924-77-2 ]
[ 79-04-9 ]
N-(chloroacetyl)-2-phenylbenzylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 184 - 193

5
[ 1924-78-3 ]
[ 1924-77-2 ]

Reference： [1]Journal of the Chemical Society,1965,p. 1252 - 1257

6
{1-[<i>N</i>'-(imidazole-1-carbonyl)-hydrazinocarbonyl]-propyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
[ 1924-77-2 ]
C₂₃H₃₀N₄O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4408 - 4424

7
[ 98027-74-8 ]
[ 1924-77-2 ]
biphenyl-2-ylmethyl-(5-nitro-4-thiocyanato-pyrimidin-2-yl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 225 - 230

8
[ 914646-71-2 ]
[ 1924-77-2 ]
[ 914646-89-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7625 - 7651

9
[ 914647-55-5 ]
[ 1924-77-2 ]
[ 914647-58-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7625 - 7651

10
[ 1924-77-2 ]
[ 391680-92-5 ]
5,6-dihydroxy-2-thiophen-2-yl-pyrimidine-4-carboxylic acid (biphenyl-2-ylmethyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 350 - 353

11
[ 590-93-2 ]
[ 119072-55-8 ]
[ 1924-77-2 ]
[ 1002557-15-4 ]

Yield	Reaction Conditions	Operation in experiment
		(biphenyl-2-ylmethyl)amine (23.78 mmol, 4.36 g) was dissolved in MeOH and 2-furaldehyde (23.78 mmol, 2.29 g) and but-2-ynoic acid (23.78 mmol, 2.00 g) was added. The mixture was stirred at rt for 30 min. Tert-butyl isocyanide (23.78 mmol, 1.98 g) was added and the mixture was stirred at rt over night. The solvent was removed by evaporation. The product was taken on to the next step without further purification.

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 38

12
[ 1924-77-2 ]
4-(isocyanomethyl)benzonitrile [ No CAS ]
2-(biphenyl-2-ylmethyl)-N-(4-cyanobenzyl)-3-oxoisoindoline-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.8%		2-formylbenzoic acid (9.09 mmol, 1.36 g) was dissolved in Methanol (20 ml) and 1-<strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (9.09 mmol, 1.66 g) was added and the mixture was stirred at rt for 30 minutes. Then 4-(isocyanomethyl)benzonitrile (9.09 mmol, 1.29 g) dissolved in Acetonitrile (5 ml) was added to the mixture. The reaction was stirred at rt over night. The crude was purified by flashcromatography (started with isocratic Toluene/EtOAc 100/0 and then the EtOAc concentration was increased to 50%, (silica gel 60 0.004-0.063 mm). The product containing fractions was pooled and the solvent was removed by evaporation to give the title compound (2.32 g, 55.8%). 1H-NMR (500 MHz, CDCl3): delta 7.63-7.56 (m, 3H), 7.50-7.45 (m, 2H); 7.45-7.39 (m, 3H); 7.37-7.24 (m, 4H); 7.22-7.16 (m, 3H); 7.00 (d, 2H); 6.59-6.54 (m, 1H); 5.24 (d, 1H), 4.77 (s, 1H); 4.31 (d, 1H); 4.29-4.18 (m, 2H).

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 39

13
[ 319457-34-6 ]
[ 1924-77-2 ]
C₂₃H₁₈F₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 50℃;	2-acetyl-3,6-difluorobenzoic acid (0.24 mmol, 50 mg) was dissolved in Methanol (1 ml) and (biphenyl-2-ylmethyl)amine (0.24 mmol, 46 mg) was added. The mixture was stirred at 50 C. over night to form the imine. Then tert-butyl isocyanide (0.24 mmol, 21 mg) dissolved in Acetonitrile was added to mixture. The reaction was stirred at 50 C. for 170 h. The product precipitated and was filtered of and the solid was washed with EtOAc to give the title compound (23 mg, 20.5%). 1H-NMR (500 MHz, CDCl3): delta 7.64-7.56 (m, 1H), 7.52-7.43 (m, 2H), 7.42-7.08 (m, 8H), 5.08 (s, 1H), 4.65 (dd, 2H), 1.37 (s, 3H), 0.94 (s, 9H); HRMS calculated for (C27H26F2N2O2+H)+, 449.5250; found (ES [M+H]+), 449.5248

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 41

14
[ 119072-55-8 ]
[ 1924-77-2 ]
2-(biphenyl-2-ylmethyl)-6-bromo-N-(tert-butyl)-3-oxoisoindoline-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.4%		1-<strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (0.225 g, 1.23 mmol) and 5-bromo-3-hydroxy-2-benzofuran-1(3H)-one (Preparation W) (0.283 g, 1.24 mmol) was added to a flask, MeOH (1 mL) was added an the mixture was left stirring in r.t. for 3 h. tert-butyl isocyanide (0.139 mL, 1.23 mmol) was added to the mixture and the reaction was left stirring in r.t. over night. The solvent was evaporated, the crude was dissolved in DCM (4 mL) and extracted with water (3 mL), the organic phase was collected and the solvent was evaporated. The crude was purified by flash chromatography (SP1 flash system from Biotage, silica cartridge), using heptane and EtOAc as eluent, followed by concentration in vacuo afforded the title compound (0.191 g, 32.4%). 13C-NMR (500 MHz, CDCl3) delta 168.58, 166.16, 143.65, 142.49, 140.52, 133.37, 132.34, 130.62, 130.46, 129.15, 128.62, 128.35, 128.15, 127.99, 127.87, 127.28, 126.31, 125.21, 124.92, 62.87, 51.61, 42.93, 31.88, 28.99, 27.52, 27.24, 22.58, 13.28; HRMS calculated for (C26H25BrN2O2+H)+, 477.1178 found (ES [M+H]+), 477.1173

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 44

15
[ 1002556-88-8 ]
[ 1924-77-2 ]
2-(biphenyl-2-ylmethyl)-N-(4,4-difluorobutyl)-3-oxoisoindoline-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		The 1-<strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (0.400 mmol) was dissolved in MeCN (1 mL) and added to 2-Formylbenzoic acid (0.400 mmol) dissolved in MeOH (1 mL), this was stirring for 30 min in r.t 1,1-difluoro-4-isocyanobutane (preparation P) (0.400 mmol) dissolved in MeCN (2 mL) was added to the mixture and the reaction was left stirring in r.t. over night. The reaction was finished the next morning and the solvent was evaporated. The crude was dissolved in DCM (4 mL) and extracted with water (3 mL), the organic phase was collected and the solvent was evaporated. The crude was dissolved in DMSO (1 ml), filtrated and purified by preparative HPLC using a Waters FractionLynx I HPLC system with a mass triggered fraction collector, equipped with an Xbridge Prep C18 15019 mm column using a MeCN/0.2% NH3 buffer system with a gradient from 100% A (5% MeCN+95% 0.2% NH3) to 100% B (95% MeCN+5% 0.2% NH3) as mobile phase, followed by concentration in vacuo afforded the title compound (0.057 g, 33%). 1H-NMR (600 MHz, DMSO-d6, DMSO*) delta 8.526-8.3 (m, 1H), 7.75-7.03 (m, 13H), 6.2-5.85 (m, 1H), 5.27-5.07 (d, 1H), 4.83-4.66 (s, 1H), 4.13-3.85 (d, 1H), 3.1-2.83 (m), 1.81-1.55 (m, 2H), 1.5-1.27 (m, 2H); HRMS calculated for (C26H24F N2O2+H)+, 435.1884 found (ES [M+H]+), 435.1865

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 44

16
[ 119072-55-8 ]
[ 1924-77-2 ]
2-(biphenyl-2-ylmethyl)-N-tert-butyl-3-oxoisoindoline-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 2-formylbenzoic acid (2.50 g, 16.7 mmol) and 1-<strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (3.05 g, 16.7 mmol) in MeOH (55 ml) was stirred at room temperature for 1 h and then tert-butyl isocyanide (1.38 g, 16.7 mmol) was added. The resulting mixture was stirred at room temperature over night and concentrated under reduced pressure. Crystals were obtained by adding ethanol to the residue. The crystals (2.06 g) were filtered off and dried in vacuo. The filtrate was purified by flash chromatography (SP1 flash system from Biotage, silica cartridge), using ethyl acetate (gradient from 6 to 50%) in heptane as eluent. Removal of the solvent gave 2.05 g of a white solid. The products from crystallisation and chromatography were combined and triturated with methanol giving 2.88 g of a white solid. The remaining material was purified by preparative HPLC giving a second crop of 0.70 g. 1H NMR (500 MHz, CD3OD) delta 7.71 (dm, 1H), 7.56 (m, 1H), 7.50 (m, 1H), 7.42 (dm, 1H), 7.38-7.24 (m, 9H), 5.37 (d, 1H), 4.71 (s, 1H), 4.15 (d, 1H), 1.22 (s, 9H); HRMS calculated for (C26H26N2O2+H)+, 399.2066; found (ESI [M+H]+), 399.2073.

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 44-45

17
[ 1924-77-2 ]
1-(2S-2-aminobutanoyl)-4-([1,1'-biphenyl-2-yl]methyl)semicarbazide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4408 - 4424

18
[ 1924-77-2 ]
N-<(N',N'-diethylamino)acetyl>-2-phenylbenzylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 184 - 193

19
[ 1924-77-2 ]
[ 38580-83-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

20
[ 1924-77-2 ]
[ 19853-10-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

21
[ 1924-77-2 ]
[ 14676-52-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

22
[ 1924-77-2 ]
1-(2-phenyl-benzyl)-piperidine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506

23
[ 1924-77-2 ]
[ 643-58-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

24
[ 1924-77-2 ]
[ 19853-09-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275
[2]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506

25
[ 1924-77-2 ]
4-([1,1'-biphenyl]-2-ylmethyl)morpholine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506

26
[ 1924-77-2 ]
[ 96003-60-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

27
[ 1924-77-2 ]
[ 19853-17-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

28
[ 1924-77-2 ]
[ 19853-18-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

29
[ 1924-77-2 ]
[ 78383-16-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

30
[ 1924-77-2 ]
[ 860589-80-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

31
[ 1924-77-2 ]
[ 857829-51-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1929,vol. 468,p. 275

32
[ 1924-77-2 ]
(2-phenyl-benzyl)-dipropyl-amine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506

33
[ 1924-77-2 ]
diisopropyl-(2-phenyl-benzyl)-amine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506

34
[ 1924-77-2 ]
dibutyl-(2-phenyl-benzyl)-amine [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 489,506

35
N-(4-carbamimidoyl-phenyl)-2-phenyl-malonamic acid sodium salt [ No CAS ]
[ 1924-77-2 ]
CH₂O₂*C₂₉H₂₆N₄O₂ [ No CAS ]

Reference： [1]Patent: EP1193248,2002,A1 .Location in patent: Page 22

36
[ 93-58-3 ]
N-Chlorocarbamoyl-4-[(4-cyclohexylphenylamino)methyl]benzoic acid methyl ester [ No CAS ]
[ 1924-77-2 ]
[ 385836-47-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 36 3-{4-[3-Biphenyl-2-ylmethyl-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2(R)-hydroxypropionic acid This compound was prepared similarly as described in example 35 from N-chlorocarbamoyl-4-[(4-cyclohexylphenylamino)methyl]benzoic acid methyl ester and biphenyl-2-ylmethylamine followed by hydrolysis of the benzoic acid methyl ester, coupling with (R)-isoserine ethyl ester hydrochloride. Hydrolysis afforded the title compound. 1H-NMR (DMSO-d6): delta12.6 (s, 1H), 8.45 (t, 1H), 7.78 (d, 2H), 7.45-7.20 (m, 14H), 7.05 (d, 2H), 6.10 (t, 1H), 5.50 (bs, 1H), 4.85 (s, 2H), 4.2 (m, 3H), 3.55 (m, 1H), 2.45 (m, 1H), 1.85-1.70 (m, 5H), 1.40-1.20 (m, 6H); HPLC-MS (method B): m/z=606 (M+1); Rt=5.08 min.

Reference： [1]Patent: US2002/143186,2002,A1

37
[ 1924-77-2 ]
[ 257939-97-2 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Part C. Preparation of 2-ethyl-1,5,6,7-tetrahydro-1-(2-phenyl-phenylmethyl)-4H-indol-4-one 2-Phenyl-phenylmethyl amine (3 g, 0.0164 mol) and an equivalent amount of 2-(2-oxobutyl)-1,3-Cyclohexyldione were dissolved in 30 mL of toluene and heated at reflux temperature with a water separator. After several hours, solvent was stripped off and the residue subjected to flash chromatography on silica eluding with 3:1 hexane/ethyl acetate to afford 4.5 g of the subtitled compound as an oil.

Reference： [1]Patent: US6451839,2002,B1

38
[ 1924-77-2 ]
2'-(benzyloxycarbonylaminomethyl)biphenyl-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water;	General procedure for the reaction of aminomethylbiphenyls with isothiocyanates to give thioureas (Examples 9a-9i): 0.36 mmol of the respective isothiocyanate dissolved in 0.5 ml of methylene chloride is slowly added dropwise at 0 C. to a solution of 0.34 mmol of the respective 2'-aminomethylbiphenyl and 41 mg (0.41 mmol) of triethylamine in 5 ml of methylene chloride. After stirring at RT for 3 h, the reaction mixture is concentrated in vacuo, the residue is stirred with 25 ml of water and the precipitated product is filtered off with suction or purified by preparative HPLC.

Reference： [1]Patent: US6531495,2003,B1

39
[ 187884-94-2 ]
[ 1924-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hydrazine hydrate;	Part B. Preparation of 2-phenyl-phenylmethyl amine N-(2-Phenyl-phenylmethyl)-phthalimide (6.5 g) in 25 cc of hydrazine hydrate were stirred at room temperature overnight. Ice water was added and the solid separated by filtration. The filtrate was salted out with brine and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate, filtered and concentrated to dryness to afford 3 g of subtitled product as an oil.

Reference： [1]Patent: US6451839,2002,B1

40
[ 1924-77-2 ]
[ 60444-20-4 ]
[ 1219808-13-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In benzene; at 20 - 65℃; for 18h;	1-(biphenyl-2-ylmethyl)-2-ethyl-1 H-pyrrole, 13 : To the crude 12 (14 g, 83 mmol) in dry benzene (200 mL) at room temperature is added <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> solution (100 mmol) and triethylamine (110mmol). The solution is heated to reach 65 C and stirred for 18 h. The resulted reaction mixture is filtered and concentrated. The crude product was purified by silica gel chromatography to afford 13
	With triethylamine; In benzene; at 20 - 65℃; for 18h;	13 : To the crude 12 (14 g, 83 mmol) in dry benzene (200 ml_) at room temperature is added <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> solution (100 mmol) and triethylamine (110mmol). The solution is heated to reach 65 0C and stirred for 18 h. The resulted reaction mixture is filtered and concentrated. The crude product was purified by silica gel chromatography to afford 13
	With triethylamine; In benzene; at 20 - 65℃; for 18h;	To the crude 12 (14 g, 83 mmol) in dry benzene (200 mL) at room temperature is added <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> solution (100 mmol) and triethylamine (110 mmol). The solution is heated to reach 65 C. and stirred for 18 h. The resulted reaction mixture is filtered and concentrated. The crude product was purified by silica gel chromatography to afford 13

Reference： [1]Patent: WO2007/56184,2007,A2 .Location in patent: Page/Page column 98; 99
[2]Patent: WO2007/56279,2007,A2 .Location in patent: Page/Page column 243-244
[3]Patent: US2007/135385,2007,A1 .Location in patent: Page/Page column 132-133

41
(3S*,5R*)-5-(toluene-4-sulfonylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester [ No CAS ]
[ 1924-77-2 ]
C₃₁H₃₇N₃O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A small part of the residue obtained below under A. (40 mg, 0.1 mmol) is dissolved in pyridine (0.5 mL). The solution is cooled to 2 C., treated with O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate and stirred at 2 C. for 1 h. The resulting mixture is added to a precooled solution of <strong>[1924-77-2]2-phenylbenzylamine</strong> (18.3 mg, 0.1 mmol) in pyridine (0.4 mL). The reaction mixture is stirred at 4 C. for 14 h, evaporated in an air stream and the residue evaporated twice with CH2Cl2. The crude product is dissolved in CH2Cl2 (2 mL) and put on a 3 mL HM-N cartridge (isolute) pretreated with an aqueous 10% K2CO3 solution (2 mL). The compound is eluted with CH2Cl2 (2×6 mL). The organic layer is evaporated and dried at RT. A solution of CH2Cl2/trifluoroacetic acid (1:1) is added to the residue, the mixture is shaken for 1 h at RT and evaporated. The residue is purified by preparative HPLC (C18 column, 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 30 ml/min) to afford the title compound. MS: 464.2. [M+H]+; tR (HPLC, C18 column; 5-100% CH3CN+0.05% TFA/H2O+0.05% TFA for 6 min, flow 1.5 ml/min): 3.36 min.

Reference： [1]Patent: US2009/233920,2009,A1 .Location in patent: Page/Page column 46

42
[ 75-44-5 ]
[ 22143-95-9 ]
[ 1924-77-2 ]
biphen-2-ylmethyl-carbamic acid tropenol ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		,67 g (0,02 mol) 2-Phenylbenzylamin werden in 250 ML gesaettigter Natriumbicarbonatloesung und 250 ml Dichlormethan vorgelegt. Bei 0 C werden 52,9 ml (0,10 mol) 20% ige Phosgen-Toluolloesung unter die DICHLORMETHANOBERFLaeCHE zugegeben. Es wird 30 Minuten heftig geruehrt. Die zwei Phasen werden getrennt, die organische Phase ueber Natriumsulfat getrocknet und zur Trockene eingedampft. Der Rueckstand wird in 20 ml Acetonitril geloest und 4,18 g (0,03 mol) Tropenol in 10 ml Acetonitril zugetropft, wobei ein Niederschlag ausfaellt. Es wird 12 Stunden bei Raumtemperatur geruehrt. Der Niederschlag wird abgesaugt und die Mutterlauge zur Trockene eingedampft. Der Rueckstand wird in Dichlormethan geloest und mit Wasser, essigsaurem Wasser (2 Tropfen Eisessig auf 100 ML Wasser) und 10 % iger Natriumcarbonatloesung gewaschen. Die organische Phase wird getrocknet und zur Trockene eingedampft. Ausbeute : 2,85 g (= 41% d. Th.).

Reference： [1]Patent: WO2004/48373,2004,A1 .Location in patent: Page 36

43
[ 75-44-5 ]
[ 22143-95-9 ]
[ 1924-77-2 ]
biphen-2-ylmethyl-carbamic acid tropenol ester methobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		,67 g (0,02 mol) 2-Phenylbenzylamin werden in 250 ML gesaettigter Natriumbicarbonatloesung und 250 ml Dichlormethan vorgelegt. Bei 0 C werden 52,9 ml (0,10 mol) 20% ige Phosgen-Toluolloesung unter die DICHLORMETHANOBERFLaeCHE zugegeben. Es wird 30 Minuten heftig geruehrt. Die zwei Phasen werden getrennt, die organische Phase ueber Natriumsulfat getrocknet und zur Trockene eingedampft. Der Rueckstand wird in 20 ml Acetonitril geloest und 4,18 g (0,03 mol) Tropenol in 10 ml Acetonitril zugetropft, wobei ein Niederschlag ausfaellt. Es wird 12 Stunden bei Raumtemperatur geruehrt. Der Niederschlag wird abgesaugt und die Mutterlauge zur Trockene eingedampft. Der Rueckstand wird in Dichlormethan geloest und mit Wasser, essigsaurem Wasser (2 Tropfen Eisessig auf 100 ML Wasser) und 10 % iger Natriumcarbonatloesung gewaschen. Die organische Phase wird getrocknet und zur Trockene eingedampft. Ausbeute : 2,85 g (= 41% d. Th.).

Reference： [1]Patent: WO2004/48373,2004,A1 .Location in patent: Page 37

44
[ 933-20-0 ]
[ 1924-77-2 ]
[ 1189819-47-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5229 - 5232

45
[ 1924-77-2 ]
[ 4755-77-5 ]
[ 1210914-60-5 ]

Reference： [1]European Journal of Inorganic Chemistry,2009,p. 1989 - 1999

46
[ 1257330-66-7 ]
[ 1924-77-2 ]
[ 96989-50-3 ]
[ 1257330-57-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6213 - 6216

47
[ 139277-58-0 ]
[ 1924-77-2 ]
[ 96989-50-3 ]
[ 1257330-58-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6213 - 6216

48
[ 1924-77-2 ]
[ 96989-50-3 ]
[ 2381-75-1 ]
[ 1257330-47-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6213 - 6216

49
[ 1924-77-2 ]
[ 96989-50-3 ]
2-(isothiocyanatom-ethyl)-1,1’-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 55℃; for 1.5h;Molecular sieve;	To a solution of 0.25 M di-pyridyl-thiocarbonate in DMF (stored on molecular sieves 3A) (1.05 eq) was added 0.1 M amine (free base) 0.1 M in DMF (1eq). The reaction mixture was heated at 55 C for 1.5 h.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 244 - 261

50
[ 1924-77-2 ]
[ 1489288-15-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 244 - 261

51
[ 1924-77-2 ]
tert-butyl ((3-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)methyl)carbamate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5258 - 5261

52
[ 1924-77-2 ]
Umemoto's reagent [ No CAS ]
C₁₄H₁₂F₃N [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5258 - 5261

53
[ 1414571-74-6 ]
[ 1924-77-2 ]
[ 1610415-58-1 ]

Yield	Reaction Conditions	Operation in experiment
34%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h;	Example 50 1 -([1,1 ?-biphenyl]-2-ylmethyl)-3-(1 ?.4-dimethyl- 1 -phenyl- 1 H. 1 ?H-[3 .4?-bipyrazoll-5-yl)urea1008951 To a solution of [1,1?-biphenyl]-2-ylmethanamine (12 mg, 0.065 mmol) in DCM (1 mL) were added phenyl (1?,4-dimethyl-1-phenyl-1H,PH-[3,4?-bipyrazol]-5- yl)carbamate (Intermediate 5, 24.5 mg, 0.065 mmol) then DIEA (0.023 mL, 0.131 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, then purified by reverse- phase column chromatography, eluting with 0-85% acetonitrile/water, to afford the title compound as a white solid (10 mg, 0.022 mmol, 34% yield). MS (apci) mlz = 463.2 (M+H).

Reference： [1]Patent: WO2014/78331,2014,A1 .Location in patent: Paragraph 00895

54
[ 1226772-74-2 ]
[ 1924-77-2 ]
[ 1617539-96-4 ]

Yield	Reaction Conditions	Operation in experiment
9 mg	With potassium phosphate; In N,N-dimethyl acetamide; at 70℃; for 14h;	1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester To a stirred solution of 3-dimethylamino-2-(3-fluoro-pyridine-2-carbonyl)acrylic acid ethyl ester (4) (18 mg, 0.067 mmol) in dimethylacetamide (2 mL) was added K3PO4 (28 mg, 0.14 mmol) followed by <strong>[1924-77-2]C-biphenyl-2-yl-methylamine</strong> (5) (11 mg, 0.06 mmol) at room temperature. The mixture was stirred at 70 C. for 14 h. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified using normal silica gel column chromatography (3% methanol:dichloromethane) to get 1-biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester (6) (9 mg, 35%) as a sticky solid. LC-MS: 385.4 (M+H).

Reference： [1]Patent: US2014/194432,2014,A1 .Location in patent: Paragraph 0127-0129

55
[ 98-80-6 ]
[ 1924-77-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596

56
[ 1924-77-2 ]
[ 732298-45-2 ]
N-(biphenyl-2-ylmethyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		General procedure: HBTU or HATU (1.3equiv) and Et3N (4equiv) were added to a solution of (4-(2-methoxyphenyl)piperazin-1-yl)alkanoic acid 9 (1.1equiv) in acetonitrile at room temperature. The resulting mixture was stirred at room temperature for 30min. A solution of <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (1equiv) in acetonitrile was added to the reaction mixture. The resulting mixture was stirred for additional 6h. After reaction was completed, MeOH was added to the reaction mixture and the resulting solution was evaporated. The residue was purified with by silica gel column chromatography (CH2Cl2/mixture (CH2Cl2/MeOH/H2O/NH3=80:20:1:1)=8/1) to give the desired product 1 in 23-98 % yields. 4.6.1 N-(Biphenyl-2-ylmethyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propanamide (1-1) The reaction of 3-(4-(2-methoxyphenyl)piperazin-1-yl)propanoic acid (80 mg, 0.30 mmol), <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (50 mg, 0.27 mmol), HBTU (133 mg, 0.35 mmol) and Et3N (151 mul, 1.08 mmol) in acetonitrile (3 ml) gave the titled compound 1-1 (60 mg, 0.14 mmol, 52% yield). 1H NMR (400 MHz, CDCl3) delta 8.57 (br s, 1H), 7.46-7.25 (m, 9H), 7.01 (td, J = 7.8, 1.5 Hz, 1H), 6.92 (td, J = 7.6 Hz, 1.5 Hz, 1H), 6.85 (dd, J = 7.8, 1.3 Hz, 1H), 6.82 (dd, J = 7.8, 1.5 Hz, 1H), 4.40 (d, J = 5.2 Hz, 2H), 3.84 (s, 3H), 2.91 (br s, 4H), 2.66-2.63 (m, 6H), 2.40 (t, J = 6.3 Hz, 2H), 1.69 (qd, J = 10.8, 3.6 Hz, 2H); 13C NMR (100 MHz, CDCl3) delta 172.1, 152.3, 141.7, 140.9, 140.7, 135.8, 130.3, 129.1, 128.8 (2C), 128.4, 127.7, 127.4, 127.3, 123.2, 121.0, 118.2, 111.2, 55.4, 53.9, 52.6, 50.5, 41.1, 31.9; LC/MS (ESI+): m/z: calcd for C27H31N3O2: 429.56, [M+H]+; found: 430.55.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596

57
[ 1924-77-2 ]
[ 824958-22-7 ]
N-(biphenyl-2-ylmethyl)-4-(4-(2-methoxyphenyl)piperazin-1-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		General procedure: HBTU or HATU (1.3equiv) and Et3N (4equiv) were added to a solution of (4-(2-methoxyphenyl)piperazin-1-yl)alkanoic acid 9 (1.1equiv) in acetonitrile at room temperature. The resulting mixture was stirred at room temperature for 30min. A solution of <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (1equiv) in acetonitrile was added to the reaction mixture. The resulting mixture was stirred for additional 6h. After reaction was completed, MeOH was added to the reaction mixture and the resulting solution was evaporated. The residue was purified with by silica gel column chromatography (CH2Cl2/mixture (CH2Cl2/MeOH/H2O/NH3=80:20:1:1)=8/1) to give the desired product 1 in 23-98 % yields. 4.6.2 N-(Biphenyl-2-ylmethyl)-4-(4-(2-methoxyphenyl)piperazin-1-yl)butanamide (1-2) The reaction of 4-(4-(2-methoxyphenyl)piperazin-1-yl)butanoic acid (83 mg, 0.30 mmol), <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (50 mg, 0.27 mmol), HBTU (133 mg, 0.35 mmol) and Et3N (151 mul, 1.08 mmol) in acetonitrile (3 ml) gave the titled compound 1-2 (48 mg, 0.11 mmol, 40% yield). 1H NMR (400 MHz, CDCl3) delta 7.41-7.28 (m, 8H), 7.22 (dd, J = 7.3, 1.5 Hz, 1H), 7.05 (m, 1H), 6.91 (t, J = 7.5 Hz, 1H), 6.88-6.86 (m, 2H), 6.65 (br s, 1H), 4.37 (d, J = 5.6 Hz, 2H), 3.85 (s, 3H), 3.13 (br s, 8H), 2.98 (t, J = 5.6 Hz, 2H), 2.48 (t, J = 5.7 Hz, 2H), 1.89 (m, 2H); 13C NMR (100 MHz, CDCl3) delta 174.2, 152.2, 141.7, 140.7, 139.3, 134.7, 130.2, 129.1, 128.6, 128.4, 127.9, 127.6, 124.1, 121., 118.6, 111.5, 58.1, 55.5, 52.9, 48.6, 41.9, 34.5, 20.1; LC/MS (ESI+): m/z: calcd for C28H33N3O2: 443.59, [M+H]+; found: 444.55.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596

58
5-(4-(2-methoxyphenyl)piperazin-1-yl)pentanoic acid [ No CAS ]
[ 1924-77-2 ]
N-(biphenyl-2-ylmethyl)-5-(4-(2-methoxyphenyl)piperazin-1-yl)pentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		General procedure: HBTU or HATU (1.3equiv) and Et3N (4equiv) were added to a solution of (4-(2-methoxyphenyl)piperazin-1-yl)alkanoic acid 9 (1.1equiv) in acetonitrile at room temperature. The resulting mixture was stirred at room temperature for 30min. A solution of <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (1equiv) in acetonitrile was added to the reaction mixture. The resulting mixture was stirred for additional 6h. After reaction was completed, MeOH was added to the reaction mixture and the resulting solution was evaporated. The residue was purified with by silica gel column chromatography (CH2Cl2/mixture (CH2Cl2/MeOH/H2O/NH3=80:20:1:1)=8/1) to give the desired product 1 in 23-98 % yields. 4.6.3 N-(Biphenyl-2-ylmethyl)-5-(4-(2-methoxyphenyl)piperazin-1-yl)pentanamide (1-3) The reaction of 5-(4-(2-methoxyphenyl)piperazin-1-yl)pentanoic acid (88 mg, 0.30 mmol), <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (50 mg, 0.27 mmol), HBTU (133 mg, 0.35 mmol) and Et3N (151 mul, 1.08 mmol) in acetonitrile (3 ml) gave the titled compound 1-3 (90 mg, 0.20 mmol, 73% yield). 1H NMR (400 MHz, CDCl3) delta 7.43-7.23 (m, 9H), 7.03 (td, J = 7.0, 2.0 Hz, 1H), 6.94-6.86 (m, 3H), 5.87 (br s, 1H), 4.41 (d, J = 5.6 Hz, 2H), 3.86 (s, 3H), 3.12 (br s, 4H), 2.81 (br s, 4H), 2.62-2.59 (m, 2H), 2.21-2.18 (m, 2H), 1.63 (m, 4H); 13C NMR (100 MHz, CDCl3) delta 173.0, 152.3, 141.6, 140.7, 130.3, 129.0, 128.6, 128.5, 127.9, 127.5, 127.4, 123.5, 121.0, 118.4, 111.3, 100.0, 57.6, 55.4, 53.3, 49.7, 41.6, 35.5, 28.3, 22.6; LC/MS (ESI+): m/z: calcd for C29H35N3O2: 457.62, [M+H]+; found: 458.55.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596

59
6-(4-(2-methoxyphenyl)piperazin-1-yl)hexanoic acid [ No CAS ]
[ 1924-77-2 ]
N-(Biphenyl-2-ylmethyl)-6-(4-(2-methoxyphenyl)piperazin-1-yl)hexanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		General procedure: HBTU or HATU (1.3equiv) and Et3N (4equiv) were added to a solution of (4-(2-methoxyphenyl)piperazin-1-yl)alkanoic acid 9 (1.1equiv) in acetonitrile at room temperature. The resulting mixture was stirred at room temperature for 30min. A solution of <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (1equiv) in acetonitrile was added to the reaction mixture. The resulting mixture was stirred for additional 6h. After reaction was completed, MeOH was added to the reaction mixture and the resulting solution was evaporated. The residue was purified with by silica gel column chromatography (CH2Cl2/mixture (CH2Cl2/MeOH/H2O/NH3=80:20:1:1)=8/1) to give the desired product 1 in 23-98 % yields. 4.6.4 N-(Biphenyl-2-ylmethyl)-6-(4-(2-methoxyphenyl)piperazin-1-yl)hexanamide (1-4) The reaction of 6-(4-(2-methoxyphenyl)piperazin-1-yl)hexanoic acid (100 mg, 0.33 mmol), <strong>[1924-77-2]biphenyl-2-ylmethanamine</strong> (50 mg, 0.27 mmol), HBTU (133 mg, 0.35 mmol) and Et3N (151 mul, 1.08 mmol) in acetonitrile (3 ml) gave the titled compound 1-4 (45 mg, 0.10 mmol, 35% yield). 1H NMR (300 MHz, CDCl3) delta 7.47-7.26 (m, 9H), 7.06-6.99 (m, 1H), 6.95-6.87 (m, 3H), 5.65 (br t, J = 5.1 Hz, 1H), 4.43 (d, J = 5.4 Hz, 2H), 3.88 (s, 3H), 3.13 (br s, 4H), 2.74 (br s, 4H), 2.50 (t, J = 7.8 Hz, 2H), 2.13 (t, J = 7.5 Hz 2H), 1.52-1.66 (m, 4H), 1.38-1.33 (m, 2H); 13C NMR (75 MHz, CDCl3) delta 172.7, 152.2, 141.6, 141.0, 140.7, 135.5, 130.3, 129.0, 128.7, 128.5, 127.8, 127.5, 127.4, 123.1, 121.0, 118.3, 111.1, 58.5, 55.4, 53.5, 50.3, 41.5, 36.4, 27.0, 26.2, 25.3; LC/MS (ESI+): m/z: calcd for C30H37N3O2: 471.64, [M+H]+; found: 472.60.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596

60
[ 4387-36-4 ]
[ 1924-77-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4587 - 4596

61
[ 1924-77-2 ]
[ 2946-39-6 ]
8-(2-phenylbenzylamino)adenosine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 244 - 248

62
[ 1924-77-2 ]
[ 486-25-9 ]