[ CAS No. 107622-80-0 ] {[proInfo.proName]}

Name: 107622-80-0|(4-Phenoxyphenyl)methanamine|97%
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SKU: A173194
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Quality Control of [ 107622-80-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 107622-80-0 ]

CAS No. :	107622-80-0	MDL No. :	MFCD01310836
Formula :	C₁₃H₁₃NO	Boiling Point :	-
Linear Structure Formula :	H₂NCH₂C₆H₄OC₆H₅	InChI Key :	CCAZAGUSBMVSAR-UHFFFAOYSA-N
M.W :	199.25	Pubchem ID :	2760343
Synonyms :		Chemical Name :	(4-Phenoxyphenyl)methanamine

Safety of [ 107622-80-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 107622-80-0 ]

* 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 [ 107622-80-0 ]
Downstream synthetic route of [ 107622-80-0 ]

[ 107622-80-0 ] Synthesis Path-Upstream 1~6

1
[ 67-36-7 ]
[ 107622-80-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydroxylamine hydrochloride In ethanol; water at 20℃; Inert atmosphere	A solution of 4-phenoxybenzaldehyde (2.0 g, 10 mmol), hydroxylamine hydrochloride (700 mg, 10 mmol), EtOH (20 ml), and water (1 ml) was stirred at room temperature overnight. To the reaction mixture were added 10 N Hci (1 ml) and of Pd/C (10percent on carbon, 320 mg) and was stirred under hydrogen for 30 min. The reaction mixture was filtrated through Celite and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a white solid (1.5 g, 75percent yield).
75%	Stage #1: With hydroxylamine hydrochloride In ethanol; water at 20℃; Stage #2: With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol; water for 0.5 h;	A solution of 4-phenoxybenzaldehyde (2.0 g, 10 mmol), hydroxylamine hydrochloride (700 mg, 10 mmol), EtOH (20 ml), and water (1 ml) was stirred at room temperature overnight. To the reaction mixture were added 10 N HCl (1 ml) and of Pd/C (10percenton carbon, 320 mg) and was stirred under hydrogen for 30 min. The reaction mixture was filtrated through Celite and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a white solid (1.5 g, 75percent yield).

Reference： [1] Patent: WO2017/100668, 2017, A1, . Location in patent: Page/Page column 164
[2] Patent: WO2018/103058, 2018, A1, . Location in patent: Page/Page column 164

2
[ 3096-81-9 ]
[ 107622-80-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 5%-palladium/activated carbon; hydrogen In methanol for 3 h; Inert atmosphere	4-Phenoxybenzonitrile (200 mg, 1.00 mmol) was dissolved in 8 mL MeOH and 5percent Pd/C (0.2 equiv, 400 mg) was added. The reaction was stirred for 3 h under an H2 atmosphere and filtered through celite. Purification by pTLC with 10percent MeOH, 2percent Et3N in DCM afforded 4-phenoxybenzylamine as a white solid (179 mg,88percent). 42 (1.1 equiv, 22 mg) was dissolved in toluene with 2,5-dimethoxyaniline (1 equiv, 8 mg), BINAP (0.3 equiv, 11 mg),Pd(OAc)2 (0.15 equiv, 2 mg) and Cs2CO3 (2.5 equiv, 46 mg) and the mixture was stirred for 15 h at 105 °C. The solvent was removed and the crude product was filtered through silica, eluting with EtOAc. Final purification by pTLC with 50percent EtOAc in hexane afforded 34 as colorless oil (12.4 mg, 48percent).

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 3971 - 3981
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 14, p. 2344 - 2356

3
[ 1194-02-1 ]
[ 107622-80-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 14, p. 2344 - 2356

4
[ 2215-77-2 ]
[ 107622-80-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1428 - 1436

5
[ 1706-12-3 ]
[ 107622-80-0 ]

Reference： [1] Pharmaceutical Bulletin, 1957, vol. 5, p. 397,399

6
[ 36881-42-2 ]
[ 100-97-0 ]
[ 107622-80-0 ]

Reference： [1] Pharmaceutical Bulletin, 1957, vol. 5, p. 397,399

[ 107622-80-0 ] Synthesis Path-Downstream 1~104

1
[ 1722-12-9 ]
[ 107622-80-0 ]
[ 101569-69-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 605,607
Chem.Abstr.,1960,p. 19690

2
[ 36881-42-2 ]
[ 100-97-0 ]
[ 107622-80-0 ]

Reference： [1]Pharmaceutical Bulletin,1957,vol. 5,p. 397,399

3
[ 107622-80-0 ]
[ 53114-57-1 ]
[ 107774-30-1 ]

Reference： [1]Pharmaceutical Bulletin,1957,vol. 5,p. 397,399

4
[ 107622-80-0 ]
[ 122801-52-9 ]
2-(4-Phenoxy-phenyl)-5-p-tolyl-pyridine [ No CAS ]

Reference： [1]Synthesis,1996,p. 372 - 376

5
[ 75-44-5 ]
[ 107622-80-0 ]
[ 56651-61-7 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2344 - 2356

6
[ 3096-81-9 ]
[ 107622-80-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 5%-palladium/activated carbon; hydrogen; In methanol; for 3h;Inert atmosphere;	4-Phenoxybenzonitrile (200 mg, 1.00 mmol) was dissolved in 8 mL MeOH and 5% Pd/C (0.2 equiv, 400 mg) was added. The reaction was stirred for 3 h under an H2 atmosphere and filtered through celite. Purification by pTLC with 10% MeOH, 2% Et3N in DCM afforded 4-phenoxybenzylamine as a white solid (179 mg,88%). 42 (1.1 equiv, 22 mg) was dissolved in toluene with 2,5-dimethoxyaniline (1 equiv, 8 mg), BINAP (0.3 equiv, 11 mg),Pd(OAc)2 (0.15 equiv, 2 mg) and Cs2CO3 (2.5 equiv, 46 mg) and the mixture was stirred for 15 h at 105 C. The solvent was removed and the crude product was filtered through silica, eluting with EtOAc. Final purification by pTLC with 50% EtOAc in hexane afforded 34 as colorless oil (12.4 mg, 48%).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3971 - 3981
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 2344 - 2356

7
[ 107622-80-0 ]
[ 219626-94-5 ]
[ 219625-03-3 ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 915 - 918
[2]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 1901 - 1913

8
[ 107622-80-0 ]
(R)-3-((S)-1-tert-Butoxycarbonylamino-2-phenyl-ethyl)-oxirane-2-carboxylic acid ethyl ester [ No CAS ]
(2R,3R,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-2-(4-phenoxy-benzylamino)-5-phenyl-pentanoic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1331 - 1334

9
[ 463-71-8 ]
[ 107622-80-0 ]
[ 21584-72-5 ]
4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid 4-phenoxy-benzylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4513 - 4523

10
[ 107622-80-0 ]
[ 21584-72-5 ]
[ 530-62-1 ]
4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid 4-phenoxy-benzylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4513 - 4523

11
[ 107622-80-0 ]
2-(3-ethoxycarbonyloxycarbonyl-4-methoxy-benzyl)-butyric acid ethyl ester [ No CAS ]
[ 311770-52-2 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3581 - 3599

12
[ 107622-80-0 ]
[ 679404-36-5 ]
3-(5-amino-7-oxo-6,7-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-N-(4-phenoxy-benzyl)-benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1709 - 1718

13
[ 107622-80-0 ]
[ 87-42-3 ]
(4-phenoxy-benzyl)-(9H-purin-6-yl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3165 - 3168

14
[ 107622-80-0 ]
(S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid [ No CAS ]
((S)-1-{(S)-2-Methyl-1-[(S)-2-(4-phenoxy-benzylcarbamoyl)-pyrrolidine-1-carbonyl]-propylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

15
[ 848779-64-6 ]
[ 102-09-0 ]
[ 107622-80-0 ]
N-(4-phenoxybenzyl)-N'-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-yl]urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2752 - 2757

16
[ 690265-60-2 ]
[ 102-09-0 ]
[ 107622-80-0 ]
1-(4-phenoxy-benzyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2752 - 2757

17
[ 612085-99-1 ]
[ 107622-80-0 ]
3-cyano-5-methyl-4-(4-phenoxy-benzylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 628 - 632

18
[ 4318-42-7 ]
[ 32315-10-9 ]
[ 107622-80-0 ]
[ 76-05-1 ]
4-isopropyl-piperazine-1-carboxylic acid 4-phenoxy-benzylamide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5303 - 5308

19
[ 32315-10-9 ]
[ 51207-66-0 ]
[ 107622-80-0 ]
[ 76-05-1 ]
(S)-2-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid 4-phenoxy-benzylamide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5303 - 5308

20
[ 32315-10-9 ]
[ 107622-80-0 ]
[ 76-05-1 ]
[ 21043-40-3 ]
4-cyclopentyl-piperazine-1-carboxylic acid 4-phenoxy-benzylamide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5303 - 5308

21
[ 107622-80-0 ]
[ 311770-42-0 ]
[ 311770-52-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8405 - 8414
[2]Patent: EP1184366,2002,A1 .Location in patent: Example 10

22
[ 107622-80-0 ]
[ 70-34-8 ]
C₁₉H₁₅N₃O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5652 - 5655

23
[ 107622-80-0 ]
C₁₉H₁₃N₃O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5652 - 5655

24
[ 107622-80-0 ]
2-[4-methoxy-3-(4-phenoxy-benzylcarbamoyl)-benzyl]-butyric acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8405 - 8414

25
[ 1194-02-1 ]
[ 107622-80-0 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2344 - 2356

26
[ 107622-80-0 ]
1-((1R,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-1-methyl-3-(4-phenoxy-benzyl)-urea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2344 - 2356

27
[ 108-95-2 ]
pentacarbonyl(3-cyclohex-1-enyl-1-ethoxy-2-propyn-1-ylidene)tungsten [ No CAS ]
[ 107622-80-0 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2344 - 2356

28
[ 1706-12-3 ]
[ 107622-80-0 ]

Reference： [1]Pharmaceutical Bulletin,1957,vol. 5,p. 397,399

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 81C N-(4-Phenoxybenzyl)amine The compound resulting from Example 81B (6.7 g, 20.4 mmol), hydrazine (2.1 mL, 35 wt. % in water) and 130 mL absolute ethanol were stirred at reflux for 4 hours. After cooling to room temperature, the solid present was filtered and air dried briefly. The solid was then partitioned between 1N KOH and methylene chloride. The layers were separated and the aqueous layer was extracted 2 more times with methylene chloride. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and evaporated in vacuo to afford the title compound (2.7 g) as a clear oil. 1 H-NMR (300 MHz, CDCl3) delta 1.48 (s, 2H), 3.87 (s, 2H), 7.00 (m, 3H), 7.10 (t, 1H), 7.30 (m, 5H). MS (DCl/NH3) m/e 200 (M+H)+, 217 (M+NH4)+.
		EXAMPLE 64C N-(4-Phenoxybenzyl)amine The compound resulting from Example 64B (6.7 g, 20.4 mmol), hydrazine (2.1 mL, 35 wt. % in water) and 130 mL absolute ethanol were stirred at reflux for 4 hours. After cooling to room temperature, the solid present was filtered and air dried briefly. The solid was then partitioned between 1N KOH and methylene chloride. The layers were separated and the aqueous layer was extracted 2 more times with methylene chloride. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and evaporated in vacuo to afford the title compound (2.7 g) as a clear oil. 1 H NMR (300 MHz, CDCl3) delta1.48 (s, 2H), 3.87 (s, 2H), 7.00 (m, 3H), 7.10 (t, 1H), 7.30 (m, 5H). MS (DCl/NH3) m/e 200 (M+H)+, 217 (M+H+NH3)+.

30
[ 107622-80-0 ]
N-[2-(3-fluorophenyl)ethyl]-N'-isoquinolin-5-ylurea [ No CAS ]
N-isoquinolin-5-yl-N'-(4-phenoxybenzyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene;	EXAMPLE 4 N-isoquinolin-5-yl-N'-(4-phenoxybenzyl)urea The title compound was prepared using <strong>[107622-80-0]4-phenoxybenzylamine</strong>, DBU, the product from Example 1A and the procedure described in Example 1B. 1H NMR(300MHz, d6-DMSO) delta 9.30 (s, 1H), 8.75 (s, 1H), 8.58 (d, 1H), 8.31 (d, 1H), 7.92 (d, 1H), 7.75 (d, 1H), 7.60 (t, 1H), 7.40 (m, 4H), 7.18-6.95 (m, 6H), 4.38 (d, 2H); MS (DCI/NH3) m/z 369 (M+H)+.
	With 1,8-diazabicyclo[5.4.0]undec-7-ene;	EXAMPLE 4 N-isoquinolin-5-yl-N'-(4-phenoxybenzyl)urea The title compound was prepared using <strong>[107622-80-0]4-phenoxybenzylamine</strong>, DBU, the product from Example 1A and the procedure described in Example 1B. 1H NMR (300 MHz, d6-DMSO) delta 9.30 (s, 1H), 8.75 (s, 1H), 8.58 (d, 1H), 8.31 (d, 1H), 7.92 (d, 1H), 7.75 (d, 1H), 7.60 (t, 1H), 7.40 (m, 4H), 7.18-6.95 (m, 6H), 4.38 (d, 2H); MS (DCI/NH3) m/z 369 (M+H)+.
	With 1,8-diazabicyclo[5.4.0]undec-7-ene;	EXAMPLE 4 N-isoquinolin-5-yl-N'-(4-phenoxybenzyl)urea The title compound was prepared using <strong>[107622-80-0]4-phenoxybenzylamine</strong>, DBU, the product from Example 1A and the procedure described in Example 1B. 1H NMR (300 MHz, d6-DMSO) delta 9.30 (s, 1H), 8.75 (s, 1H), 8.58 (d, 1H), 8.31 (d, 1H), 7.92 (d, 1H), 7.75 (d, 1H), 7.60 (t, 1H), 7.40 (m, 4H), 7.18-6.95 (m, 6H), 4.38 (d, 2H); MS (DCI/NH3) m/z 369 (M+H)+.

Reference： [1]Patent: US2003/158188,2003,A1
[2]Patent: US6933311,2005,B2
[3]Patent: US2004/157849,2004,A1

31
[ 461-72-3 ]
[ 107622-80-0 ]
[ 477583-00-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 104 2-(4-methyl-2,5-dioxo-4-imidazolidinyl)-N-(4-phenoxybenzyl)acetamide Hydantoin 103a (50 mg, 0.30 mmol) was coupled to <strong>[107622-80-0]4-phenoxybenzylamine</strong> using general coupling method A to give 45 mg of the product hydantoin. MS found:(M+H)+=354.

Reference： [1]Patent: US2003/130273,2003,A1

32
[ 7304-32-7 ]
[ 107622-80-0 ]
[ 247569-63-7 ]
[ 247567-34-6 ]

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 108 2-Fluoro-5-nitro-N-(4-phenoxybenzyl)benzamide (1.22 g) was obtained as yellow powders from 2-fluoro-5-nitrobenzoic acid (1.00 g) and <strong>[107622-80-0]4-phenoxybenzylamine</strong> (1.13 g) in a manner similar to Preparation 55. NMR (DMSO-d6, delta): 4.49 (2H, d, J=6 Hz), 6.95-7.05 (4H, m), 7.13 (1H, dd, J=7.5, 7.5 Hz), 7.32-7.45 (4H, m), 7.63 (1H, dd, J=9, 9 Hz), 8.37-8.50 (2H, m),9.18 (1H, t, J=6 Hz); Mass m/z: 365(M+).

Reference： [1]Patent: US6384080,2002,B1

33
[ 877149-15-0 ]
[ 107622-80-0 ]
5-bromo-7-methyl-2-(4-phenoxybenzyl)-2,3-dihydroisoindol-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In toluene; at 95℃; for 12h;	[0201] 4-Bromo-2-bromomethyl-6-methylbenzoic acid methyl ester (762 mg, 2.37 mmol), 4-phenoxy benzylamine (0.543 mL, 3.56 mmol) and K2CO3 (981 mg, 7.10 mmol) were stirred in toluene (10 mL) at 95 C for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2-SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford a yellow oil (650 mg). .H NMR (300 MHz, CDCI3): 5 7.35-7.38 (m, 4H), 7.32 (s, 1H), 7.26-7.29 (m, 1H), 7.15 (t, 1H), 6.99 (t. 4H), 4.74 (s, 2H), 4.23 (s, 2H), 2.75 (s, 3H).

Reference： [1]Patent: WO2006/20879,2006,A1 .Location in patent: Page/Page column 70

34
[ 107622-80-0 ]
3-Hydroxy-4-methoxy-N-(4'-phenoxybenzyl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 71 3-Hydroxy-4-methoxy-N-(4'-phenoxybenzyl)picolinamide: The procedure of Example 39 was repeated, except that 4-benzyloxyaniline hydrochloride was changed to <strong>[107622-80-0]4-phenoxybenzylamine</strong>. Thus, the title compound was prepared.

Reference： [1]Patent: EP1134214,2001,A1

35
methyl 4-[(3-oxo-8-azabicyclo[3.2.1]oct-8-yl)methyl]-benzoate [ No CAS ]
[ 107622-80-0 ]
methyl 4-[[(3-exo)-3-[[(4-phenoxyphenyl)methyl]amino]-8-azabicyclo[3.2.1]oct-8-yl]methyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; water; for 60.25h;	A solution of methyl 4-[(3-oxo-8-azabicyclo[3.2.1]oct-8-yl)methyl]-benzoate (0.3 g, 1.1 mmol) and 4-phenoxybenzenemethaneamine (0.23 g, 1.15 mmol) in dichloromethane (6.5 mL) was stirred as acetic acid (0.09 g, 1.5 mmol) was added. After 15 minutes, sodium triacetoxyborohydride (0.45 g, 2.15 mmol) was added and the reaction was stirred for 2.5 days. The reaction was treated with a saturated aqueous solution of sodium bicarbonate and extracted with dichlorormethane (2*). The combined organic extracts were washed with water, dried and concentrated. Purification by flash chromatography on silica gel using a gradient of methanol in dichloromethane gave 0.2 g of methyl 4-[[(3-exo)-3-[[(4-phenoxyphenyl)methyl]amino]-8-azabicyclo[3.2.1]oct-8-yl]methyl]benzoate.

Reference： [1]Patent: US2007/155726,2007,A1 .Location in patent: Page/Page column 73

36
[ 107622-80-0 ]
[ 311771-04-7 ]
C₂₉H₃₃NO₅ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 54

37
[ 107622-80-0 ]
[ 311771-05-8 ]
C₃₀H₃₅NO₅ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 58

38
[ 311771-56-9 ]
[ 107622-80-0 ]
C₂₉H₃₃NO₅ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 151

39
[ 107622-80-0 ]
[ 311771-57-0 ]
C₃₀H₃₅NO₅ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 149

40
[ 311771-59-2 ]
[ 107622-80-0 ]
C₂₈H₂₈F₃NO₅ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 153

41
[ 107622-80-0 ]
[ 311770-45-3 ]
C₂₉H₃₃NO₅ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 50

42
[ 107622-80-0 ]
[ 311770-46-4 ]
C₂₇H₂₉NO₆ [ No CAS ]

Reference： [1]Patent: EP1184366,2002,A1 .Location in patent: Example 15

43
[ 107622-80-0 ]
[ 57489-77-7 ]
[ 1091598-94-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5694 - 5697

44
[ 2215-77-2 ]
[ 107622-80-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 1428 - 1436

45
[ 107622-80-0 ]
[ 2004-06-0 ]
[ 722505-26-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 1428 - 1436

46
[ 842137-60-4 ]
[ 107622-80-0 ]
[ 842137-61-5 ]

Yield	Reaction Conditions	Operation in experiment
81%		To a solution of 4- [ (3-CYCLOPENTYLPROPANOYL) (2, 2-dimethyl-4-oxo-4H-1, 3-benzodioxin-6- yl) amino] methyl}benzoic acid (212 mg) in THF (2 mL) was added NMM (57 mg). The mixture was chilled at 0C and isobutyl CHLOROFORMATE was added at once (86 mg). The mixture was stirred for 15 min. at 0C then <strong>[107622-80-0]4-phenoxybenzylamine</strong> (103 mg) was added and the resulting reaction mixture was stirred 3 h at rt. An aqueous solution oh HCl (1N, 2 mL) was added and the resulting mixture was extracted with ET2O. THE combined organic layers were washed with water, brine, dried over MGSO4 filtered and evaporated to give a light yellow oil. Purification by chromatography (SIO2) gave the title compound as a colorless oil (241 mg, 81%). H NMR (CDC13) B 7.56-7. 42 (m, 3H), 7.21-7. 00 (M, 6H), 6.95-6. 67 (m, 7H), 6.21 (t, J=4. 9 Hz, 1H), 4.69 (s, 2H), 4.42 (s, 1H), 4.40 (s, 1H), 1.87 (t, J=7. 2 Hz, 2H), 1.54 (s, 6H), 1.48-1. 14 (m, 9H), 0.85-0. 64 (m, 2M). M - (ESI) : 633. 0; M- (ESI) : 631. 0. HPLC, Rt: 5.3 min (purity : 97.7%).

Reference： [1]Patent: WO2005/11685,2005,A1 .Location in patent: Page/Page column 52-53

47
[ 933-20-0 ]
[ 107622-80-0 ]
C₁₆H₁₄ClN₅O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5229 - 5232
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 7557 - 7574

48
[ 1251921-57-9 ]
[ 107622-80-0 ]
[ 1251921-58-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol; at 80℃; for 48h;Inert atmosphere;	A mixture of ethyl 5-(3,5-dichloro-4-hydroxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.3003 g, 0.990 mmol) and <strong>[107622-80-0]4-phenoxybenzylamine</strong> (0.5922 g, 2.97 mmol) in ethanol (10 mL) was stirred at 80 C. under nitrogen for 2 d. The mixture was partitioned between dilute aqueous HCl (50 mL) and ethyl acetate (75 mL). The aqueous layer was extracted further with ethyl acetate (50 mL) and the combined extracts were washed with brine (30 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2) to give 0.4235 g (94%) of the title compound as a white solid.

Reference： [1]Patent: US2010/267725,2010,A1 .Location in patent: Page/Page column 25

49
[ 107622-80-0 ]
[ 96568-02-4 ]
[ 1185095-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃;	The thus obtained crude 2,6-dichloro-5-fluoronicotinic acid chloride was dissolved in 20 ml ofTHF. A mixture solution of 1.0g of <strong>[107622-80-0]4-phenoxybenzylamine</strong>, 2.0 g of triethylalmine and 5 ml of THF was then added dropwise to the above obtained solution at 0C The obtained solution was stirred at a room temperature for 4 hours. Thereafter, diluted hydrochloric acid was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with a sodium bicarbonate aqueous solution, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 1.25 g of N-(4-phenoxyphenyl)methyl-2,6-dichloro-5-fluoronicotinic acid amide.N-(4-phenoxyphenyl)methyl-2,6-dichloro-5-fluoronicotinic acid amide [Show Image] 1H-NMR (CDCl3) delta: 4.64 (2H, d, J = 5.6 Hz), 6.90 (1H, br s), 6.98-7.03 (4H, m), 7.10-7.15 (1H, m), 7.30-7.37 (4H, m), 8.04 (1H, d, J = 7.5 Hz).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 78-79

50
[ 5345-47-1 ]
[ 107622-80-0 ]
[ 1185088-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 4h;	Production example 3 0.88 g of a BOP reagent and 0.40 g of triethylamine were successively added to a mixture of 0.28 g of 2-aminonicotinic acid, 0.40 g of <strong>[107622-80-0]4-phenoxybenzylamine</strong> and 10 ml of DMF. The obtained mixture was stirred at a room temperature for 4 hours. Thereafter, ice and a saline solution were successively added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was further washed with a saline solution 3 times, and it was then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. 0.80 g of the obtained residue was subjected to silica gel column chromatography, so as to obtain 0.62 g of N-(4-phenoxyphenyl)methyl-2-aminonicotinic acid amide (hereinafter referred to as the present compound 3).The present compound 3 [Show Image] 1H-NMR (DMSO-D6) delta: 4.42 (2H, d, J = 5.9 Hz), 6.59 (1H, dd, J = 7.8, 4.9 Hz), 6.97-6.99 (4H, m), 7.08 (2H, br), 7.10-7.13 (1H, m), 7.32-7.40 (4H, m), 7.95 (1H, dd, J = 7.8, 1.7 Hz), 8.08 (1H, dd, J = 4.9, 1.7 Hz), 8.98 (1H, t, J = 5.9 Hz).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 58

51
[ 107622-80-0 ]
[ 171178-50-0 ]
[ 1185095-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 48h;	A mixture of 1.0 g of 2,6-difluoronicotinic acid, 1.4 g of WSC, 1.4 g of <strong>[107622-80-0]4-phenoxybenzylamine</strong> and 5 ml of DMF was stirred at a room temperature for 2 days. Thereafter, a sodium bicarbonate aqueous solution was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.90 g of N-(4-phenoxyphenyl)methyl-2,6-difluoronicotinic acid amide. [Show Image] 1H-NMR (CDCl3) delta: 4.64 (2H, d, J = 5.4 Hz), 6.97-7.03 (6H, m), 7.09-7.14 (1H, m), 7.30-7.36 (4H, m), 8.69-8.76 (1H, m).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 73-74

52
[ 38496-18-3 ]
[ 107622-80-0 ]
[ 1185095-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 100℃; for 4h;	A mixture of 1.0 g of 2,6-dichloronicotinic acid, 1.3 g of WSC, 1.3 g of <strong>[107622-80-0]4-phenoxybenzylamine</strong> and 5 ml of DMF was stirred at 100C for 4 hours. After, water was added to the reaction mixture, it was then extracted with ethyl acetate. The organic layer was successively washed with water and a saturated saline solution, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.37 g of N-(4-phenoxyphenyl)methyl-2,6-dichloronicotinic acid amide. [Show Image] 1H-NMR (CDCl3) delta: 4.64 (2H, d, J = 5.8 Hz), 6.79 (1H, br s), 6.98-7.03 (4H, m), 7.10-7.14 (1H, m), 7.31-7.37 (4H, m), 7.39 (1H, d, J = 8.0 Hz), 8.15 (1H, d, J = 8.0 Hz).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 82

53
[ 849805-27-2 ]
[ 107622-80-0 ]
[ 1185089-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	Production example 46 0.13 g of 2-amino-6-methoxymethylnicotinic acid, 0.20 g of <strong>[107622-80-0]4-phenoxybenzylamine</strong>, 0.27 g of triethylamine and 0.55 g of a BOP reagent were added to 2 ml of DMF. The obtained mixture was stirred at a room temperature for 16 hours. Thereafter, water was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with water, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.17 g of N-(4-phenoxyphenyl)methyl-2-amino-6-methoxymethylnicotinic acid amide (hereinafter referred to as the present compound 62).The present compound 62 [Show Image] 1H-NMR (CDCl3) delta: 3.45 (3H, s), 4.40 (2H, s), 4.57 (2H, d, J = 5.8 Hz), 6.23-6.30 (1H, br m), 6.40 (2H, br s), 6.70 (1H, d, J = 8.0 Hz), 6.98-7.02 (4H, m), 7.09-7.13 (1H, m), 7.29-7.36 (4H, m), 7.61 (1H, d, J = 8.0 Hz).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 83-84

54
[ 175155-53-0 ]
[ 107622-80-0 ]
[ 1185088-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	Production example 15 A mixture of 0.50 g of 2,6-diaminonicotinic acid, 0.57 g of 1-hydroxybenzotriazole, 0.82 g of WSC, 0.65 g of <strong>[107622-80-0]4-phenoxybenzylamine</strong>, 0.50 g of triethylamine and 4 ml of DMF was stirred at a room temperature for 1 day. Thereafter, a sodium bicarbonate aqueous solution was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.37 g of N-(4-phenoxyphenyl)methyl-2,6-diaminonicotinic acid amide (hereinafter referred to as the present compound 17).The present compound 17 [Show Image] 1H-NMR (CDCl3) delta: 4.50 (2H, br s), 4.54 (2H, d, J = 5.6 Hz), 5.78 (1H, dd, J = 8.5, 1.2 Hz), 6.02 (1H, br s), 6.45 (2H, br s), 6.97-7.02 (4H, m), 7.08-7.13 (1H, m), 7.29-7.40 (5H, m).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 64

55
[ 107622-80-0 ]
[ 30529-70-5 ]
[ 1185095-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 - 100℃;	0.50 g of 2-chloro-6-methyl-nicotinic acid, 0.64 g of <strong>[107622-80-0]4-phenoxybenzylamine</strong> and 0.64 g of WSC were mixed with 5 ml of DMF. The obtained mixture was stirred under heating at 100C for 5 minutes, and it was then stirred at a room temperature for 1 day. Thereafter, water was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with a sodium bicarbonate aqueous solution, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.60 g of N-(4-phenoxyphenyl)methyl-2-chloro-6-methyl-nicotinic acid amide. [Show Image] 1H-NMR (CDCl3) delta: 2.57 (3H, s), 4.64 (2H, d, J = 5.8 Hz), 6.87 (1H, br s), 6.98-7.02 (4H, m), 7.09-7.13 (1H, m), 7.20 (1H, d, J = 7.7 Hz), 7.31-7.37 (4H, m), 8.09 (1H, d, J = 7.7 Hz).

Reference： [1]Patent: EP2248423,2010,A1 .Location in patent: Page/Page column 70

56
4-(4-chlorophenyl)thiazole-2-carboxylic acid [ No CAS ]
[ 107622-80-0 ]
4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid 4-phenoxy-benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		Compound 54. 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid 4-phenoxy-benzylamide (B250307) 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid (49 mg, 0.18 mmol) was dissolved in THF (5 mL), followed by addition of CDI (34 mg, 0.21 mmol). The slurry mixture was stirred at RT for 1 hour. 4-Phenoxybenzylamine (41 mg, 0.21 mmol) dissolved in THF (2 mL) was added to it. The reaction was continued at RT for 24 hours. After removal of the solvent, the residue was dissolved in dichloromethane. After filtration through a pad of silica eluted with chloroform and concentration, the residue was applied on chromatotron (silica) eluted with chloroform to afford one major component with Rf=0.19 (chloroform, silica). It was an off-white semisolid (30 mg, Y=40%). The structure of the compound was confirmed by NMR and MS.

Reference： [1]Patent: US2007/32531,2007,A1 .Location in patent: Page/Page column 45

57
[ 302-79-4 ]
[ 107622-80-0 ]
[ 1311276-20-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4378 - 4387

58
[ 1333406-57-7 ]
[ 107622-80-0 ]
[ 1333405-58-5 ]

Yield	Reaction Conditions	Operation in experiment
15.52%	With acetic acid; at 130 - 135℃; for 48h;Sealed tube;	General procedureA mixture of 1 H-benzimidazole-5-carboxylic acid dimethylaminomethylene-hydrazide (1 eq) and substituted benzyl amine (2eq) in glacial acetic acid (5ml_) was heated in a sealed tube at 130-135C for 48h. The solvent was evaporated in vacuo to afford crude compound. The crude compound was purified by conducting two successive preparative TLC procedures a) 7% methanol in chloroform followed by, b) 7% methanol in ethyl acetate +2% ammonia solution as eluent to afford the product.Example 10: 5-(4-(4-Phenoxybenzyl)-4H-1 ,2,4-triazol-3-yl)-1 H-benzofdlimidazoleThe compound was synthesized starting from H-benzimidazole-5-carboxylic acid dimethylaminomethylene-hydrazide (203mg, .88mmol), 4-phenoxy benzyl amine (350mg, 1 .76mmol), acetic acid (5mL) as described above. Yield: 50mg (15.52%)MS m/z: 368.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): delta 5.36 (s, 2H); 6.91 -6.95 (br m, 4H); 7.04-7.07 (m, 2H); 7.1 1 -7.15 (m, 1 H); 7.35-7.43 (br m, 3H); 7.68-7.70 (br m, 1 H); 7.78 (s,1 H); 8.31 (s, 1 H); 8.68 (s, 1 H); HPLC (METHOD [A]): rt 1 1.12 min (97.3%)

Reference： [1]Patent: WO2011/107530,2011,A2 .Location in patent: Page/Page column 92; 103

59
[ 107622-80-0 ]
[ 1373889-73-6 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 316 - 322

60
[ 107622-80-0 ]
[ 1373889-35-0 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 316 - 322

61
[ 107622-80-0 ]
[ 105-34-0 ]
[ 566926-15-6 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 316 - 322

62
[ 410544-37-5 ]
[ 107622-80-0 ]
[ 1407998-50-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9492 - 9509

63
C₂₈H₃₄NO₈PolSi [ No CAS ]
[ 107622-80-0 ]
C₄₁H₄₅N₂O₈PolSi [ No CAS ]

Reference： [1]Patent: WO2014/28946,2014,A2 .Location in patent: Page/Page column 89

64
[ 107622-80-0 ]
[ 53355-55-8 ]
[ 1622426-84-9 ]

Yield	Reaction Conditions	Operation in experiment
21 mg	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).
	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene (10equiv, 20% in toluene) at 0 C. The reaction mixture was stirred at roomtemperature for 1 h. The solvent was removed under reduced pressureand the crude carbamoyl chloride was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate amine (1.0 equiv) or alcohol (1 equiv) andEt3N (1.2 equiv) were dissolved in CH2Cl2 (0.5 M) and cooled to 0 C.The crude carbamoyl chloride was added dropwise and the reactionmixture was stirred at room temperature for 16 h. The mixture wasdiluted with EtOAc, washed with saturated aqueous NaCl, and driedover Na2SO4. Evaporation under reduced pressure yielded the crudecoupling product that was purified by flash chromatography (SiO2).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3807 - 3813
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1693 - 1703

65
[ 67514-62-9 ]
[ 107622-80-0 ]
[ 1622426-85-0 ]

Yield	Reaction Conditions	Operation in experiment
14 mg	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).
	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene (10equiv, 20% in toluene) at 0 C. The reaction mixture was stirred at roomtemperature for 1 h. The solvent was removed under reduced pressureand the crude carbamoyl chloride was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate amine (1.0 equiv) or alcohol (1 equiv) andEt3N (1.2 equiv) were dissolved in CH2Cl2 (0.5 M) and cooled to 0 C.The crude carbamoyl chloride was added dropwise and the reactionmixture was stirred at room temperature for 16 h. The mixture wasdiluted with EtOAc, washed with saturated aqueous NaCl, and driedover Na2SO4. Evaporation under reduced pressure yielded the crudecoupling product that was purified by flash chromatography (SiO2).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3807 - 3813
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1693 - 1703

66
C₅H₂ClN₃O [ No CAS ]
[ 107622-80-0 ]
[ 1622426-86-1 ]

Yield	Reaction Conditions	Operation in experiment
12 mg	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).
	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene (10equiv, 20% in toluene) at 0 C. The reaction mixture was stirred at roomtemperature for 1 h. The solvent was removed under reduced pressureand the crude carbamoyl chloride was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate amine (1.0 equiv) or alcohol (1 equiv) andEt3N (1.2 equiv) were dissolved in CH2Cl2 (0.5 M) and cooled to 0 C.The crude carbamoyl chloride was added dropwise and the reactionmixture was stirred at room temperature for 16 h. The mixture wasdiluted with EtOAc, washed with saturated aqueous NaCl, and driedover Na2SO4. Evaporation under reduced pressure yielded the crudecoupling product that was purified by flash chromatography (SiO2).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3807 - 3813
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1693 - 1703

67
[ 107622-80-0 ]
6-[(2,5-dimethoxyphenyl)amino]-N-(4-phenoxybenzyl)picolinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3971 - 3981

68
[ 107622-80-0 ]
6-[(3,6-dioxocyclohexa-1,4-dien-1-yl)amino]-N-(4-phenoxybenzyl)picolinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3971 - 3981

69
[ 21190-87-4 ]
[ 107622-80-0 ]
6-bromo-N-(4-phenoxybenzyl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 6-chloro-1-hydroxybenzotriazole; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	General procedure: To a 0.2 M solution of amine (0.1-10 mmol, 1 equiv) and carboxylic acid (1 equiv) in DCM was added Cl-HOBt (1.05 equiv)and Et3N (1.3 equiv) followed by EDC-HCl (1.2 equiv). The mixture was stirred at rt for 12 h. The crude mixture was diluted with DCM and washed once with 1 M HCl, once with satd NaHCO3 and once with brine. The DCM solution was evaporated to afford the product with >90% purity. The product was recrystallized from Et2O/hexane or purified by silica gel chromatography if necessary. Yields were typically >75%.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3971 - 3981

70
[ 98-98-6 ]
[ 107622-80-0 ]
N-(4-phenoxybenzyl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 6-chloro-1-hydroxybenzotriazole; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere;	General procedure: To a 0.2 M solution of amine (0.1-10 mmol, 1 equiv) and carboxylic acid (1 equiv) in DCM was added Cl-HOBt (1.05 equiv)and Et3N (1.3 equiv) followed by EDC-HCl (1.2 equiv). The mixture was stirred at rt for 12 h. The crude mixture was diluted with DCM and washed once with 1 M HCl, once with satd NaHCO3 and once with brine. The DCM solution was evaporated to afford the product with >90% purity. The product was recrystallized from Et2O/hexane or purified by silica gel chromatography if necessary. Yields were typically >75%.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3971 - 3981

71
[ 107622-80-0 ]
(R)-N-(4-phenoxybenzyl)-2-acetamido-3-methoxypropionamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3655 - 3666

72
[ 107622-80-0 ]
C₁₇H₂₀N₂O₃*ClH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3655 - 3666

73
[ 3262-72-4 ]
[ 107622-80-0 ]
(R)-N-4'-(3''-trifluoromethoxyphenoxy)benzyl-2-tert-butoxycarbonylamino-3-hydroxypropionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -78 - 20℃;	General procedure: To a cooled anhydrous THF solution (-78 C, dry ice acetone bath) of (R)-tert-Boc-D-serine ((R)-27)([C] ~ 0.1 M) were successively added N-methylmorpholine (NMM) (1.0-1.5equiv), stirred for 2 min, isobutylchloroformate (IBCF) (1.1-1.3 equiv), stirred for 5 min, and then the desired benzylamine (22-26) (1.0-1.2 equiv) in anhydrous THF. Upon addition the reaction mixture was allowed to warm to room temperature and further stirred (2-3 h). The salts were filtered over a Celite pad and rinsed with THF and the filtrate was concentrated in vacuo. The residue obtained was purified bycolumn chromatography on SiO2 giving the desired product as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3655 - 3666

74
[ 3262-72-4 ]
[ 107622-80-0 ]
(R)-N-(4'-phenoxybenzyl)-2-tert-butoxycarbonylamino-3-methoxypropionamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3655 - 3666

75
[ 107622-80-0 ]
[ 619-66-9 ]
4-formyl-N-(4-phenoxybenzyl)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 61 - 81

76
[ 107622-80-0 ]
ethyl 2-ethyl-3-[4-(N-((4-phenoxy)benzyl)benzamide)]propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 61 - 81

77
[ 107622-80-0 ]
2-ethyl-3-[4-(N-((4-phenoxy)benzyl)benzamide)]propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 61 - 81

78
[ 107622-80-0 ]
ethyl (E)-4-[N-((4-phenoxy)benzyl)benzamide]-α-ethylcinnamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 61 - 81

79
[ 107622-80-0 ]
(E)-4-[N-((4-phenoxy)benzyl)benzamide]-α-ethylcinnamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 61 - 81

80
2-(dibenzo[b,d]thiophen-2-yl)imidazo[1,2-a]pyridine-3-carboxylic acid [ No CAS ]
[ 107622-80-0 ]
C₃₃H₂₃N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 12h;	General procedure: To a solution of 2-(dibenzo[b,d]thiophen-2-yl)imidazo[1,2-a]pyridine-3-carboxylic acid 5 (2.83mmol) in anhydrous DMF (10mL) were added 1-[3-(dimethyl amino)propyl]-3-ethylcarbodiimide (EDCI, 3.84mmol), 1-hydroxybenzo triazole (HOBt, 1.54mmol), triethyl amine (TEA, 5.12mmol) and 6a-s (2.56mmol) at room temperature, and the resulting solution was heated at 80C with stirring. After 12h, the reaction mixture was cooled to room temperature and evaporated. Water (50mL) was added into the crude residue, the resulting solid was collected by filtration, and the filtered cake was washed with water (50mL) and dried to afford crude product. The resulting crude compound was purified by column chromatography over silica gel (n-hexane/EtOAc=1:1) to give 7a-s as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3135 - 3140

81
[ 107622-80-0 ]
[ 61220-49-3 ]
C₂₄H₂₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; sodium iodide; In tetrahydrofuran; at 100℃; for 0.333333h;Microwave irradiation;	General procedure: One equivalent of intermediate 14a or 14b was dissolved in THF and 1.5 eq of the proper amine, 1.5 eq of TEA, 1.5 eq of NaI and 0.3 eq of (CH3COO)2Pd were added to this solution. The reaction was conducted under muW, at 100C, for 20min. The resulting mixture was filtered through Celite, dried in vacuo and reconstituted in DCM. The organic phase was washed with water (3×50mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by column chromatography using DCM/MeOH (9:1 v/v) as mobile phase giving derivative 15 in 38% yield and intermediates 16a-i in 55-75% yield.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 773 - 781

82
[ 74272-78-9 ]
[ 107622-80-0 ]
2,3-dibenzyloxy-N-(4-phenoxyphenyl)methylbenzamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 25 - 37

83
[ 74272-78-9 ]
[ 107622-80-0 ]
N-(4-phenoxyphenyl)methyl-2,3-dihydroxy-benzamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 25 - 37

84
[ 67-36-7 ]
[ 107622-80-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydroxylamine hydrochloride; In ethanol; water; at 20℃;Inert atmosphere;	A solution of 4-phenoxybenzaldehyde (2.0 g, 10 mmol), hydroxylamine hydrochloride (700 mg, 10 mmol), EtOH (20 ml), and water (1 ml) was stirred at room temperature overnight. To the reaction mixture were added 10 N Hci (1 ml) and of Pd/C (10% on carbon, 320 mg) and was stirred under hydrogen for 30 min. The reaction mixture was filtrated through Celite and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a white solid (1.5 g, 75% yield).
75%		A solution of 4-phenoxybenzaldehyde (2.0 g, 10 mmol), hydroxylamine hydrochloride (700 mg, 10 mmol), EtOH (20 ml), and water (1 ml) was stirred at room temperature overnight. To the reaction mixture were added 10 N HCl (1 ml) and of Pd/C (10%on carbon, 320 mg) and was stirred under hydrogen for 30 min. The reaction mixture was filtrated through Celite and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a white solid (1.5 g, 75% yield).

Reference： [1]Patent: WO2017/100668,2017,A1 .Location in patent: Page/Page column 164
[2]Patent: WO2018/103058,2018,A1 .Location in patent: Page/Page column 164

85
C₁₆H₁₅ClN₆O [ No CAS ]
[ 107622-80-0 ]
6-methyl-N-((1s,3s)-3-(6-((4-phenoxybenzyl)amino)-9H-purin-9-yl)cyclobutyl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 3h;Heating;	General procedure: A mixture of 5 (1 eq.) and amine (2 eq.) in ethanol was stirred at 85 C for 3 h. The mixture was concentrated and purified by flash column chromatography to give compound 6.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4399 - 4404

86
C₁₃H₁₆NO₄Pol [ No CAS ]
[ 107622-80-0 ]
C₂₆H₂₉N₂O₄Pol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 13530 - 13541

87
[ 7304-32-7 ]
[ 107622-80-0 ]
[ 247567-87-9 ]

Reference： [1]Patent: US6384080,2002,B1

88
[ 311771-56-9 ]
[ 107622-80-0 ]
C₂₇H₂₉NO₅ [ No CAS ]