[ CAS No. 76410-58-7 ] {[proInfo.proName]}

Name: 76410-58-7|(S)-2-Amino-3-(4-boronophenyl)propanoic acid|95%
Brand: Ambeed
SKU: A134259
Price: 8.0 USD
Availability: InStock
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2D 3D

Structure of 76410-58-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 76410-58-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 76410-58-7 ]

SDS Specification

Alternatived Products of [ 76410-58-7 ]

Product Details of [ 76410-58-7 ]

CAS No. :	76410-58-7	MDL No. :	MFCD01075172
Formula :	C₉H₁₂BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NFIVJOSXJDORSP-QMMMGPOBSA-N
M.W :	209.01	Pubchem ID :	150315
Synonyms :	L-p-Boronophenylalanine

Calculated chemistry of [ 76410-58-7 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	55.33
TPSA :	103.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-2.5
Log Po/w (WLOGP) :	-1.68
Log Po/w (MLOGP) :	-2.79
Log Po/w (SILICOS-IT) :	-1.66
Consensus Log Po/w :	-1.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.41
Solubility :	534.0 mg/ml ; 2.55 mol/l
Class :	Highly soluble
Log S (Ali) :	0.86
Solubility :	1530.0 mg/ml ; 7.31 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.76
Solubility :	36.1 mg/ml ; 0.173 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Safety of [ 76410-58-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 76410-58-7 ]

* 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 [ 76410-58-7 ]
Downstream synthetic route of [ 76410-58-7 ]

[ 76410-58-7 ] Synthesis Path-Upstream 1~21

1
[ 119771-23-2 ]
[ 76410-58-7 ]

Yield	Reaction Conditions	Operation in experiment
93.2%	With hydrogenchloride In water; acetone at 55℃; for 1.5 h;	A suspension of (S)-N-Boc-4-boronophenylalanine(5.63 g, 98.5percent pure, 17.9 mmol) in a mixture of acetone (34 ml) and water (3.8 ml) was stirred and added hydrochloric acid (37 percent, 3.8 ml) to form an acidic mixture, and the acidic mixture was stirred at 55°C for 1.5 h. HPLC analysis of the acidic mixture showed the completion of the reaction. The acidic mixture was cooled to room temperature, and the pH value of the acidic mixture was adjusted to pH 1.5 by using sodium hydroxide aqueous solution. The acidic mixture was stirred for 30 min, and the product 4-borono-L-phenylalanine started to precipitate during this period. The pH value of the acidic mixture was readjusted to pH 6.2 by using sodium hydroxide aqueous solution, and the acidic mixture was stirred overnight at room temperature. The acidic mixture was filtered to obtain solid 4-borono-L-phenylalanine.
70.18%	With hydrogenchloride In water; acetone for 4 h; Heating	With reference to the following Reaction Formula IV′, it is the chemical reaction formula of deprotecting the amine terminal of (S)—N-Boc-4-borono-L-phenylalanine to prepare L-BPA. The specific operation method is as follows: A reaction device was set up, using 100 mL three-necked flask. At the temperature of 2030° C., (S)—N-Boc-4-borono-L-phenylalanine (1.80 g, 5.82 mmol, 1.00 eq), water (0.63 mL) and acetone (11.30 mL) were separately added into the flask. Then HCl (17.46 mmol, 1.46 mL, 3.00 eq) was dropwise added into the reaction. After the dropwise addition was completed, the temperature of reaction was risen to 60° C., and the reaction was stirred for 4 hours. HPLC detection indicated that the reaction was already completed. The reaction liquid was concentrated under reduced pressure at 40° C. with most of acetone was rotary evaporated. The temperature was cooled down to 015° C., and the pH value was adjusted to 1.5 by NaOH solution (4M), and the solids started precipitated. The pH value was adjusted continuously to 6.2, and a large amount of white solids were precipitated, stirred for 15 minutes. The white solid was collected by filtration and drip washed with acetone (6 mL), then transferred and dried by rotary evaporating. The resulting white solid L-BPA was obtained (0.85 g, 4.07 mmol, analyzed by HPLC, 70.18percent yield, 98percent purity). The analysis results of the resulting L-BPA by HNMR were described as follows: ¹H NMR: (400 MHz D₂O) δ=7.62 (d, J=7.5 Hz, 2H), 7.22 (d, J=7.9 Hz, 2H), 3.86 (dd, J=5.5, 7.5 Hz, 1H), 3.20-3.13 (m, 1H), 3.05-2.97 (m, 1H).

Reference： [1] Patent: EP2865682, 2015, A1, . Location in patent: Paragraph 0077; 0078
[2] Patent: US2018/155368, 2018, A1, . Location in patent: Paragraph 0123-0128
[3] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

2
[ 164203-33-2 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

3
[ 262604-05-7 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

4
[ 1991-81-7 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235
[2] Patent: US2018/155368, 2018, A1,

5
[ 7732-18-5 ]
[ 262604-04-6 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

6
[ 220400-04-4 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235
[2] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

7
[ 1333-74-0 ]
[ 164203-33-2 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

8
[ 5513-40-6 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

9
[ 183070-41-9 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

10
[ 262604-00-2 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

11
[ 286472-74-0 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

12
[ 257628-00-5 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

13
[ 262604-03-5 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

14
[ 262603-99-6 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

15
[ 866114-96-7 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

16
[ 214491-30-2 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

17
[ 262604-02-4 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

18
[ 262603-98-5 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

19
[ 1333-74-0 ]
[ 262604-05-7 ]
[ 76410-58-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 231 - 235

20
[ 103882-09-3 ]
[ 76410-58-7 ]

Reference： [1] Patent: EP2865682, 2015, A1,
[2] Patent: US2018/155368, 2018, A1,

21
[ 76410-58-7 ]
[ 224824-22-0 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 6, p. 983 - 985
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11046 - 11050[3] Angew. Chem., 2014, vol. 126, # 41, p. 11226 - 11230,5

[ 76410-58-7 ] Synthesis Path-Downstream 1~88

1
[ 64-17-5 ]
[ 76410-58-7 ]
[ 77374-24-4 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

2
[ 19393-92-1 ]
[ 76410-58-7 ]
2-amino-3-(2',6'-dichloro-biphenyl-4-yl)-propionic acid [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 3803 - 3805

3
[ 76410-58-7 ]
[ 14985-44-5 ]
(S)-2-amino-3-{4-[6-amino-9-(2-deoxy-β-D-erythropentafuranosyl)purin-8-yl]phenyl}propanoic acid [ No CAS ]

Reference： [1]Synlett,2005,p. 3005 - 3007
[2]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284
[3]Chemistry - A European Journal,2007,vol. 13,p. 6196 - 6203

4
[ 76410-58-7 ]
[ 2946-39-6 ]
(S)-2-amino-3-{4-[6-amino-9-(β-D-ribofuranosyl)purin-8-yl]phenyl}propanoic acid [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284
[2]Synlett,2005,p. 3005 - 3007

5
[ 862854-56-6 ]
[ 76410-58-7 ]
[ 898261-82-0 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

6
[ 76410-58-7 ]
[ 4659-45-4 ]
[ 863228-94-8 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 17; (S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-difluoromethoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid, Cpd 112; Compound 1e (1.47 mL, 10.2 mmol) was added to a mixture of Compound 1a (<strong>[76410-58-7]4-borono-L-phenylalanine</strong>) (2.04 g, 9.76 mmol) and Na2CO3 (2.07 g, 19.5 mmol) in acetonitrile:water (1:1, 40 mL) at 50 C. The resulting mixture was stirred at 50 C. for 1 h, then was cooled to 0 C. and was acidified to pH 2 by addition of concentrated HCl (aq). The suspension was stirred at 0 C. for 30 min and the precipitated solid was collected by vacuum filtration and was washed with water. The white solid was dried in a vacuum oven at 50 C., affording Compound 17a (2.65 g). 1H NMR (CD3OD) delta 7.55 (d, 2H, J=7.6 Hz), 7.28-7.40 (m, 5H), 4.95 (dd, 1H, J=9.3, 4.7 Hz), 3.30 (dd, 1H, J=13.9, 5.3 Hz), 3.03 (dd, 1H, J=14.1, 9.4 Hz).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1331 - 1335
[3]Patent: US2005/192279,2005,A1 .Location in patent: Page/Page column 38-39
[4]ChemMedChem,2019,vol. 14,p. 1315 - 1320

7
[ 76410-58-7 ]
[ 14628-57-0 ]
[ 862854-58-8 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1331 - 1335

8
[ 2004-06-0 ]
[ 76410-58-7 ]
(S)-3-{4-[9-(β-D-ribofuranosyl)purin-6-yl]phenyl}-2-aminopropanoic acid [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

9
[ 4594-45-0 ]
[ 76410-58-7 ]
(S)-3-{4-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]phenyl}-2-aminopropanoic acid [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

10
[ 76410-58-7 ]
[ 87-42-3 ]
(S)-3-{4-[9H-purin-6-yl]phenyl}-2-aminopropanoic acid [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

11
[ 76410-58-7 ]
[ 23567-96-6 ]
(S)-2-amino-3-{4-[6-amino-9-(β-D-ribofuranosyl)purin-8-yl]phenyl}propanoic acid 5'-O-phosphate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

12
8-bromo-2'-deoxy-adenosine 5'-monophosphate triethylammonium salt [ No CAS ]
[ 76410-58-7 ]
(S)-2-amino-3-{4-[6-amino-9-(2'-deoxy-β-D-erythropentafuranosyl)purin-8-yl]phenyl}propanoic acid 5'-O-phosphate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

13
[ 66695-81-6 ]
[ 76410-58-7 ]
(S)-2-amino-3-{4-[6-amino-9-(β-D-ribofuranosyl)purin-8-yl]phenyl}propanoic acid 5'-O-triphosphate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

14
C₁₀H₁₅BrN₅O₁₂P₃*C₆H₁₅N [ No CAS ]
[ 76410-58-7 ]
(S)-2-amino-3-{4-[6-amino-9-(2'-deoxy-β-D-erythropentafuranosyl)purin-8-yl]phenyl}propanoic acid 5'-O-triphosphate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

15
[ 54-42-2 ]
[ 76410-58-7 ]
(S)-2-amino-3-{4-[1-(2-deoxy-β-D-erythro-pentofuranosyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl}propanoic acid [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 6196 - 6203

16
[ 76410-58-7 ]
[ 92410-99-6 ]
(S)-2-amino-3-{4-[6-amino-9-(2'-deoxy-β-D-erythropentafuranosyl)purin-8-yl]phenyl}propanoic acid 5'-O-triphosphate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 6196 - 6203

17
[ 76410-58-7 ]
[ 3731-55-3 ]
(S)-2-amino-3-{4-[1-(2-deoxy-β-D-erythro-pentofuranosyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl}propanoic acid 5'-O-triphosphate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 6196 - 6203

18
[ 214833-26-8 ]
[ 76410-58-7 ]
(S)-2-amino-3-{4-[6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-7-deazapurin-7-yl]phenyl}propanoic acid 5'-O-triphosphate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 6196 - 6203

19
[ 76410-58-7 ]
[ 166247-63-8 ]
(S)-2-amino-3-{4-[6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-7-deazapurin-7-yl]phenyl}propanoic acid [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 6196 - 6203

20
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-methoxy-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

21
[ 76410-58-7 ]
[ 863226-76-0 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

22
[ 76410-58-7 ]
(S)-3-[4-(5-Amino-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-2-(2,6-dichloro-benzoylamino)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

23
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-hydroxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

24
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

25
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-ethoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

26
[ 76410-58-7 ]
3-[4-(2-<i>tert</i>-butyl-5-methoxy-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-2-(2,6-dichloro-benzoylamino)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

27
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-difluoromethoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

28
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-{4-[5-(2-hydroxy-ethoxy)-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl]-phenyl}-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

29
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(5-methoxy-3-oxo-2-phenyl-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

30
[ 76410-58-7 ]
2-(2,6-dichloro-benzoylamino)-3-[4-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid 2-hydroxy-ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

31
[ 76410-58-7 ]
[ 863226-74-8 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

32
[ 76410-58-7 ]
(S)-3-[4-(2-Benzyl-5-methoxy-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-2-(2,6-dichloro-benzoylamino)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

33
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(2-methyl-5-morpholin-4-yl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

34
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-[4-(2-methyl-3-oxo-5-pyrrolidin-1-yl-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

35
[ 76410-58-7 ]
(S)-3-[4-(2-Cyclohexyl-5-methoxy-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-2-(2,6-dichloro-benzoylamino)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

36
[ 76410-58-7 ]
(S)-3-[4-(5-Cyclohexyloxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-2-(2,6-dichloro-benzoylamino)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

37
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-{4-[2-methyl-5-(2-morpholin-4-yl-ethoxy)-3-oxo-2,3-dihydro-pyridazin-4-yl]-phenyl}-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

38
[ 76410-58-7 ]
(S)-2-(2,6-Dichloro-benzoylamino)-3-{4-[5-methoxy-2-(2-morpholin-4-yl-ethyl)-3-oxo-2,3-dihydro-pyridazin-4-yl]-phenyl}-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3402 - 3411

39
[ 76410-58-7 ]
[ 412024-58-9 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 983 - 985

40
[ 76410-58-7 ]
[ 224824-22-0 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 983 - 985
[2]Angewandte Chemie - International Edition,2014,vol. 53,p. 11046 - 11050
Angew. Chem.,2014,vol. 126,p. 11226 - 11230,5

41
[ 76410-58-7 ]
4-amidino-L-phenylalanine, methyl ester, bis-trifluoroacetate [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 983 - 985

42
[ 5513-40-6 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

43
[ 183070-41-9 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

44
[ 262604-00-2 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

45
[ 286472-74-0 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

46
[ 257628-00-5 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

47
[ 262604-03-5 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

48
[ 262603-99-6 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235
[2]Patent: WO2019/163738,2019,A1

49
[ 866114-96-7 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

50
[ 214491-30-2 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

51
[ 262604-02-4 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

52
[ 262603-98-5 ]
[ 76410-58-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 231 - 235

53
[ 76410-58-7 ]
[ 2073-59-8 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

54
[ 76410-58-7 ]
[ 3249-01-2 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

55
[ 76410-58-7 ]
[ 3561-36-2 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

56
[ 76410-58-7 ]
[ 3956-78-3 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

57
[ 76410-58-7 ]
[ 77374-27-7 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

58
[ 76410-58-7 ]
[ 77374-26-6 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

59
[ 76410-58-7 ]
[ 77374-28-8 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3435 - 3438

60
[ 1928-76-3 ]
[ 76410-58-7 ]
(S)-2-amino-3-[4-(9-benzylpurin-6-yl)phenyl]propionic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		DIOXANE/WATER (2: 1,5 ml) was added through septum to an argon purged flask containing 9-benzyl-6-chloropurine (59 mg, 0.24 MMOL), (S) -4-boronophenylalanine (63 MG, 0.3 MMOL), K2CO3 (88 mg, 0.64 mmol) and PD (PPH3) 4 (23 mg, 0.02 MMOL). The mixture was stirred at 90C for 4 hr, diluted with water (40 ml) and pH of the solution was adjusted with aqueous HC1 (2%) to 4. The mixture was washed with ethyl acetate and the solvent was evaporated in vacuo from the water part. The solid residue was dissolved in water (1.5 ml) and crystallized from the solution at room temperature DURING 48 hr to give the title compound (50 mg, yield 61%) as white crystals. 1H NMR (400 MHz, DMSO-d6) : 3.15 (dd, 1H, J = 7.0 and 14.1, CHAHBCH) ; 3. 26 (dd, 1H, J = 5. 4 and 14.1, CHAHBCH) ; 3. 95 (t, 1H, J = 6.1 ; CHCH2) ; 5. 54 (s, 2H, CH2Ph) ; 7.30-7. 40 (m, 5H, AROM.) ; 7.50 (d, 2H, J 8. 2, arom. ) ; 8.75 (d, 2H, J = 8.2, arom. ); 8.82 (s, 1H, H-8); 8.96 (s, 1H, H-2). 3C NMR (100.6 MHz, DMSO-d6) : 35.75 (CHZCH) ; 46. 48 (CH2PH) 53.18 (CHCH2) ; 127. 67, 127.90, 128.71, 129.46 and 139.80 (5 x CH-AROM. ); 130.19 (C-5); 134.23 (C-AROM. ) ; 136. 42 (C-AROM. ) ; 138.45 (C-arom. ); 146.44 (CH-8); 151.94 (CH-2); 152.26 and 152. 46 (C-4 and C-6) ; 170.16 (CO).

Reference： [1]Patent: WO2004/94426,2004,A1 .Location in patent: Page 44

Yield	Reaction Conditions	Operation in experiment
		That is, the arylborate 5b (0.38 g, 0.59 mmol) was dissolved in a mixed solvent of ethyl acetate (5 ml), chloroform (5 ml) and methanol (5 ml), and after adding palladium hydroxide (0.10 g), one drop of acetic acid was added to effect hydrogen substitution and the mixture was stirred at 40 C. for 24 hours. Palladium catalyst was removed by filtration through celite. To the reaction mixture was added 1 ml of water, the solvent was removed washed with methylene chloride to give L-p-boronophenylalanine (0.09 g, yield: 74%).

62
[ 76410-58-7 ]
[ 186792-13-2 ]
[ 862854-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; for 96h;Heating / reflux;	Procedure 8; 4-Borono-L-phenylalanine (0.30 g, 1.0 mmol), 4-Bromo-5-methoxy-2- methyl-2H-pyridazin-3-one (0.35 g, 1.0 mmol), tetrakistriphenylphosphine palladium(O) (0.09 g), and 2.0 M aqueous sodium carbonate (3.0 ml_) were refluxed in MeCN (900 ml_) for 4 d. The mixture was acidified with 2.0 N HCI and treated with MeOH. The solid was filtered off and the mixture was concentrated in vacuo. The crude solid was purified using a Gilson HPLC containing a Kromasil column (10u, 1OthetaA C18, column length 250x50 mm, gradient 100:0 to 10:90 H2O:MeCN) to give 2-(S)-Amino-3-[4-(5-methoxy-2- methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-propionic acid. MS (ES+) 304.

Reference： [1]Patent: WO2006/52962,2006,A2 .Location in patent: Page/Page column 46

63
[ 87-99-0 ]
[ 76410-58-7 ]
L-p-boronophenylalanine-xylitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		L-p-Boronophenylalanine-polyol or -aminopolyol complexes are prepared by combining 0.5 mM of alpha-deuterated or alpha-hydrogenated L-p-BPA with between 1.00 and 1.05 equivalents of complexing agent (with the exception of poorly complexing polyols and carbohydrates, in which up to 4.3 equivalents of polyol or carbohydrates are used) in 2 mL of water. One equivalent of NaOH (1 mL of 0.5 M) is then added and the slurry gently warmed if needed in order to dissolve all solids. The pH is then monitored and reduced to between 7.5 and 7.3 by the addition of Dowex50WX4-50 ion exchange resin. The clear solution is then passed through a 0.2 mum syringe filter and then freeze-dried to constant weight. 1H and 13C NMR spectra are recorded on a GE 300 MHz FT-NMR spectrometer with D2O buffered at 7.4 [Bates, R G, Bower, V E. 1956. Alkaline solutions for pH control. Anal. Chem. 28:1322-1324] as the solvent. The binding constants are calculated at three different concentrations by integration of the free L-p-BPA aromatic protons (7.73 and 7.33 ppm) compared with those of the L-p-BPA complexes (7.5 and 7.2 ppm). Spectra of the 1:1 complexes are reported. L-p-boronophenylalanine-xylitol complex 1H NMR delta 7.52 (d, J=7.3 Hz, 2H), 7.20 (d, J=7.3 Hz, 2H), 3.95 (dd, J=8.1, 5.1 Hz, 1H), 3.25 and 3.02 (ABq, JAB=14.7 Hz, the peaks at 3.25 and 3.02 are further split into d with J=5.1 and 8.1, respectively, 2H); 13C NMR delta 177.0 (s), 146.0 (s), 135.8 (s), 135.1 (d, 2C), 130.9 (d, 2C), 77.8 (d), 74.6 (d), 73.4 (d), 66.0 (t), 65.3 (t), 58.8 (d), 39.0 (t).

Reference： [1]Patent: US2007/104648,2007,A1 .Location in patent: Page/Page column 14

64
[ 945978-21-2 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(2-(trifluoromethyl)phenyl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Tetrabutylammonium fluoride (0.1 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 2-trifluoromethyl-benzaldehyde (1.74 g, 10 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (1.8 ml, 12 mmol) in 10 ml THF at 0 C. The formed mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was then treated with 12 ml of 1N HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 2.2 g of 1-(2-trifluoromethylphenyl)-2,2,2-trifluoro-ethanol, yield 90%. NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 1-(2-trifluoromethylphenyl)-2,2,2-trifluoro-ethanol (244 mg, 1 mmol) in 10 ml of anhydrous THF. The mixture was stirred for 20 minutes, 2-amino-4,6-dichloro-pyrimidine (164 mg, 1 mmol) was added and then the reaction mixture was heated at 70 C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 267 mg of 4-chloro-6-[2,2,2-trifluoro-1-(2-trifluoromethylphenyl)-ethoxy]-pyrimidin-2-ylamine, yield 71%. In a microwave vial, 4-chloro-2-amino-6-[1-(2-trifluoromethylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidine (33 mg, 0.1 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol) and 1 ml of acetonitrile, 0.7 ml of water. 0.3 ml of 1N aqueous sodium carbonate was added to above solution followed by 5 mole percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150 C. for 5 minutes with microwave irradiation. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, and then was purified by Prep-LC to give 5.6 mg of 2-amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-trifluoromethylphenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid. 1H NMR (400 MHz, CD3OD) delta 7.96 (m, 3H), 7.80 (d, J=8.06 Hz, 1H), 7.74 (t, J=7.91 Hz 1H), 7.63 (t, J=8.06 Hz, 1H), 7.41 (d, J=8.3 Hz, 2H), 7.21 (m, 1H), 6.69 (s, 1H), 3.87 (m, 1H), 3.34 (m, 1H), 3.08 (m, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 23-24

65
[ 945978-22-3 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-p-tolylethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Tetrabutylammonium fluoride (0.1 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 4-methyl-benzaldehyde (1.2 g, 10 mmol) and TMSCF3 (1.8 ml, 12 mmol) in 10 ml THF at 0 C. The formed mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was then treated with 12 ml of 1N HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 1.6 g of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol, yield 86%. NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol (190 mg, 1 mmol) in 10 ml of anhydrous THF. The mixture was stirred for 20 minutes, 2-amino-4,6-dichloro-pyrimidine (164 mg, 1 mmol) was added and then the reaction mixture was heated at 70 C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 209 mg of 4-chloro-6-[1-(4-methylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine, yield 66%. A microwave vial was charged with 4-chloro-2-amino-6-[1-(4-methylphenyl)-2,2,2-trifluoro-ethoxy]-pyrimidine (33 mg, 0.1 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol) and 1 ml of acetonitrile, 0.7 ml of water. Aqueous sodium carbonate (0.3 ml, 1N) was added to above solution followed by 5 mol percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes with microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, was then purified by Prep-LC to give 14.6 mg of 2-amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(4-methylphenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid. 1H NMR (300 MHz, CD3OD) delta 7.94 (d, J=8.20 Hz, 2H), 7.47 (d, J=7.24 Hz, 4H), 7.27 (d, J=8.01 Hz, 2H) 6.80 (s, 1H), 6.75 (m, 1H), 4.30 (t, 1H), 3.21-3.44 (m, 2H), 2.37 (s, 3H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 24

66
[ 945978-23-4 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(2-amino-6-(1-cyclohexyl-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Cyclohexanecarbaldehyde (0.9 g, 5 mmol) was dissolved in 10 ml aqueous 1,4-dioxane, to which 200 mg (10 mmol) sodium borohydride was added. The reaction was run overnight at room temperature. After completion of the reaction, 5 ml 10% HCl solution was added and the product was extracted with ethyl acetate. The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 0.8 g of 1-cyclohexyl-2,2,2-trifluoro-ethanol, yield 88%. NaH (80 mg, 60%, 3.0 mmol) was added to the solution of 1-cyclohexyl-2,2,2-trifluoro-ethanol (182 mg, 1 mmol) in 10 ml of anhydrous THF, the mixture was stirred for 20 minutes, 2-amino-4,6-dichloro-pyrimidine (164 mg, 1 mmol) was added and then the reaction mixture was heated at 70 C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 202 mg of 4-chloro-6-[1-cyclohexyl-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine, yield 65%. In a microwave vial, 4-chloro-2-amino-6-[1-cyclohexane-2,2,2-trifluoro-ethoxy]-pyrimidine (33 mg, 0.1 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol) and 1 ml of acetonitrile, 0.7 ml of water, 0.3 ml of aqueous sodium carbonate (1M) was added to above solution followed by 5 mol percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes with a microwave. After cooling, the reaction mixture was evaporated to dryness, the residue was dissolved in 2.5 ml of methanol, and the product was purified by Prep-LC to give 4.9 mg 2-amino-3-{4-[2-amino-6-(1-cyclohexyl-2,2,2-trifluoro-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid. 1H NMR (300 MHz, CD3Cl) delta 7.95 (d, J=8.39 Hz, 2H), 7.49 (d, J=8.39 Hz, 2H), 6.72 (s, 1H), 5.90 (m, 1H), 4.33 (t, 1H), 3.21-3.44 (m, 2H), 1.73-2.00 (m, 6H), 1.23-1.39 (m, 5H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 24

67
[ 945978-24-5 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-(6-(2-fluorophenoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 2-fluorophenol (112 mg, 1 mmol) in 10 ml of anhydrous THF, the mixture was stirred for 20 minutes, 4,6-dichloro-pyrimidine (149 mg, 1 mmol) was added and then the reaction mixture was heated at 70 C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 146 mg of 4-chloro-6-(2-fluorophenoxy)-pyrimidine, yield 65%. A microwave vial (2 ml) was charged with 4-chloro-6-[2-fluorophenoxy]-pyrimidine, (33 mg, 0.1 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol) and 1 ml of actonitrile, 0.7 ml of water, 0.3 ml of aqueous sodium carbonate (1M) was added to above solution followed by 5 mol % of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness, the residue was dissolved in 2.5 ml of methanol, and the product was purified with Prep-LC to give 4.9 mg 2-amino-3-{4-[2-amino-6-(1-2-fluorophenyl-2,2,2-trifluoro-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid. 1H NMR (400 MHz, CD3OD) delta 8.74 (s, 1H), 8.17 (d, J=8.06 Hz, 2H), 7.63 (s, 1H), 7.50 (d, J=8.06 Hz, 2H), 7.30 (m, 5H), 4.33 (m, 1H), 3.34 (m, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 24-25

68
[ 945978-25-6 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(4-(3-(4-chlorophenyl)piperidin-1-yl)-1,3,5-triazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3-(4-Chlorophenyl)piperidine (232 mg, 1 mmol) was added to a solution of 2,4-dichlorotriazine (149.97 mg, 1 mmol), and 300 mg diisopropylethyl amine in 10 ml THF at 0 C. The formed mixture was warmed up to room temperature and stirred for 1 hour. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 328 mg of 2-chloro-4-[3-(4-chlorophenyl)-piperidin-1-yl]-[1,3,5]triazine. A microwave vial was charged with 2-chloro-4-[3-(4-chlorophenyl)-piperidin-1-yl]-[1,3,5]triazine (62 mg, 0.2 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (60 mg, 0.3 mmol), 1 ml of acetonitrile, and 0.7 ml of water. Aqueous sodium carbonate (0.6 ml; 1M) was added to the solution, followed by 5 mol percent dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes with microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, was then purified by Prep-LC to give 5.1 mg of 2-amino-3-(4-{4-[3-(4-chlorophenyl)-piperidin-1-yl]-[1,3,5]triazin-2-yl}-phenyl)-propionic acid. 1H NMR (400 MHz, CD3Cl) delta 8.58 (d, 2H), 8.05 (d, 2H), 7.47 (m, 5H), 4.96 (m, 1H), 4.23 (m, 2H), 3.21-3.44 (m, 4H), 2.37 (m, 5H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 25

69
[ 945978-26-7 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(4-amino-6-(2,2,2-trifluoro-1-phenylethoxy)-1,3,5-triazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 2,2,2-trifluoro-1-phenyl-ethanol (176 mg, 1 mmol) in 10 ml of anhydrous 1,4-dioxane. The mixture was stirred for 20 minutes, then added to a solution of 2-amino-4,6-dichloro-triazine (164 mg, 1 mmol) in 30 ml of 1,4-dioxane at 0 C. for 1 hour. The reaction mixture was then warmed to room temperature. After completion of the reaction, 5 ml of water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 198 mg of 4-chloro-6-[2,2,2-trifluoro-1-phenyl-ethoxy]-[1,3,5]triazine-2-ylamine, yield 65%. A microwave vial was charged with 4-chloro-6-[2,2,2-trifluoro-1-phenyl-ethoxy]-[1,3,5]triazine-2-ylamine (33 mg, 0.1 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol), 1 ml of actonitrile, and 0.7 ml of water. Aqueous sodium carbonate (0.3 ml, 1M) was added to above solution followed by 5 mol percent dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, was then purified with Prep-LC to give 3.2 mg 2-amino-3-{4-[4-amino-6-(1-phenyl-2,2,2-trifluoro-ethoxy]-[1,3,5]triazin-2-yl]-phenyl)-propionic acid. 1H NMR (300 MHz, CD3OD) delta 8.22 (d, J=8.20 Hz, 2H), 7.52 (m, 2H), 7.33 (m, 5H) 6.62 (m, 1H), 4.19 (t, 1H), 3.1-3.33 (m, 2H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 25

70
[ 945978-32-5 ]
[ 76410-58-7 ]
2-amino-3-[4'-(3-cyclophentyloxy-4-methoxy-benzylamino)-biphenyl-4-yl]-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%		Sodium triacetoxyl-borohydride (470 mg, 2.21 mmol) was added to a solution of 4-bromo-phenylamine (252 mg, 1.47 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (324 mg, 1.47 mmol) in 10 ml of 1,2-dicloroethtane (DCE), 0.5 ml of HOAc was added. The mixture was stirred overnight at room temperature, followed by addition of 15 ml of DCE. The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by rotovap to give 656 mg of crude (4-bromo-phenyl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine. It was used for next step without further purification. An Emrys process vial (2-5 ml) for microwave was charged with (4-bromo-phenyl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine (84 mg, 0.22 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (46 mg, 0.22 mmol) and 2 ml of acetonitrile. Aqueous sodium carbonate (2 ml, 1M) was added to above solution, followed by 5 mol percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol and purified with Prep-LC to give 5 mg of 2-amino-3-[4'-(3-cyclophentyloxy-4-methoxy-benzylamino)-biphenyl-4-yl]-propionic acid, yield 5%. 1H-NMR (400 MHz, DMSO-d6): delta 1.46 (m, 2H), 1.62 (m, 4H), 3.01 (m, 2H), 3.64 (s, 3H), 4.14 (s, 3H), 4.66 (m, 1H), 6.61 (d, 2H), 6.81 (s, 2H), 6.88 (s, 1H), 7.18 (d, 2H), 7.31 (d, 2H), 7.44 (d, 2H), 7.60 (m, 1H), 8.19 (s, 3H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 26
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3684 - 3687

71
[ 945978-33-6 ]
[ 76410-58-7 ]
(S)-2-Amino-3-(4-(6-(3-(cyclopentyloxy)-4-methoxybenzylamino)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%		Sodium tiracetoxyl-borohydride (985 mg, 4.65 mmol) was added to a solution of 6-chloro-pyrimidin-4-ylamine (200 mg, 1.55 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (682 mg, 3.1 mmol) in 25 ml of DCE. 1 ml of HOAc was added, and the mixture was stirred overnight at 50 C., followed by addition of 25 ml of DCE. The organic phase was washed with water, and the product was purified with column (silica gel, hexane:EtOAc 5:1) to give 64 mg of (6-chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine, yield 12%. An Emrys process vial (2-5 ml) for microwave was charged with (6-chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine (64 mg, 0.19 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (40 mg, 0.19 mmol) and 2 ml of acetonitrile. Aqueous sodium carbonate (2 ml, 1M) was added to above solution followed by 5 mol percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes with microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol and purified with Prep-LC to give 5.3 mg of 2-amino-3-{4-[6-(3-cyclopentyloxy-4-methoxy-benzylamino)-pyrimidin-4-yl]-phenyl}-propionic acid, yield 6%. 1H-NMR (400 MHz, DMSO-d6): delta 1.46 (m, 2H), 1.62 (m, 4H), 3.01 (m, 2H), 3.08 (m, 2H), 3.65 (s, 3H), 4.20 (m, 1H), 4.46 (d, 2H), 4.68 (m, 1H), 6.82 (t, 2H), 6.87 (d, 2H), 7.40 (d, 2H), 7.90 (s, 2H), 8.25 (s, 2H), 8.6 (s, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 27

72
[ 945978-34-7 ]
[ 76410-58-7 ]
(S)-2-Amino-3-(4-(6-(3-(cyclopentyloxy)-4-methoxybenzylamino)pyrazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%		Sodium triacetoxyl-borohydride (1315 mg, 6.2 mmol) was added to a solution of 6-chloro-pyrazin-2-yl-amine (400 mg, 3.10 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (818 mg, 3.7 mmol) in 50 ml of DCE, 1 ml of HOAc was added and the mixture was stirred overnight at 50 C., followed by addition of another 50 ml of DCE. The organic phase was washed with water, and the product was purified with column (silica gel, hexane:EtOAc 6:1) to give 50 mg of (6-chloro-pyrazin-2-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine, yield 10%. An Emrys process vial (2-5 ml) for microwave was charged with (6-chloro-pyrazin-2-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine (50 mg, 0.15 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol) and 2 ml of acetonitrile. Aqueous sodium carbonate (2 ml, 1M) was added to the solution followed by 5 mol percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, and the product was purified with Prep-LC to give 5.5 mg of 2-amino-3-{4-[6-(3-cyclopentyloxy-4-methoxy-benzylamino)-pyrazin-2-yl]-phenyl}-propionic acid, yield 6%. 1H-NMR (400 MHz, DMSO-d6): delta 1.46 (m, 2H), 1.62 (m, 4H), 3.01 (m, 2H), 3.08 (m, 2H), 3.65 (s, 3H), 4.0 (m, 1H), 4.45 (d, 2H), 4.65 (m, 1H), 6.90 (s, 2H), 6.95 (s, 1H), 7.32 (d, 2H), 7.60 (t, 1H), 7.90 (s, 1H), 7.95 (d, 2H), 8.25 (s, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 27

73
[ 945978-35-8 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-(5-((4'-methylbiphenyl-2-yl)methylamino)pyrazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		Sodium tiracetoxyl borohydride (215 mg, 1.02 mmol) was added to the solution of 4'-methyl-biphenyl-2-carbaldehyde and 5-bromo-pyrazin-2-ylamine in 5 ml of DCE, 0.1 ml of HOAc was added and the mixture was stirred overnight at room temperature, followed by addition of 5 ml of DCE. The organic phase was washed with water, and purified with column (silica gel, hexane:EtOAc 6:1) to give 100 mg of (5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine, yield 55%. An Emrys process vial (2-5 ml) for microwave was charged with (5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine (25 mg, 0.071 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (22 mg, 0.11 mmol) and 1 ml of acetonitrile. Aqueous sodium carbonate (1 ml, 1M) was added to the solution followed by 5 mol percent dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, and the product was purified with Prep-LC to give 19 mg of 2-amino-3-{4-[6-(3-cyclopentyloxy-4-methoxy-benzylamino)-pyrazin-2-yl]-phenyl}-propionic acid, yield 63%. 1H-NMR (400 MHz, CD3OD): delta 2.22 (s, 3H), 3.09 (m, 1H), 3.25 (m, 1H), 4.18 (t, 1H), 4.40 (s, 2H), 7.07 (d, 2H), 7.14 (m, 3H), 7.24 (m, 4H), 7.36 (m, 1H), 7.72 (d, 2H), 7.84 (s, 1H), 8.20 (d, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 27-28

74
[ 945978-36-9 ]
[ 76410-58-7 ]
(2S)-2-Amino-3-(4-(6-(2,2,2-trifluoro-1-phenylethoxy)-pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%		NaH (60%, 120 mg, 3.0 mmol) was added to a solution of 2,2,2-trifluoro-1-phenyl-ethanol (350 mg, 2.03 mmol) in 5 ml of THF. The mixture was stirred for 20 minutes at room temperature. 4,6-Dichloro-pyrimidine (300 mg, 2.03 mmol) was added and then the reaction mixture was heated at 70 C. for 1 hour. After cooling, the THF was evaporated to provide a residue, which was dissolved in 15 ml of EtOAc, and then washed with water, and dried over sodium sulfate. The solvent was removed by rotovap to give 550 mg of 4-chloro-6-(2,2,2-trifluoro-1-phenyl-ethoxy)-pyrimidine, yield 95%. An Emrys process vial (2-5 ml) for microwave was charged with 4-chloro-6-(2,2,2-trifluoro-1-phenyl-ethoxy)-pyrimidine (30 mg, 0.11 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (32 mg, 0.16 mmol), 1 ml of acetonitrile and 0.6 ml of water. Aqueous sodium carbonate (0.42 ml, 1M) was added to above solution followed by 10 mol percent of POPd2 (dihydrogen di-mu-chlorodichlorobis(di-tert-butylphosphinito-kappaP) dipalladate. The reaction vessel was sealed and heated to 120 C. for 30 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, and the product was purified with Prep-LC to give 4.8 mg of 2-amino-3-{4-[6-(2,2,2-trifluoro-1phenyl-ethoxy)-pyrimidin-4-yl]-phenyl}-propionic acid, yield 11%. 1H-NMR (400 MHz, CD3OD): delta 3.20 (m, 1H), 3.40 (m, 1H), 4.25 (t, 1H), 6.82 (dd, 1H), 7.43 (m, 5H), 7.57 (s, 1H), 7.60 (m, 2H), 8.10 (d, 2H), 8.75 (s, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 28

75
[ 945978-38-1 ]
[ 76410-58-7 ]
(2S)-2-Amino-3-(4-(6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		Tetrabutylammonium fluoride (TBAF: 0.1 ml, 1M) in THF was added to a solution of 3,4-difluro-benzaldehyde (1.42 g, 10 mmol) and (trifluromethyl)trimethylsilane (1.70 g, 12 mmol) in 10 ml THF at 0 C. The mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was treated with 12 ml of 1M HCl and stirred overnight. The product was extracted with dicloromethane (3×20 ml), the organic layer was combined and passed through a pad of silica gel. The organic solvent was evaporated to give 1.9 g of 1-(3,4-difluoro-phenyl)-2,2,2-trifluoro-ethanol, yield 90%. NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 1-(3,4-Difluoro-phenyl)-2,2,2-trifluoro-ethanol (212 mg, 1 mmol) in 5 ml of THF, the mixture was stirred for 20 minutes at room temperature. 4,6-Dichloro-pyrimidine (149 mg, 1 mmol) was added and then the reaction mixture was heated at 70 C. for 1 hour. After cooling, THF was evaporated. The residue was dissolved in 15 ml of EtOAc, and then washed with water, dried over sodium sulfate. The solvent was removed by rotovap to give 230 mg of 4-chloro-6-[1-(3,4-difluoro-phenyl)-2,2,2-trifluoro-ethoxy]-pyrimidine, yield 70%. An Emrys process vial (2-5 ml) for microwave was charged with 4-chloro-6-[1-(3,4-difluoro-phenyl)-2,2,2-trifluoro-ethoxy]-pyrimidine (33 mg, 0.1 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (31 mg, 0.15 mmol), 1 ml of acetonitrile and 0.7 ml of water. Aqueous sodium carbonate (0.3 ml, 1M) was added to above solution followed by 5 mol % of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150 C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, then purified with Prep-LC to give 10 mg of 2-amino-3-(4-{6-[1-(3,4-difluoro-phenyl)-2,2,2-trifluoro-ethoxy]-pyridin-4-yl}-phenyl)-propionic acid, yield 21%. 1H-NMR (400 MHz, CD3OD): delta 3.11 (m, 1H), 3.27 (m, 1H), 4.19 (dd, 1H), 6.78 (q, 1H), 7.26 (m, 2H), 7.35 (d, 3H), 7.49 (m, 2H), 8.02 (d, 2H), 8.66 (s, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 28

76
[ 945978-61-0 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-{5-[(biphenyl-4-ylmethyl)-amino]-pyrazin-2-yl}-phenyl)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4-Phenylbenzaldehyde (0.3 g, 1.65 mmol) and 2-amino-5-bromopyrazine (0.24 g, 1.37 mmol) were treated with Na(OAc)3BH (0.44 g, 2.06 mmol) in dichloroethane (7.0 mls) and acetic acid (0.25 mls) for 18 hours at room temperature. The mixture was diluted with dichloromethane, washed with 1.0 N NaOH, washed with brine, dried over MgSO4, and concentrated. Chromatography (SiO2, EtOAc:Hex, 1:1) gave 0.18 g of N-(biphenyl-4-ylmethyl)-5-bromopyrazin-2-amine. N-(biphenyl-4-ylmethyl)-5-bromopyrazin-2-amine (60 mg, 0.176 mmol), L-p-boronophenylalanine (37 mg, 0.176 mmol), palladiumtriphenylphosphine dichloride (3.6 mg, 0.0052 mmol), Na2CO3 (37 mg, 0.353 mmol), acetonitrile (1.25 mls) and water (1.25 mls) were heated in a microwave reactor at 150 C. for 5 minutes. The mixture was concentrated, dissolved in 1.0 N HCl, washed twice with ether, concentrated and purified by preprative HPLC to give 41 mgs of the title compound. M+1=425; 1H NMR (CD3OD) delta 8.42 (s, 1H), 8.05 (s, 1H), 7.92 (d, 2H), 7.58 (d, 4H), 7.40 (m, 7H), 4.60 (s, 2H), 4.25 (m, 1H), 3.40 (m, 1H), 3.20 (m , 1H).

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3684 - 3687
[2]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 34

77
[ 945978-62-1 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-(5-(naphthalen-2-ylmethylamino)pyrazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2-Napthaldehyde (0.6 g, 3.84 mmol) and 2-amino-5-bromopyrazine (0.56 g, 3.201 mmol) were treated with Na(OAc)3BH (1.02 g, 4.802 mmol) in dichloroethane (15.0 mls) and acetic acid (0.5 mls) for 18 hours at room temperature. The mixture was diluted with dichloromethane, washed with 1.0 N NaOH, washed with brine, dried over MgSO4, and concentrated. Chromatography (SiO2, EtOAc:Hex, 1:1) gave 0.49 g 5-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine. 5-Bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine (0.2 g, 0.637 mmol), L-p-boronophenylalanine (0.13 g, 0.637 mmol), palladiumtriphenylphosphine dichloride (13 mg, 0.019 mmol), Na2CO3 (0.13 g, 1.27 mmol), acetonitrile (5 mls) and water (5 mls) were heated in a microwave reactor at 150 C. for 5 minutes. The mixture was concentrated, dissolved in 1.0 N HCl, washed twice with ether, concentrated, dissolved in methanol, filtered and concentrated to yield 0.12 g of the captioned compound. M+1=399; 1H NMR (CD3OD) delta 8.51 (s, 1H), 8.37 (s, 1H), 7.90 (m, 6H), 7.50 (m, 5H), 4.85 (s, 2H), 4.30 (t, 1H), 3.38 (m, 1H), 3.22 (m, 1H).

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3684 - 3687
[2]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 34

78
[ 945978-64-3 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		To 4'-bromo-2,2,2-trifluoroacetophenone (5.0 g, 19.76 mmol) in THF (50 mls) at 0 C. was added NaBH4 (1.5 g, 39.52 mmol). The mixture was warmed to room temperature and stirred for 1 hour. The reaction was complete by TLC (CH2Cl2). The mixture was quenched with H2O, rotary evaporated to remove most of the THF, and extracted 2 times with CH2Cl2. The organics were combined, washed with brine, concentrated to a small volume and filtered through a plug of silica gel. The silica was washed with CH2Cl2 to elute the product, and the resulting solution was concentrated to give 4.65 g of 1-(4-bromophenyl)-2,2,2-trifluoroethanol. Yield 92%. To Pd(PPh3)4 (2.1 g, 1.823 mmol) was added 3-fluorophenylmagnesium bromide (55 mls, 1.0 M in THF, 55 mmol) at 0 C. over 15 minutes. The ice bath was removed and the mixture was stirred for 30 minutes. 1-(4-Bromophenyl)-2,2,2-trifluoroethanol (4.65 g, 18.23 mmol) in THF (50 mls) was added over 10 minutes. The mixture was heated to reflux for 3 hours and was shown complete by LC (Sunfire column, TFA). The mixture was cooled, quenched with H2O, rotary evaporated to remove most of the THF, and extracted 3 times with CH2Cl2. The organics were combined washed with brine, dried over MgSO4, and concentrated. Chromatography (SiO2, CH2Cl2) gave 4.64 g of 2,2,2-trifluoro-1-(3'-fluorobiphenyl-4-yl)ethanol. Yield 94%. To 2,2,2-trifluoro-1-(3'-fluorobiphenyl-4-yl)ethanol (1.4 g, 5.18 mmol) in THF (50 mls) at 0 C. was added NaH (60% in mineral oil, 0.31 g, 7.77 mmol). The ice bath was removed and the mixture was stirred for 30 minutes. 2-Amino-4,6-dichloropyrimidine (1.0 g, 6.22 mmol) in THF (25 mls) was added at once. The mixture was heated to 50 C. for 5 hours. The reaction was complete by LCMS (Sunfire, TFA). The mixture was cooled, quenched with brine, and extracted 3 times with CH2Cl2. The organics were combined, washed with brine, dried over MgSO4, and concentrated. Chromatography (SiO2, CH2Cl2) afforded 1.48 g of 4-chloro-6-(2,2,2-trifluoro-1-(3'-fluorobiphenyl-4-yl)ethoxy)pyrimidin-2-amine. Yield 73%. 4-Chloro-6-(2,2,2-trifluoro-1-(3'-fluorobiphenyl-4-yl)ethoxy)pyrimidin-2-amine (0.75 g, 1.89 mmol), L-p-boronophenylalanine (0.47 g, 2.26 mmol), Pd(PPh3)2Cl2 (79 mgs, 0.113 mmol), Na2CO3 (0.44 g, 4.15 mmol), acetonitrile (10 mls), and H2O (10 mls) were combined in a 20 ml microwave reactor and heated in the microwave at 150 C. for 7 minutes. The reaction was complete by LCMS (Sunfire, neutral). The mixture was concentrated, dissolved in NaOH (20 mls 0.5 N), filtered, extracted with ether three times, and cooled to 0 C. At 0 C., 1.0 N HCl was added slowly until a pH of 6.5 was attained. The mixture was stirred at 0 C. for 30 minutes and the product was filtered, dried in air, treated with excess 2.0 N HCl in ether, concentrated, then triturated with CH2Cl2 to give 1.12 g, 99% (95.5% purity). 385 mgs were purified via prep HPLC (Sunfire, TFA), concentrated, treated with excess 1.0 N HCl (aq.), concentrated to a small volume and lyophilized to afford 240 mgs of the captioned compound. M+1=527; 1H NMR delta (CD3OD) 7.86 (d, 2H), 7.64 (s, 4H), 7.49 (d, 2H), 7.36 (m, 2H), 7.28 (m , 1H), 7.02 (m, 1H), 6.95 (s, 1H), 6.75 (q, 1H), 4.26 (t, 1H), 3.32 (m, 1H), 3.21 (m, 1H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 35-36
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3684 - 3687

79
[ 76410-58-7 ]
[ 478258-60-5 ]
(S)-2-amino-3-(4-(2-amino-6-(benzylthio)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;Pd(PPh3)2Cl2; In water; acetonitrile;	4-(Benzylthio)-6-chloropyrimidin-2-amine (0.1 g, 0.397 mmol), L-p-boronophenylalanine (0.1 g, 0.477 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), Na2CO3 (93 mg, 0.874 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 0.42 g of the title compound. M+1=381; 1H NMR (CD3OD) delta 7.8 (d, 2H), 7.37 (t, 4H), 7.23 (m, 2H), 7.16 (m, 1H), 6.98 (s, 1H), 4.43 (s, 2H), 4.20 (t, 1H), 3.29 (m, 1H), 3.13 (M, 1H).
		Benzylmercaptan (0.14 g, 1.11 mmol) was treated with NaH (60% in mineral oil, 67 mg, 1.66 mmol) in dry THF (15 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (0.2 g, 1.22 mmol) was added and the mixture was stirred overnight. The mixture was diluted with methylenechloride, washed with water, then brine, dried over MgSO4, and concentrated to give 0.11 g of 4-(benzylthio)-6-chloropyrimidin-2-amine. 4-(Benzylthio)-6-chloropyrimidin-2-amine (0.1 g, 0.397 mmol), L-p-boronophenylalanine (0.1 g, 0.477 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), Na2CO3 (93 mg, 0.874 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 0.42 g of the title compound. M+1=381; 1H NMR (CD3OD) delta 7.8 (d, 2H), 7.37 (t, 4H), 7.23 (m, 2H), 7.16 (m, 1H), 6.98 (s, 1H), 4.43 (s, 2H), 4.20 (t, 1H), 3.29 (m, 1H), 3.13 (M, 1H).

Reference： [1]Patent: US2009/5382,2009,A1
[2]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 36

80
[ 945978-65-4 ]
[ 76410-58-7 ]
(S)-2-Amino-3-(4-(2-amino-6-(naphthalen-2-ylmethylthio)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; sodium carbonate;Pd(PPh3)2Cl2; In tetrahydrofuran; water; acetonitrile; mineral oil;	6.40. Synthesis of (S)-2-Amino-3-(4-(2-amino-6-(naphthalen-2-ylmethylthio)pyrimidin-4-yl)phenyl)propanoic acid 2-Mercaptonapthalene (0.2 g, 1. 148) was treated with NaH (60% in Mineral oil, 92 mg, 2.30 mmol) in dry THF (10 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (0.21 g, 1.26 mmol) was added and the mixture was stirred overnight. The mixture was diluted with methylenechloride, washed with water, then brine, dried over MgSO4, and concentrated to give 0.18 g 4-chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine. 4-Chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine (0.1 g, 0.331 mmol), L-p-boronophenylalanine (83 mg, 0.397 mmol), Pd(PPh3)2Cl2 (14 mg, 0.020 mmol), Na2CO3 (77 mg, 0.729 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 57 mg of the title compound. M+1=43 1; 1H NMR (CD3OD) delta 7.85 (s, 1H), 7.79 (d, 2H), 7.72 (d, 3H), 7.46 (dd, 1H), 7.35 (m, 4H), 6.95 (s, 1H), 4.58 (s, 2H), 4.17 (m, 1H), 3.26 (m, 1H), 3.11 (m, 1H).
	With NaH; sodium carbonate;Pd(PPh3)2Cl2; In tetrahydrofuran; water; acetonitrile; mineral oil;	6.40. Synthesis of (S)-2-Amino-3-(4-(2-amino-6-(naphthalen-2-ylmethylthio)pyrimidin-4-yl)phenyl)propanoic acid 2-Mercaptonapthalene (0.2 g, 1.148) was treated with NaH (60% in Mineral oil, 92 mg, 2.30 mmol) in dry THF (10 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (0.21 g, 1.26 mmol) was added and the mixture was stirred overnight. The mixture was diluted with methylenechloride, washed with water, then brine, dried over MgSO4, and concentratred to give 0.18 g 4-chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine. 4-Chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine (0.1 g, 0.331 mmol), L-p-boronophenylalanine (83 mg, 0.397 mmol), Pd(PPh3)2Cl2 (14 mg, 0.020 mmol), Na2CO3 (77 mg, 0.729 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 57 mg of the title compound. M+1=431; 1H NMR (CD3OD) delta 7.85 (s, 1H), 7.79 (d, 2H), 7.72 (d, 3H), 7.46 (dd, 1H), 7.35 (m, 4H), 6.95 (s, 1H), 4.58 (s, 2H), 4.17 (m, 1H), 3.26 (m, 1H), 3.11 (m, 1H).
	With NaH; sodium carbonate;Pd(PPh3)2Cl2; In tetrahydrofuran; water; acetonitrile; mineral oil;	6.38. Synthesis of (S)-2-Amino-3-(4-(2-amino-6-(naphthalen-2-ylmethylthio)pyrimidin-4-yl)phenyl)propanoic acid 2-Mercaptonapthalene (0.2 g, 1.148) was treated with NaH (60% in Mineral oil, 92 mg, 2.30 mmol) in dry THF (10 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (0.21 g, 1.26 mmol) was added and the mixture was stirred overnight. The mixture was diluted with methylenechloride, washed with water, then brine, dried over MgSO4, and concentrated to give 0.18 g 4-chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine. 4-Chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine (0.1 g, 0.331 mmol), L-p-boronophenylalanine (83 mg, 0.397 mmol), Pd(PPh3)2Cl2 (14 mg, 0.020 mmol), Na2CO3 (77 mg, 0.729 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 57 mg of the title compound. M+1=431; 1H NMR (CD3OD) delta 7.85 (s, 1H), 7.79 (d, 2H), 7.72 (d, 3H), 7.46 (dd, 1H), 7.35 (m, 4H), 6.95 (s, 1H), 4.58 (s, 2H), 4.17 (m, 1H), 3.26 (m, 1H), 3.11 (m, 1H).

2-Mercaptonapthalene (0.2 g, 1.148) was treated with NaH (60% in Mineral oil, 92 mg, 2.30 mmol) in dry THF (10 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (0.21 g, 1.26 mmol) was added and the mixture was stirred overnight. The mixture was diluted with methylenechloride, washed with water, then brine, dried over MgSO4, and concentratred to give 0.18 g 4-chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine. 4-Chloro-6-(naphthalen-2-ylmethylthio)pyrimidin-2-amine (0.1 g, 0.331 mmol), L-p-boronophenylalanine (83 mg, 0.397 mmol), Pd(PPh3)2Cl2 (14 mg, 0.020 mmol), Na2CO3 (77 mg, 0.729 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 57 mg of the title compound. M+1=431; 1H NMR (CD3OD) delta 7.85 (s, 1H), 7.79 (d, 2H), 7.72 (d, 3H), 7.46 (dd, 1H), 7.35 (m, 4H), 6.95 (s, 1H), 4.58 (s, 2H), 4.17 (m, 1H), 3.26 (m, 1H), 3.11 (m, 1H).

Reference： [1]Patent: US2009/5381,2009,A1
[2]Patent: US2009/5382,2009,A1
[3]Patent: US2009/29993,2009,A1
[4]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 36

81
[ 945978-66-5 ]
[ 76410-58-7 ]
(2S)-2-Amino-3-(4-(2-amino-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;Pd(PPh3)2Cl2; In water; acetonitrile;	4-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine (0.14 g, 0.421 mmol), L-p-boronophenylalanine (110 mg, 0.505 mmol), Pd(PPh3)2Cl2 (18 mg, 0.025 mmol), Na2CO3 (98 mg, 0.926 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 74 mg of the title compound. M+1=469; 1H NMR (CD3OD) delta 7.83 (d, 2H), 7.47 (m, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 4.21 (t, 1H), 3.29 (m, 1H), 3.15 (m, 1H).
	With sodium carbonate;Pd(PPh3)2Cl2; In water; acetonitrile;	4-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine (0.14 g, 0.421 mmol), L-p-boronophenylalanine (110 mg, 0.505 mmol), Pd(PPh3)2Cl2 (18 mg, 0.025 mmol), Na2CO3 (98 mg, 0.926 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 74 mg of the title compound. M+1=469; 1H NMR (CD3OD) delta 7.83 (d, 2H), 7.47 (m, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 4.21 (t, 1H), 3.29 (m, 1H), 3.15 (m, 1H).
		3,5-Difluorophenyl-trifluoromethyl ketone was treated with NaBH4 (0.18 g, 4.76 mmol) in THF (5 ml) for 2 hours. The mixture was quenched with water, extracted with methylene chloride (2×). The organics were combined, filtered through silica gel and concentrated to give 0.46 g of 1-(3,4-difluorophenyl)-2,2,2-trifluoroethanol. 1-(3,4-Difluorophenyl)-2,2,2-trifluoroethanol (0.1 g, 0.471 mmol) was treated with NaH (60% in mineral oil, 38 mg, 0.943 mmol) in dry THF (3 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (77 mg, 0.471 mmol) was added and the mixture was stirred at 50 C. for 6 hours. The mixture was quenched with water and extracted with methylenechloride (2×). The organics were combined, washed with water, then brine, dried over MgSO4, and concentrated to give 0.14 g of 4-chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)-pyrimidin-2-amine. 4-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine (0.14 g, 0.421 mmol), L-p-boronophenylalanine (110 mg, 0.505 mmol), Pd(PPh3)2Cl2 (18 mg, 0.025 mmol), Na2CO3 (98 mg, 0.926 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 74 mg of the title compound. M+1=469; 1H NMR (CD3OD) delta 7.83 (d, 2H), 7.47 (m, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 4.21 (t, 1H), 3.29 (m, 1H), 3.15 (m, 1H).

Reference： [1]Patent: US2009/5381,2009,A1
[2]Patent: US2009/29993,2009,A1
[3]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 36

82
[ 945978-67-6 ]
[ 76410-58-7 ]
(2S)-2-Amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;Pd(PPh3)2Cl2; In water; acetonitrile;	4-Chloro-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-2-amine (0.16 g, 0.406 mmol), L-p-boronophenylalanine (10 mg, 0.487 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), Na2CO3 (95 mg, 0.894 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 105 mg of the title compound. M+1=523; 1H NMR (CD3OD) delta 7.85 (d, 2H), 7.70 (d, 1H), 7.44 (m, 4H), 7.31 (t, 1H), 7.21 (m, 2H), 7.10 (m, 2H), 6.87 (q, 1H), 6.84 (s, 1H), 4.25 (t, 1H), 3.30 (m, 1H), 3.18 (m, 1H).
	With sodium carbonate;Pd(PPh3)2Cl2; In water; acetonitrile;	4-Chloro-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-2-amine (0.16 g, 0.406 mmol), L-p-boronophenylalanine (10 mg, 0.487 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), Na2CO3 (95 mg, 0.894 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 105 mg of the title compound. M+1=523; 1H NMR (CD3OD) delta 7.85 (d, 2H), 7.70 (d, 1H), 7.44 (m, 4H), 7.31 (t, 1H), 7.21 (m, 2H), 7.10 (m, 2H), 6.87 (q, 1H), 6.84 (s, 1H), 4.25 (t, 1H), 3.30 (m, 1H), 3.18 (m, 1H).
		To 4'-bromo-2,2,2-trifluoroacetophenone (5.0 g, 19.76 mmol) in THF (50 mls) at 0 C. was added NaBH4 (1.5 g, 39.52 mmol). The mixture was warmed to room temperature and stirred for 1 hour. The reaction was complete by TLC (CH2Cl2). The mixture was quenched with H2O, rotary evaporated to remove most of the THF, and extracted 2 times with CH2Cl2. The organics were combined, washed with brine, concentrated to a small volume and filtered through a plug of silica gel. The silica was washed with CH2Cl2 to elute the product, and the resulting solution was concentrated to give 4.65 g of 1-(4-bromophenyl)-2,2,2-trifluoroethanol. Yield: 92%. 1-(4-Bromophenyl)-2,2,2-trifluoroethanol (0.13 g, 0.525 mmol), m-tolylboronic acid (0.1 g, 0.736 mmol), Fibercat (4.28% Pd, 47 mgs, 0.0157 mmol Pd), K2CO3 (0.22 g, 1.576 mmol), EtOH (3 mls), and H2O (0.5 mls) were combined and heated at 80 C. for 4 hours. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, filtered, concentrated, slurried in CH2Cl2, and chromatographed over silica gel (CH2Cl2) to give 0.1 g of 2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol. Yield: 72%. Alternatively, 1-(4-bromophenyl)-2,2,2-trifluoroethanol (0.98 g, 3.86 mmol), m-tolylboronic acid (0.63 g, 4.63 mmol), Pd(PPh3)2Cl2 (0.16 g, 0.232 mmol Pd), Na2CO3 (0.90 g, 8.49 mmol), AcCN (10 mls), and H2O (10 mls) were combined and heated in the microwave at 150 C. for 10 minutes. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, concentrated, slurried in CH2Cl2, filtered, and chromatographed over silica gel (CH2Cl2) to give 0.80 g of 2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol. Yield: 79%. Alternatively, tetrabutylammoniumfluoride (TBAF 1.0 N in THF 13 uL, 3.3 mg, 0.013 mmol) was added to a mixture of 3-methyl-biphenyl-2-carboxaldehyde (0.25 g, 1.27 mmol) and trifluoromethytrimethyl silane (0.25 g, 1.53 mmol), in THF (1.5 ml) at 0 C. The reaction was warmed to room temperature and stirred for 4 hours. HCl (3.0 N, 2.0 ml) was added, and the mixture was stirred for 3 hours. The mixture was concentrated, dissolved in methylene chloride, filtered through silica gel, and concentrated to give 0.15 g of 2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol. 2,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol (0.15 g, 0.563 mmol) was treated with NaH (60% in mineral oil, 45 mg, 1.12 mmol) in dry THF (5 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (92 mg, 0.5633 mmol) was added and the mixture was stirred at 50 C. for 6 hours. The mixture was quenched with water and extracted with methylenechloride (2×). The organics were combined, washed with water, then brine, dried over MgSO4, and concentrated to give 0.16 g of 4-chloro-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-2-amine. 4-Chloro-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-2-amine (0.16 g, 0.406 mmol), L-p-boronophenylalanine (10 mg, 0.487 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), Na2CO3 (95 mg, 0.894 mmol), MeCN (2.5 ml) and water (2.5 ml) were heated at 150 C. for 5 minutes in a microwave. The mixture was concentrated and purified via prep HPLC to give 105 mg of the title compound. M+1=523; 1H NMR (CD3OD) delta 7.85 (d, 2H), 7.70 (d, 1H), 7.44 (m, 4H), 7.31 (t, 1H), 7.21 (m, 2H), 7.10 (m, 2H), 6.87 (q, 1H), 6.84 (s, 1H), 4.25 (t, 1H), 3.30 (m, 1H), 3.18 (m, 1H).

Reference： [1]Patent: US2009/5381,2009,A1
[2]Patent: US2009/29993,2009,A1
[3]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 37

83
[ 945978-68-7 ]
[ 76410-58-7 ]
(S)-2-Amino-3-(4-(5-(3-(cyclopentyloxy)-4-methoxybenzylamino)pyridin-3-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Sodium triacetoxyl-borohydride (245 mg, 1.16 mmol) was added to the solution of 5-bromo-pyridine-3-amine (100 mg, 0.57 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (127 mg, 0.57 mmol) in 10 ml of 1,2-dicloroethtane (DCE), of HOAc (66 muL, 2 eq. 1.16 mmol) was added, the mixture was stirred overnight at room temperature, followed by addition of 15 ml of DCE. The organic phase was washed with water, and dried over sodium sulfate. The solvent was removed by under reduced pressure to give 200 mg of crude 5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine, which was used for the next step without further purification. An Emrys process vial (2-5 ml) for microwave was charged with 5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine (40 mg, 0.106 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (22 mg, 0.106 mmol) and 2 ml of acetonitrile. Aqueous sodium carbonate (2 ml, 1M) was added to above solution followed by 10 mol percent of dichlorobis(triphenylphosphine)-palladium (II). The reaction vessel was sealed and heated to 180 C. for 10 minutes with a microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol and purified with Prep-LC to give 20 mg of (S)-2-amino-3-(4-(5-3-(cyclophentyloxy-4-methoxy-benzylamino)pyridine-3-yl)phenyl)-propanoic acid. NMR: 1H-NMR (400 MHz, CD3OD): delta 1.59 (m, 2H), 1.7 (m, 6H), 3.17 (m, 1H), 3.3 (m, 1H), 3.75 (s, 3H), 4.2 (dd, 1H) 4.39 (s, 2H), 4.7 (m, 1H), 6.9 (m, 3H), 7.4 (d, 2H), 7.6 (d, 2H), 7.7 (s, 1H), 7.9 (s, 1H), 8.15 (s, 1H); Analytical HPLC: RT 2.69; M+1: 462 (RT: 1.285).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 37-38

84
[ 945978-27-8 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-(4-amino-6-((R)-1-(naphthalen-2-yl)ethylamino)-1,3,5-triazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		A mixture of 2-amino-4,6-dichloro-[1,3,5]triazine (200 mg, 1.21 mmol), (R)-(+)-1-(2-naphthyl)ethylamine (207 mg, 1.21 mmol) and diisopropyl-ethylamine (3.63 mmol) was dissolved in 150 ml of 1,4-dioxane. The solution was refluxed at 90 C. for 3 hours. After the completion of reaction (monitored by LCMS), solvent was removed and the reaction mixture was extracted with CH2Cl2 (100 ml) and H2O (100 ml). The organic layer was separated and washed with H2O (2×100 ml), dried over Na2SO4, and concentrated in vacuo to give crude intermediate. The crude compound was dissolved in 5 ml of MeCN and 5 ml of H2O in a 20 ml microwave reaction vial. To this solution were added L-p-borono-phenylalanine (253 mg, 1.21 mmol), sodium carbonate (256 mg, 2.42 mmol) and catalytic amount of dichlorobis(triphenylphosphine)-palladium(II) (42.1 mg, 0.06 mmol). The mixture was sealed and stirred in the microwave reactor at 150 C. for 5 minutes, followed by the filtration through celite. The filtrate was concentrated and dissolved in MeOH and H2O (1:1) and purified by preparative HPLC using MeOH/H2O/TFA solvent system. The combined pure fractions were evaporated in vacuo and further dried on a lyophilizer to give 238 mg of 2-amino-3-{4-[4-amino-6-(1-naphthalen-2-yl)-ethylamino)-[1,3,5]triazin-2-yl]-phenyl}-propionic acid (yield: 46%, LC: Column: YMC Pack ODS-A 3.0×50 mm, % B=0100%, Gradient time=4 min, Flow Rate=2 ml/min, wavelength=220, Solvent A=90:10 water:MeOH w/0.1% TFA, Solvent B=90:10 MeOH:water w/0.1% TFA, RT=2.785 min, MS: M+1=429). NMR: 1H-NMR (400 MHz, CD3OD): delta 1.65 (d, 3H), 3.22-3.42 (m, 2H), 4.3 (m, 1H), 5.45 (m, 1H), 7.4 (m, 1H), 7.6 (m 4H), 7.8 (m, 4H), 8.2 (m, 2H).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 22
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3684 - 3687
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5229 - 5232

85
[ 1095316-23-6 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-(4-amino-6-((4′-methylbiphenyl-4-yl)methylamino)-1,3,5-triazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 2-amino-4,6-dichloro-[1,3,5]triazine (100 mg, 0.606 mmol), 4'-methyl-biphenyl-4-yl-methylamine (142 mg, 0.606 mmol), and cesium carbonate (394 mg, 1.21 mmol) was dissolved in 1,4-dioxane (1.5 ml) and H2O (1.5 ml) in a 5 ml microwave vial. The mixture was stirred in microwave reactor at 100 C. for 15 minutes. Solvent was removed and the residue was dissolved in CH2Cl2 (20 ml) and washed with H2O (2×20 ml), dried over Na2SO4 and then removed in vacuo. The crude intermediate was then dissolved in 1.5 ml of MeCN and 1.5 ml of H2O in a 5 ml microwave vial. To this solution were added L-p-borono-phenylalanine (126 mg, 0.606 mmol), sodium carbonate (128 mg, 1.21 mmol) and catalytic amount of dichlorobis(triphenylphosphine)-palladium(II) (21.1 mg, 0.03 mmol). The mixture was sealed and stirred in the microwave reactor at 150 C. for 5 minutes followed by the filtration through celite. The filtrate was concentrated and dissolved in MeOH and H2O (1:1) and purified by preparative HPLC using MeOH/H2O/TFA solvent system. The combined pure fractions were evaporated in vacuo and further dried on a lyophilizer to give 21.6 mg of 2-amino-3-(4-{4-amino-6-[(4'-methyl-biphenyl-4-ylmethyl)-amino]-[1,3,5]triazin-2-yl}-phenyl)-propionic acid (LC: Column: YMC Pack ODS-A 3.0×50 mm, % B=0100%, Gradient time=4 min, Flow Rate=2 ml/min, wavelength=220, Solvent A=90:10 water:MeOH w/0.1% TFA, Solvent B=90:10 MeOH:water w/0.1% TFA, RT=3.096 min, MS: M+1=455). 1H NMR (400 MHz, CD3OD) delta 2.33 (s, 3H), 3.24-3.44 (m, 2H), 4.38 (m, 1H), 7.02 (d, 2H), 7.42 (m, 2H), 7.50-7.60 (m, 6H), 8.22 (m, 2H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5229 - 5232
[2]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 22-23

86
[ 945978-19-8 ]
[ 76410-58-7 ]
(S)-2-amino-3-(4-(4-morpholino-6-(naphthalen-2-ylmethylamino)-1,3,5-triazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		A mixture of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (121 mg, 0.516 mmol), C-naphthalen-2-yl-methylamine hydrochloride (100 mg, 0.516 mmol), cesium carbonate (336 mg, 1.03 mmol) was dissolved in 1,4-Dioxane (1.5 ml) and H2O (1.5 ml) in a 5 ml microwave vial. The mixture was stirred in microwave reactor at 180 C. for 600 seconds. Solvent was removed, and the residue was dissolved in CH2Cl2 (10 ml) and washed with H2O (2×10 ml), dried over Na2SO4 and then in vacuo. The residue was purified by preparative HPLC to give 20 mg intermediate (yield 11%, M+1=356). The intermediate was then dissolved in 0.5 ml of MeCN and 0.5 ml of H2O in a 2 ml microwave vial. To this solution were added L-p-borono-phenylalanine (11.7 mg, 0.0562 mmol), sodium carbonate (11.9 mg, 0.112 mmol) and a catalytic amount of dichlorobis(triphenylphosphine)-palladium(II) (2.0 mg, 5%). The mixture was sealed and stirred in the microwave reactor at 150 C. for 5 minutes followed by the filtration through celite. The filtrate was concentrated and dissolved in MeOH and H2O (1:1) and purified by preparative HPLC using MeOH/H2O/TFA solvent system. The combined pure fractions were evaporated in vacuo and further dried on lyophilizer to give 17 mg of 2-amino-3-(4-{4-morpholin-4-yl-6-[(naphthalene-2-ylmethyl)-amino]-[1,3,5]triazin-2-yl}-phenyl)-propionic acid (yield: 63%, LC: Method B, RT=3.108 min, MS: M+1=486).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 23
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5229 - 5232

87
[ 1095316-24-7 ]
[ 76410-58-7 ]
(2S)-2-amino-3-(4-(4-amino-6-(1-(adamantyl)ethylamino)-1,3,5-triazin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 190℃; for 0.333333h;Microwave irradiation;	A solution of adamantine amine (1 equivalent), 2-amino-4,6-dichloro-[1,3,5]triazine (1 equivalent) and diisopropyl ethyl amine (5 equivalents, Aldrich) in anhydrous 1,4-dioxane was refluxed at 130 C. for 3 hours. After completion of the reaction, the dioxane was removed under reduced pressure. The reaction was then cooled to room temperature, water was added, and product was extracted with dichloromethane (2×40 ml). The combined organic solution was dried over Na2SO4 and concentrated to afford product, which was used in the next step without purification. An Emrys process vial (20 ml) for microwave was charged with adamantine trizine chloride (200 mg, 0.65 mmol), <strong>[76410-58-7]4-borono-L-phenylalanine</strong> (135 mg, 0.65 mmol) and 5 ml of acetonitrile. Aqueous sodium carbonate (5 ml, 1M) was added to above solution followed by 5 mol percent dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 190 C. for 20 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 4 ml of methanol and purified with Prep-LC to give 60 mg (yield 21%) of coupled product. NMR: 1H-NMR (400 MHz, CD3OD): delta 1.22 (m, 3H), 1.6-1-8 (m, 12H), 2.01 (d, 3H), 3.25-3.42 (m, 2H), 4.0 (m, 1H), 4.40 (m, 1H), 7.6 (d, 2H), 8.2 (d, 2H), Analytical HPLC: RT 3.11, M+1: 437 (RT: 1.76).

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 39
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5229 - 5232

88
[ 1095316-30-5 ]
[ 76410-58-7 ]
(S)-2-Amino-3-(4-(5-fluoro-4-((R)-1-(naphthalen-2-yl)ethylamino)pyrimidin-2-yl)phenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of (R)-(+)-1-(2-napthyl)ethylamine (102.6 mg, 0.599 mmol), 2,4-dichloro-5-fluroro pyrimidine (100 mg, 0.599 mmol) and cesium carbonate (390 mg, 1.2 mmol) was dissolved in 1,4-dioxane (3 ml) and H2O (3 ml) in a 10 ml microwave vial. The mixture was stirred in the microwave reactor at 80 C. for 10 minutes. The residue was dissolved in CH2Cl2 (50 ml), washed with water (20 ml), brine (20 ml) dried (Na2SO4) and concentrated to get the crude intermediate 2-chloro-5-fluoro-pyrimidin-4-yl)-(1-naphthalen-2-yl-ethyl)-amine. The crude intermediate (250 mg, 0.83 mmol) was then dissolved in 6.0 ml of MeCN and 6 ml of H2O in a 20 ml microwave vial. To this solution were added L-p-borono-phenylalanine (173.6 mg, 0.83 mmol), sodium carbonate (173.6 mg, 1.66 mmol) and catalytic amount of dichlorobis(triphenylphosphine)-palladium(II) (11.6 mg, 0.0166 mmol). The reaction vial was then sealed and stirred in the microwave reactor at 150 C. for 7 minutes. The contents were then filtered, and the filtrate was concentrated and dissolved in MeOH and H2O (1:1) and purified by preparative HPLC using MeOH/H2O/TFA as the solvent system. The combined pure fraction were evaporated in vacuo and further dried on a lyophilizer to give 154 mg of 2-amino-3-{4-[5-fluoro-4-(1-naphthalen-2-yl-ethylamino)-pryrimidin-2-yl]-phenyl}-propionic acid. NMR: 1H-NMR (400 MHz, CD3OD) delta 1.8 (d, 3H) 3.2-3.4 (m, 2H), 4.35 (m, 1H), 5.7 (q, 1H), 7.5 (m, 4H), 7.6 (d, 1H), 7.8-7.9 (m, 4H), 8.1 (d, 2H), 8.3 (d, 1H). LCMS:M+1=431.

Reference： [1]Patent: US2007/191370,2007,A1 .Location in patent: Page/Page column 39-40

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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 76410-58-7 ] {[proInfo.proName]}

Quality Control of [ 76410-58-7 ]

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[ 76410-58-7 ] Synthesis Path-Upstream 1~21

[ 76410-58-7 ] Synthesis Path-Downstream 1~88

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Related Functional Groups of [ 76410-58-7 ]

Amino Acid Derivatives

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[ 76410-58-7 ]

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