[ CAS No. 20010-99-5 ]

Name: 20010-99-5|Pyrazin-2-ylmethanamine|98%
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Quality Control of [ 20010-99-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 20010-99-5 ]

CAS No. :	20010-99-5	MDL No. :	MFCD00673149
Formula :	C₅H₇N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HQIBSDCOMQYSPF-UHFFFAOYSA-N
M.W :	109.13	Pubchem ID :	266781
Synonyms :

Calculated chemistry of [ 20010-99-5 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	29.71
TPSA :	51.8 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) :	-7.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.85
Log Po/w (XLOGP3) :	-1.3
Log Po/w (WLOGP) :	-0.22
Log Po/w (MLOGP) :	-1.39
Log Po/w (SILICOS-IT) :	0.55
Consensus Log Po/w :	-0.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.19
Solubility :	71.0 mg/ml ; 0.651 mol/l
Class :	Very soluble
Log S (Ali) :	0.71
Solubility :	560.0 mg/ml ; 5.13 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.63
Solubility :	2.53 mg/ml ; 0.0232 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 20010-99-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P264-P270-P301+P310-P321-P330-P405-P501	UN#:	2810
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 20010-99-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 20010-99-5 ]
Downstream synthetic route of [ 20010-99-5 ]

[ 20010-99-5 ] Synthesis Path-Upstream 1~5

1
[ 19847-12-2 ]
[ 20010-99-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Ni-doped silica; hydrogen In toluene at 140℃; for 4 h; Autoclave; Inert atmosphere	The synthesis of 2-aminomethyl pyradine(2-AMPZ) was carried out by a method shown below, byreference to the method described in literature (JP A 2001-894594). 2-cyanopyradine used was from Sigma-Aldrich Co.LLC.1.05 g of 2-cyanopyradine (10 mmol) and 100mg of60 wt percent-Ni/5i02 were placed in an autoclave (5U53 16) with20 mL of toluene and replaced with argon gas. This waspressurized with hydrogen gas to 50 atm, stirred at 140°C. for4 hours. The reaction solution was filtered and concentratedto give 2-aminomethyl pyradine (2-AMPZ) quantitatively.10152] ‘H-NMR spectrum (399.78 MHz, CDC13):ö8.60-8.45 (m, 3H), 4.07 (s, 2H), 1.79 (br, 2H)
98%	With hydrogen In 1,4-dioxane at 60℃; for 8 h; Autoclave	Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane under stirring, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was hydrogenated for 8 hours under 40 atmosphere at 60 °C, filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methylamine 1h (10.7 g, yield 98percent) as a brown oil. MS m/z (ESI): 110 [M+1]
98%	With hydrogen In 1,4-dioxane at 60℃; for 8 h; Autoclave	Step 6 C-Pyrazin-2-yl-methylamine Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was reacted in hydrogen atmosphere for 8 hours under 40 atmosphere at 60 °C and filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methyl amine 1h (10.7 g, yield 98percent) as a brown oil. MS m/z (ESI): 110 [M+1].

98%	With hydrogen In 1,4-dioxane at 60℃; for 8 h;	Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was reacted in hydrogen atmosphere for 8 hours under 40 atmosphere at 60° C. and filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methyl amine 1h (10.7 g, yield 98percent) as a brown oil. MS m/z (ESI): 110 [M+1].
98%	With pyridine; hydrogen In 1,4-dioxane at 60℃; for 8 h; Autoclave	2-cyano-pyrazol 1g (10.5 g, 100 mmol) was dissolved in 150 mL 1,4- dioxane was added 1.0 g Raney nickel in 250 mL autoclave at 60 , 40 atm of hydrogen the reaction was stirred for 8 hours. Filtered, and the filtrate was concentrated under reduced pressure, to give C- pyridin-2-yl - methylamine 1h (10.7 g, brown oil). Yield: 98percent.
98.9%	With hydrogen In 1,4-dioxane at 60℃; for 48 h;	Pyrazine-2-carbonitrile (19 g, 180 mmol) was dissolved in 1,4-dioxane (280 mL), and then Raney nickel (1.9 g) was added. The reaction mixture was reacted in hydrogen atmosphere at 60°C for 48 hours. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to obtain the title compound (1) (19 g, 98.9percent) as a brown oil. 1H MR (400 MHz, DMSO-d₆): δ 871 (s, 1H), 8.54-8.53 (m, 2H), 8.48 (d, J = 2.4Hz, 1H), 3.86 (s, 2H), 1.97 (br, 2H).

Reference： [1] Patent: US2015/31920, 2015, A1, . Location in patent: Paragraph 0150; 0151; 0152
[2] Patent: EP2230241, 2010, A1, . Location in patent: Page/Page column 18
[3] Patent: EP2404921, 2012, A1, . Location in patent: Page/Page column 9
[4] Patent: US2012/65209, 2012, A1, . Location in patent: Page/Page column 9
[5] Patent: TWI522358, 2016, B, . Location in patent: Page/Page column 15; 18
[6] Patent: WO2018/175512, 2018, A1, . Location in patent: Page/Page column 21
[7] Synlett, 2001, # 10, p. 1623 - 1625
[8] Patent: WO2005/66126, 2005, A1, . Location in patent: Page/Page column 61-62
[9] Patent: WO2006/108103, 2006, A1, . Location in patent: Page/Page column 30
[10] Patent: US2008/119496, 2008, A1, . Location in patent: Page/Page column 10
[11] Patent: WO2008/60301, 2008, A1, . Location in patent: Page/Page column 29

2
[ 20584-30-9 ]
[ 20010-99-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	for 1 h; Reflux	B. A suspension of 2-(pyrazin-2-ylmethyl)isoindoline-1 ,3-dione (3.56 g, 14.9 mmol) in 5 N aqueous sodium hydroxide (180 mL) was heated at reflux for 1 h, allowed to cool to ambient temperature extracted with dichloromethane (4 x 50 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford pyrazin-2-ylmethanamine as a yellow oil in 67percent yield (1.09 g), which was used without further purification: ¹H NMR (300 MHz, CDCI₃) £8.55 (br s, 1 H), 8.49-8.47 (m, 1 H), 8.42 (d, J = 2.4 Hz, 1 H), 3.99 (s, 2H), 1.66 (s, 2H); MS (ES+) m/z 109.7 (M + 1).

Reference： [1] Patent: WO2013/64984, 2013, A1, . Location in patent: Page/Page column 65
[2] Supramolecular Chemistry, 2018, vol. 30, # 4, p. 296 - 304

3
[ 6164-79-0 ]
[ 20010-99-5 ]

Reference： [1] Supramolecular Chemistry, 2018, vol. 30, # 4, p. 296 - 304

4
[ 6705-33-5 ]
[ 20010-99-5 ]

Reference： [1] Supramolecular Chemistry, 2018, vol. 30, # 4, p. 296 - 304

5
[ 39204-47-2 ]
[ 20010-99-5 ]

Reference： [1] Patent: WO2013/64984, 2013, A1,

[ 20010-99-5 ] Synthesis Path-Downstream 1~68

1
[ 23316-68-9 ]
[ 20010-99-5 ]
[ 90176-04-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 229 - 238

2
[ 1452-94-4 ]
[ 20010-99-5 ]
2-[(pyrazin-2-ylmethyl)-amino]-nicotinic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

3
[ 20010-99-5 ]
[ 900145-11-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

4
[ 20010-99-5 ]
{3-[5-(benzo[1,3]dioxol-5-ylamino)-[1,3,4]oxadiazol-2-yl]-pyridin-2-yl}-pyrazin-2-ylmethyl-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

5
[ 20010-99-5 ]
{3-[5-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-[1,3,4]oxadiazol-2-yl]-pyridin-2-yl}-pyrazin-2-ylmethyl-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

6
[ 20010-99-5 ]
[ 900144-41-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

7
[ 20010-99-5 ]
[ 900144-40-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

8
[ 20010-99-5 ]
[ 90176-23-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 229 - 238

9
[ 20010-99-5 ]
[ 90176-14-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 229 - 238

10
[ 859164-51-5 ]
[ 20010-99-5 ]
4-(3-phenyl-indole-1-sulfonyl)-N-pyrazin-2-ylmethyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃; for 18h;	Example 70; 4- (3-Phenvl-indole-1-sulfoni)-N-pyrazin-2-Imethvl-benzamide; Add 10ml dry DMF to a flask under N2 containing 4- (3-Phenyl-indole-l- sulfonyl)-benzoic acid (500mg, 1. 33mmol, 1. Oeq), 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (279mg, 1. 46mmol, 1.1 eq), Dimethyl-pyridin-4-yl- amine (16mg,. 132mmol,. 1 eq), and C-Pyrazin-2-yl-methylamine (217mg, 1. 99mmol, 1.5 eq). Stir for 18 hours at room temperature. Remove solvent on rotovap and purify by silca gel chromatography to give 4- (3-Phenyl-indole-l-sulfonyl)-N-pyrazin-2-ylmethyl- benzamide (127mg, 20% yield). Mass Spectrum (m/e): 468.95 (MH+).

Reference： [1]Patent: WO2005/66126,2005,A1 .Location in patent: Page/Page column 105

11
[ 117-80-6 ]
[ 20010-99-5 ]
[ 354824-12-7 ]

Yield	Reaction Conditions	Operation in experiment
88.0%	With triethylamine; In ethanol; at 20℃; for 18h;	General procedure: To 2,3-dichloro-1,4-naphthoquinone (0.341g, 1.50mmol) in 1.5mlof ethanol was added 2-methoxyethylamine (0.124g, 1.65mmol) and triethylamine (0.227g,2.25mmol) and the mixture stirred at r. t. for 18h. The red precipitate formedwas filtered under suction, washed with distilled water and dried to afford (4) as a dark red solid, 87.8%.
	With N-ethyl-N,N-diisopropylamine; In water; benzene;	REFERENCE EXAMPLE 4 <strong>[20010-99-5]2-(Aminomethyl)pyrazine</strong> (3.2 g) and diisopropylethylamine (5.8 ml) were added to a solution of 2,3-dichloro-1,4-dihydro-1,4-dioxonaphthalene (3.0 g) in benzene (90 ml) and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction solution and the resulting precipitate was removed by filtration and then the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution with chloroform) to give 2-chloro-1,4-dihydro-1,4-dioxo-3-[(2-pyrazinylmethyl)amino]naphthalene (0.23 g) as a light brown powder.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]Patent: US2003/114508,2003,A1
[3]ChemMedChem,2016,p. 1944 - 1955

12
[ 24424-99-5 ]
[ 20010-99-5 ]
[ 1026790-47-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In isopropyl alcohol; at 20℃; for 2h;	To a solution of 2-aminomethyl-pyrazine (5.0 g, 45.87 mmol) in isopropanol (50 ml) was added di-tert-butyl-pyrocarbonate (12.0 g, 55.84 mmol); the mixture was stirred at ambient temperature for 2 h. Next, the solvent was evaporatedand the residue was dissolved in DCM (30 ml), and subjected to silica gel purification (chloroformlmethanol gradient 0-30% in 100 mm.). Fractions containing desired product were combined and evaporated. Residue was dried under vacuum to provide Compound AA in quantitative yield(10.22 g, 99% purity) as amorphous solid. LC-MS: (mlz) observed (M+H) 210.5 (C10H15N302+H calc: 210.3)
	In dichloromethane;	Example 8. Synthesis of the primary amine, pyrazin-2-ylmethanaminechromatography 17 3. TFA / CH2CI2 18[0096] Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-fert-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate:methanol) provided 0.5O g of pure tert-butyl pyrazin-2-ylmethylcarbamate. Pure pyrazin-2- ylmethanamine (18) was obtained as the TFA salt from deprotection of the carbamate with 1:1 TFA / CH2Cl2. EPO <DP n="33"/>[0097]
	In dichloromethane;	Example 8 Synthesis of the primary amine, pyrazin-2-ylmethanamine Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-tert-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate:methanol) provided 0.50 g of pure tert-butyl pyrazin-2-ylmethylcarbamate.

In dichloromethane;

Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-terf-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate methanol) provided 0.50 g of pure tert-butyl pyrazin-2-ylmethylcarbamate. Pure pyrazin-2-yhnethanamine (18) was obtained as the TFA salt from deprotection of the carbamate with 1:1 TFA / CH2Cl2.

Reference： [1]Patent: US9139612,2015,B2 .Location in patent: Page/Page column 151
[2]Patent: WO2006/108103,2006,A1 .Location in patent: Page/Page column 30
[3]Patent: US2008/119496,2008,A1 .Location in patent: Page/Page column 10
[4]Patent: WO2008/60301,2008,A1 .Location in patent: Page/Page column 29

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 6-methyl-N-(2-pyrazinylmethyl)ergoline-8beta-carboxamide In an analogous manner to that described in Example 1, 6-methyl-N-(2-pyrazinylmethyl)ergoline-8beta-carboxamide is prepared from aminomethylpyrazine (obtained according to J. Org. Chemistry 38, 2049 (1973)) as a starting compound. After pouring onto a 2N-soda solution and extracting with methylene chloride and evaporating the solvent, the crude product is purified by chromatography on a column of silica gel using methylene chloride/methanol/concentrated ammonia (93:7:0.7) as the eluant. The pure product is crystallized from ethanol/n-hexane. Decomposition without melting above 194. [alpha]D20 =-93.0 (c=1,0 in dimethylformamide).

14
[ 20010-99-5 ]
[ 71064-26-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 10 Preparation of 1-Amino-3-(pyrazinylmethyl)guanidine hydriodide A solution of 3.66 g. of methyl thiocarbazimidate hydriodide and 3.42 g. of (aminomethyl)pyrazine [A. Hirschberg and P. Mattner, J. Med. Chem., 11, 911 (1961)] in 50 ml. of absolute ethanol is heated at reflux for 20 hours and then concentrated to dryness under reduced pressure to give the desired product as an orange solid.

Reference： [1]Patent: US4154947,1979,A

15
[ 4548-45-2 ]
[ 20010-99-5 ]
5-nitro-N-(2-pyrazinylmethyl)-pyridin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran;	Preparation 103 To a solution of <strong>[20010-99-5]2-aminomethylpyrazine</strong> (2.18g) and triethylamine (4.05g) in tetrahydrofuran (50ml) was added 2-chloro-5-nitropyridine (3.17g). The mixture was stirred at 60C for 6 hours, poured into ice-water and stirred for 10 minutes. The precipitate was collected by filtration, washed with water and dried to give 5-nitro-N-(2-pyrazinylmethyl)-2-pyridylamine (4.06g). APCI-mass;m/z232.20(M+H+) 1H-NMR(DMSO-d6): delta;4.78(2H,d,J=5.9Hz), 6.72(1H,d,J=9.4Hz), 8.16(1H,dd, J=2.8Hz,9.4Hz), 8.5-8.9(4H,m), 8.89(1H,d,J=2.8Hz)

Reference： [1]Patent: EP1264820,2002,A1

16
copper(II) perchlorate hexahydrate [ No CAS ]
[ 75-05-8 ]
[ 20010-99-5 ]
[Cu(2-pyrazine carboxamide)(MeCN)3](ClO₄)2*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2005,vol. 8,p. 680 - 683

17
[ 442910-19-2 ]
[ 20010-99-5 ]
C₁₃H₁₁N₇O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 33 - 47

18
[ 530089-00-0 ]
[ 20010-99-5 ]
[ 1158945-82-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3130 - 3141

19
[ 1238062-32-2 ]
[ 20010-99-5 ]
[ 1238062-35-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4547 - 4559

20
[ 1238062-50-4 ]
[ 20010-99-5 ]
[ 1238062-57-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4547 - 4559

21
[ 1238062-21-9 ]
[ 20010-99-5 ]
[ 1238062-25-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4547 - 4559

22
[ 407-25-0 ]
[ 20010-99-5 ]
[ 1152439-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 0 - 20℃; for 3h;Cooling with ice;	C-Pyrazin-2-yl-methylamine 1h (10.9 g, 100 mmol) was added into a reaction flask, then 20 mL of trifluoroacetic anhydride was added dropwise slowly within an hour at 0 C in an ice-water bath. The reaction mixture was reacted at room temperature for 2 hours and monitored by thin layer chromatography until the disappearance of the starting materials. Then it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 2,2,2-trifluoro-N-pyrazin-2-ylmethyl-acetamide 1i (21.0 g) as a brown oil. MS m/z (ESI): 206.1 [M+1]
	at 0 - 20℃; for 3h;	Step 7 2,2,2-Trifluoro-N-pyrazin-2-ylmethyl-acetamide C-Pyrazin-2-yl-methylamine 1h (10.9 g, 100 mmol) was added into a reaction flask, then 20 mL of trifluoroacetic anhydride was added dropwise slowly within an hour at 0C in an ice-water bath. The reaction mixture was reacted at room temperature for 2 hours. Then the mixture was concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography with system A as eluant to obtain the title compound 2,2,2-trifluoro-N-pyrazin-2-ylmethyl-acetamide 1i (21.0 g) as a brown oil. MS m/z (ESI): 206.1 [M+1].
	at 0 - 20℃; for 3h;	C-Pyrazin-2-yl-methylamine 1 h (10.9 g, 100 mmol) was added into a reaction flask, then 20 mL of trifluoroacetic anhydride was added dropwise slowly within an hour at 0 C. in an ice-water bath. The reaction mixture was reacted at room temperature for 2 hours. Then the mixture was concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography with system A as eluant to obtain the title compound 2,2,2-trifluoro-N-pyrazin-2-ylmethyl-acetamide 1i (21.0 g) as a brown oil. MS m/z (ESI): 206.1 [M+1].

21.0 g	at 20℃; for 3h;Cooling with ice;	The C- pyridin-2-yl - methylamine 1h (10.9 g, 100 mmol) was added to the reaction flask under ice bath, was added dropwise over 1 hour 20 mL of trifluoroacetic anhydride, the reaction was stirred at room temperature for 2 hours, The reaction solution was concentrated under reduced pressure, column chromatography using silica gel eluting with system A was obtained residue was purified to give the title product 2,2,2-trifluoro-2-methyl -N- pyridin - formamide 1i ( 21.0 g, brown oil).
	at 0 - 20℃; for 12h;	In the 0 C lower, will be C - pyrazine -2 - yl - amine (5 g, 45.9 mmol) is added to the reaction flask, slowly dropping 9.8 ml trifluoroacetic anhydride, stir at room temperature 12 hours, the reaction solution is concentrated under reduced pressure, to obtain the title product trifluoro acetyl pyrazine -2 - methylamine (15 g crude, brown oily matter), directly used for the next step reaction.

Reference： [1]Patent: EP2230241,2010,A1 .Location in patent: Page/Page column 18
[2]Patent: EP2404921,2012,A1 .Location in patent: Page/Page column 9
[3]Patent: US2012/65209,2012,A1 .Location in patent: Page/Page column 9
[4]Patent: TWI522358,2016,B .Location in patent: Page/Page column 15; 18
[5]Patent: CN106478631,2017,A .Location in patent: Paragraph 0098

23
C₂₁H₁₉ClN₂O₅ [ No CAS ]
[ 20010-99-5 ]
C₂₆H₂₆ClN₅O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7715 - 7730

24
[ 1300031-57-5 ]
[ 20010-99-5 ]
C₂₁H₂₀N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 48: 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1 -(2-pyrazinylmethyl)-1 ,3- dihydro-2H-imidazo[4,5-c]quinolin-2-one; In a 100ml flask a mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3- quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg,) and (2- pyrazinylmethyl)amine (2.5 eq) in acetonitrile was heated at 100C for 2h. The reaction mixture was hydrolyzed with a solution of sodium hydrogen carbonate, extracted with DCM and the organic dried over Na2S04, filtered and concentrated to dryness to give the crude intermediate. The residue was dissolved in acetonitrile (15ml), bis(trifluoroacetoxy)iodo]benzene (0.5g) was added and the reaction mixture was stirred for 3h at room temperature. The reaction mixture was washed with water, extracted with DCM and the organic were dried over Na2S04, filtered and concentrated to dryness. The resulting crude compound was purified by chromatography on silica gel eluting with DCM / methanol (95:5) and the resulting residue was recrystallised from acetonitrile and dried in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1 -(2-pyrimidinylmethyl)-1 ,3- dihydro-2H-imidazo[4,5-c]quinolin-2-one (100mg) as a beige powder.LC-HRMS: ES+ exact mass calculated for C2i H19N603 403.1519 MH+, found: 403.1550, Rt 2.06min.
	In acetonitrile; at 100℃; for 2h;	In a 100 ml flask a mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg,) and (2-pyrazinylmethyl)amine (2.5 eq) in acetonitrile was heated at 100 C. for 2 h. The reaction mixture was hydrolyzed with a solution of sodium hydrogen carbonate, extracted with DCM and the organic dried over Na2SO4, filtered and concentrated to dryness to give the crude intermediate.

Reference： [1]Patent: WO2011/54846,2011,A1 .Location in patent: Page/Page column 91
[2]Patent: US2012/232074,2012,A1 .Location in patent: Page/Page column 41-42

25
[ 1309366-06-0 ]
[ 20010-99-5 ]
C₂₉H₃₃N₅O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5836 - 5857

26
[ 20010-99-5 ]
[ 1174122-63-4 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

27
[ 20010-99-5 ]
(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid phosphate [ No CAS ]

Reference： [1]Patent: TWI522358,2016,B

28
[ 20010-99-5 ]
[ 1242332-62-2 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

29
[ 20010-99-5 ]
[ 1242332-70-2 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

30
[ 20010-99-5 ]
[ 1242332-77-9 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

31
[ 20010-99-5 ]
[ 1242332-81-5 ]

Reference： [1]Patent: US2012/65209,2012,A1

32
[ 20010-99-5 ]
[ 959238-36-9 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B
[3]Patent: CN106478631,2017,A

33
[ 20010-99-5 ]
[ 959238-29-0 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

34
[ 20010-99-5 ]
[ 1152439-77-4 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

35
[ 20010-99-5 ]
[ 1152440-32-8 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

36
[ 20010-99-5 ]
[ 1174039-18-9 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

37
[ 20010-99-5 ]
[ 1174039-19-0 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

38
[ 20010-99-5 ]
(R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid hydrochloride [ No CAS ]

Reference： [1]Patent: US2012/65209,2012,A1

39
[ 20010-99-5 ]
[ 1242332-63-3 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

40
[ 20010-99-5 ]
[ 1242332-64-4 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

41
[ 20010-99-5 ]
(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylate calcium salt [ No CAS ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

42
[ 20010-99-5 ]
[ 1242332-84-8 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

43
[ 20010-99-5 ]
[ 1242332-69-9 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

44
[ 20010-99-5 ]
[ 1242332-75-7 ]

Reference： [1]Patent: US2012/65209,2012,A1
[2]Patent: TWI522358,2016,B

45
[ 20010-99-5 ]
(R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid phosphate [ No CAS ]

Reference： [1]Patent: US2012/65209,2012,A1

46
[ 24424-99-5 ]
[ 20010-99-5 ]
pyrazin-2-ylmethyl-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; isopropyl alcohol;	Synthesis of pyrazin-2-ylmethyl-carbamic acid tert-butyl ester (Compound AA) To a solution of 2-aminomethyl-pyrazine (5.0 g, 45.87 mmol) in isopropanol (50 ml) was added di-tert-butyl-pyrocarbonate (12.0 g, 55.84 mmol); the mixture was stirred at ambient temperature for 2 h. Next, the solvent was evaporated and the residue was dissolved in DCM (30 ml), and subjected to silica gel purification (chloroform/methanol gradient 0->30% in 100 min.). Fractions containing desired product were combined and evaporated. Residue was dried under vacuum to provide Compound AA in quantitative yield (10.22 g, 99% purity) as amorphous solid. LC-MS: (m/z) observed (M+H+) 210.5 (C10H15N3O2+H calc: 210.3).
	In isopropyl alcohol;	Synthesis of pyrazin-2-ylmethyl-carbamic acid tert-butyl ester (Compound AA) To a solution of 2-aminomethyl-pyrazine (5.0 g, 45.87 mmol) in isopropanol (50 ml) was added di-tert-butyl-pyrocarbonate (12.0 g, 55.84 mmol); the mixture was stirred at ambient temperature for 2 h. Next, the solvent was evaporated and the residue was dissolved in DCM (30 ml), and subjected to silica gel purification (chloroform/methanol gradient 0->30% in 100 min.). Fractions containing desired product were combined and evaporated. Residue was dried under vacuum to provide Compound AA in quantitative yield (10.22 g, 99% purity) as amorphous solid. LC-MS: (m/z) observed (M+H+) 210.5 (C10H15N3O2+H calc: 210.3).

Reference： [1]Patent: US2012/295834,2012,A1
[2]Patent: US8685916,2014,B2 .Location in patent: Page/Page column

47
[ 16232-01-2 ]
[ 126-81-8 ]
[ 20010-99-5 ]
2,5-bis-(4-bromophenyl)-8,8-dimethyl-1-pyrazin-2-yl-3-(pyridine-2-carbonyl)-3a-pyridin-2-yl-2,3,3a,4,5,7,8,9-octahydro-1H-pyrrolo[1,2-a]quinolin-6-one [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 11966 - 11968

48
[ 126-81-8 ]
[ 34064-90-9 ]
[ 20010-99-5 ]
2,5-bis-(4-chlorophenyl)-8,8-dimethyl-3-(pyrazine-2-carbonyl)-1-pyrazin-2-yl-3a-pyrazin-2-yl-2,3,3a,4,5,7,8,9-octahydro-1H-pyrrolo[1,2-a]quinolin-6-one [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 11966 - 11968

49
[ 20584-30-9 ]
[ 20010-99-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With water; sodium hydroxide; for 1h;Reflux;	B. A suspension of 2-(pyrazin-2-ylmethyl)isoindoline-1 ,3-dione (3.56 g, 14.9 mmol) in 5 N aqueous sodium hydroxide (180 mL) was heated at reflux for 1 h, allowed to cool to ambient temperature extracted with dichloromethane (4 x 50 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford pyrazin-2-ylmethanamine as a yellow oil in 67% yield (1.09 g), which was used without further purification: 1H NMR (300 MHz, CDCI3) £8.55 (br s, 1 H), 8.49-8.47 (m, 1 H), 8.42 (d, J = 2.4 Hz, 1 H), 3.99 (s, 2H), 1.66 (s, 2H); MS (ES+) m/z 109.7 (M + 1).
	With hydrazine hydrate; In ethanol; for 2h;Reflux;	2-Pyrazinemethylphthalimide(0.15 g, 0.63 mmol) was suspended in ethanol (10 mL) andhydrazine hydrate (80% w/w%, 1.5 mL, 3.1 mmol) addedbefore the suspension was heated to reflux for two hours.The suspension was then cooled to room temperaturethen further cooled in the fridge. The suspension wasfiltered and the filtrate taken to dryness yielding 2-(aminomethyl)pyrazine as a yellow oil that was used without further purification (0.05 g, ca. 74%). Found: C, 52.70; H,6.60; N, 36.43. Calculated for C5H7N3O·H2O: C, 52.43; H,6.69; N, 36.69. 1H NMR (300 MHz, CDCl3): delta (ppm) 8.54 (d,J = 1.5 Hz, 1H, H-3), 8.46 (dd, J = 1.5, 2.7 Hz, 1H, H-2), 8.40(d, J1,2 = 2.7 Hz, 1H, H-1), 3.96 (s, 2H, CH2).

Reference： [1]Patent: WO2013/64984,2013,A1 .Location in patent: Page/Page column 65
[2]Supramolecular Chemistry,2018,vol. 30,p. 296 - 304

50
[ 15216-81-6 ]
[ 20010-99-5 ]
[ 1432912-54-3 ]

Yield	Reaction Conditions	Operation in experiment
0.379 g	With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;Reflux;	C. To a suspension of 5-chlorosalicylic acid (0.96 g, 5.6 mmol) in dichloromethane (13 mL) was added thionyl chloride (2 mL, 28 mmol) and N,N- dimethylformamide (~3 drops). The reaction mixture was heated at reflux for 1 h, at which point a clear solution was obtained. The mixture was allowed to cool to ambient temperature and was concentrated in vacuo. The residue was dissolved in dichloromethane (10 mL), and pyrazin-2-ylmethanamine (0.80 g, 4.6 mmol), N,N- diisopropylethylamine (1.6 mL, 9.3 mmol), and 4-(W,W-dimethylamino)pyridine (0.056 m, 0.5 mmol) were added. The reaction mixture was stirred at ambient temperature for 16 h, diluted with dichloromethane (70 mL) and washed with 1 N hydrochloric acid (2 x 7 mL), water (2 x 7 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography eluting with a 10-60% gradient of ethyl acetate in hexanes to afford 5-chloro-2-hydroxy-A/-(pyrazin-2-ylmethyl)benzamide as a yellow solid in 31 % yield (0.379 g): 1H NMR (300 MHz, CDCI3) £ 12.10 (s, 1 H), 8.67 (s, 1 H), 8.57 (s, 2H), 7.57 (br s, 1H), 7.46 (d, J = 2.1 Hz, 1 H), 7.34 (dd, J = 8.9, 1.8 Hz, 1H), 6.93 (d, J = 8.9 Hz, 1 H), 4.78 (d, J = 4.8 Hz, 2H); MS (ES+) m/z 264.0 (M + 1 ), 266.0 (M + 1 ).

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 277 - 282
[2]Patent: WO2013/64984,2013,A1 .Location in patent: Page/Page column 65

51
[ 15216-81-6 ]
[ 20010-99-5 ]
[ 1432912-53-2 ]

Reference： [1]Patent: WO2013/64984,2013,A1

52
[ 39204-47-2 ]
[ 20010-99-5 ]

Reference： [1]Patent: WO2013/64984,2013,A1

53
[ 1439358-24-3 ]
[ 20010-99-5 ]
[ 1439358-05-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3531 - 3538

54
[ 1076-38-6 ]
[ 16231-98-4 ]
[ 20010-99-5 ]
2,7-bis(4-chlorophenyl)-6-(2-hydroxybenzoyl)-1-picolinoyl-3-(pyrazin-2-yl)-8a-(pyridin-2-yl)hexahydroindolizin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11414 - 11420

55
[ 1076-38-6 ]
[ 92963-52-5 ]
[ 20010-99-5 ]
2,7-bis(2,3-dimethoxyphenyl)-6-(2-hydroxybenzoyl)-1-picolinoyl-3-(pyrazin-2-yl)-8a-(pyridin-2-yl)hexahydroindolizin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11414 - 11420

56
[ 6164-79-0 ]
[ 20010-99-5 ]
(2-pyrazylmethyl)-2-pyrazinecarboxamide [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 2880 - 2892

57
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-(pyrazin-2-ylmethyl)acetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-pyrazin-2-ylmethylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.1%	With triethylamine; In toluene; at 50℃; for 3h;	To a suspension of (17) (0.809g, 2.4mmol) in 3mL of toluene, pyrazin-2-ylmethylamine(0.338g, 3.1mmol) then triethylamine (0.364g, 3.6mmol) was added drop-wise andstirred at 50C for 3h. The toluene was evaporated in vacuo. Reaction mixture was filtered under vacuum suction,washed with distilled water and EtOH and dried to afford (61) as an orange solid, 96.1%.1H (CDCl3) delta 8.80 (s, 1H),8.63 (s, 1H), 8.53 (s, 2H), 8.41 (d, 1H, J=2.56Hz),8.21 (s, 1H), 8.10 (d, 1H, J=7.62Hz),8.04 (d, 1H, J=7.60Hz), 7.76 (dt, 1H,J=1.29, 7.57Hz), 7.66 (dt, 1H, J=1.24, 7.54Hz), 2.00 (s, 4H)), 1.26 (s,3H); 13C (CDCl3) delta 155.58, 155.04, 143.97, 143.84,143.80, 143.74, 143.46, 142.88, 135.03, 132.64, 132.01, 126.61, 126.45, 124.83,107.41, 52.55, 29.58, 29.31.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

58
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-(2-ethoxyethyl)acetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-(2-ethoxyethyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.7%	With triethylamine; In toluene; at 50℃; for 3h;	To a suspension of (18) (0.483g, 1.50mmol) in 2mL of toluene, pyrazin-2-ylmethylamine(0.236g, 2.25mmol) then triethylamine (0.227g, 2.25mmol) was added drop-wiseand stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extractedwith EtOAc, washed with brine and dried over anhydrous Na2SO4.Purification by column (EtOAc/Hexane 1:1) afforded (51) as a red oil, 24.7%.1H (CDCl3) delta 8.64(d, 1H, J=1.11Hz), 8.59-8.61 (m, 1H),8.55 (d, 1H, J=2.51Hz), 8.14 (dd, 1H,J=0.71, 7.65Hz), 8.09 (d, 1H, J=7.63Hz), 7.77 (dt, 1H, J=1.27. 7.58Hz), 7.67 (dt, 1H, J=1.26, 7.56Hz), 7.59 (br s, 1H), 4.87-5.12(m, 2H), 3.74-3.79 (m, 2H), 3.48-3.53 (m, 2H), 3.27-3.39 (m, 2H), 1.97 (s, 3H),0.91 (t, 2H, J=7.00Hz); 13C(CDCl3) delta 192.42, 181.81, 178.90, 172.87, 148.51, 144.87, 143.77,143.55, 135.10, 135.06, 132.62, 132.56, 126.73, 126.64, 126.57, 126.36, 67.71,67.29, 66.19, 48.82, 22.23, 14.91.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

59
[ 4497-71-6 ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.7%	With triethylamine; In toluene; at 50℃; for 3h;	To a suspensionof (19) (0.395, 1.50mmol) in 2mL oftoluene, pyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227g,2.25mmol) were added drop-wise and stirred at 50C for 3h. The toluene was thenremoved in vacuo. Reaction mixturewas filtered under vacuum suction, washed with distilled water and EtOH anddried to afford (52) as an orangesolid, 99.7%.1H (CDCl3) delta 8.65-8.57 (m,3H), 8.16 (dd, 1H, J=1.15,7.71Hz), 8.13 (dd, 1H, J=1.06, 7.70Hz),7.79 (dt, 1H, J=1.31, 7.57Hz),7.69 (dt, 1H, J=1.27, 7.55Hz),7.53 (br s, 1H), 4.76 (s, 2H), 3.17 (s, 3H), 1.96 (s, 3H); 13C (CDCl3)delta 182.05, 179.42, 172.59, 150.55, 144.07, 143.86, 143.80, 143.14, 135.33,132.78, 132.44, 130.23, 126.78, 45.81, 44.98, 21.82.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

60
[ 4497-72-7 ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-ethylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.9%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspensionof (19) (0.395, 1.50mmol) in 2mL oftoluene, pyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227g,2.25mmol) were added drop-wise and stirred at 50C for 3h. The toluene was thenremoved in vacuo. Reaction mixturewas filtered under vacuum suction, washed with distilled water and EtOH anddried to afford (52) as an orangesolid, 99.7%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

61
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-propylacetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-propylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.9%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspensionof (19) (0.395, 1.50mmol) in 2mL oftoluene, pyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227g,2.25mmol) were added drop-wise and stirred at 50C for 3h. The toluene was thenremoved in vacuo. Reaction mixturewas filtered under vacuum suction, washed with distilled water and EtOH anddried to afford (52) as an orangesolid, 99.7%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

62
[ 4531-59-3 ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-isopropylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.0%	With triethylamine; In toluene; at 50℃; for 3h;	To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.1H (CDCl3) delta 8.64 (s, 1H), 8.62 (d,1H, J=2.40Hz), 8.58 (d, 1H, J=2.30Hz), 8.17 (dd, 1H, J=0.80, 7.68Hz), 8.13 (dd, 1H, J=0.75, 7.77Hz), 7.80 (dt, 1H, J=1.26, 7.58Hz), 7.70 (dt, 1H, J=1.24, 7.55Hz), 7.49 (br s, 1H),4.90-4.72 (m, 2H), 4.65-4.55 (m, 1H), 1.96 (s, 3H), 1.33 (d, 3H, J=6.35Hz), 1.11 (d, 2H, J=6.93Hz); 13C (CDCl3)delta 171.97, 150.50, 144.07, 143.96, 143.75, 135.25, 132.70, 132.36, 130.40,126.84, 126.67, 77.20, 50.35, 45.15, 29.68, 23.33, 21.43, 19.94

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

63
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-cyclopropylacetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-cyclopropylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.9%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

64
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-butylacetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-butylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.5%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

65
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-isobutylacetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-isobutylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.5%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

66
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-cyclopentylacetamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-cyclopentylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.2%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

67
[ 4613-08-5 ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-benzylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.0%	With triethylamine; In toluene; at 50℃; for 3h;	General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56
[2]ChemMedChem,2016,p. 1944 - 1955

68
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-(2-methoxyethyl)propionamide [ No CAS ]
[ 20010-99-5 ]
N-{1,4-dioxo-3-[(pyrazin-2-ylmethyl)amino]-1,4-dihydronaphthalen-2-yl}-N-(2-methoxyethyl)propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.2%	With triethylamine; In toluene; at 50℃; for 3h;	To a suspension of (72) (1.415g, 4.4mmol) in 5mL of toluene, pyrazin-2-ylmethylamine(0.576g, 5.3mmol) and triethylamine (0.667g, 6.6mmol) were added drop-wise andstirred at 50C for 3h. The toluene was removed in vacuo. 25mL of distilled water was added and then extracted withEtOAc. The organic layer was washed with brine and dried over Na2SO4.Purification by column (92:8 EtOAC/MeOH) afforded (73) as an orange oil, 32.2%.1H (CDCl3) delta 8.60(s, 1H), 8.59 (d, 1H, J=2.13Hz), 8.54 (d, 1H, J=2.18Hz), 8.12 (d, 1H, J=7.54Hz),8.08 (d, 1H, J=7.55Hz), 7.76 (dt, 1H, J=1.03, 7.48Hz), 7.66 (dt, 1H, J=0.96, 7.55Hz), 7.50 (br s, 1H), 5.10-4.73 (m, 2H), 3.95-3.43 (m,4H), 3.17 (s, 3H), 2.28-2.12 (m, 2H), 1.05 (t, 3H, J=7.39Hz); 13C(CDCl3) delta 175.92, 143.81, 135.04, 132.60, 132.38, 130.56, 126.63,126.55, 69.87, 58.44, 48.82, 27.26, 9.12.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 104,p. 42 - 56

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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. 20010-99-5 ]

Quality Control of [ 20010-99-5 ]

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Calculated chemistry of [ 20010-99-5 ]

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Medicinal Chemistry

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[ 20010-99-5 ] Synthesis Path-Upstream 1~5

[ 20010-99-5 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 20010-99-5 ]

Amines

Related Parent Nucleus of [ 20010-99-5 ]

Pyrazines

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[ 20010-99-5 ]

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[ 20010-99-5 ]