[ CAS No. 41110-28-5 ] {[proInfo.proName]}

Name: 41110-28-5|3-Methylpyrazine-2-carboxylic acid|97%
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Quality Control of [ 41110-28-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 41110-28-5 ]

CAS No. :	41110-28-5	MDL No. :	MFCD08705765
Formula :	C₆H₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DEDJQZNLAXYJBT-UHFFFAOYSA-N
M.W :	138.12	Pubchem ID :	13153468
Synonyms :

Calculated chemistry of [ 41110-28-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.96
TPSA :	63.08 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) :	-7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.54
Log Po/w (XLOGP3) :	0.04
Log Po/w (WLOGP) :	0.48
Log Po/w (MLOGP) :	-0.88
Log Po/w (SILICOS-IT) :	0.7
Consensus Log Po/w :	0.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.1
Solubility :	11.0 mg/ml ; 0.0795 mol/l
Class :	Very soluble
Log S (Ali) :	-0.92
Solubility :	16.7 mg/ml ; 0.121 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.38
Solubility :	5.71 mg/ml ; 0.0413 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 41110-28-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 41110-28-5 ]

* 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 [ 41110-28-5 ]
Downstream synthetic route of [ 41110-28-5 ]

[ 41110-28-5 ] Synthesis Path-Upstream 1~5

1
[ 5910-89-4 ]
[ 41110-28-5 ]

Reference： [1] Journal of Organic Chemistry, 2002, vol. 67, # 2, p. 556 - 565
[2] International Journal of Molecular Sciences, 2018, vol. 19, # 10,

2
[ 67-56-1 ]
[ 41110-28-5 ]
[ 41110-29-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	at 80℃; for 5 h;	In a 2-E flask, 3-methylpyrazine-2-carboxylic acid (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mE). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mE, 506 mmol) was added over a time period of 5 mm. The reaction mixture was heated to 80° C. for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mE). The excess acid was neutralized careffilly with aqueous NaOH (SM, 200 mE). The aqueous layer was separated and extracted with DCM (250 mE). The combined organic layers were combined, dried over Mg504 and concentrated to afford the title compound (16.15 g, 106 mmol, 73percent). MS mlz=153 (M+H).
73%	With sulfuric acid In methanol at 80℃; for 5 h;	In a 2-L flask, 3-methylpyrazine-2-carboxylic acid (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and A-1813-WO-PCT - 148 - concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 °C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with of aqueous NaOH (5N or 5M, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgS0₄ and concentrated to afford 16.15 g of the title compound (106 mmol, 73percent). MS m/z=153 [M+H]⁺. Calculated for C₇H₈N₂0₂: 152
73%	at 80℃; for 5 h; Cooling with ice	In a 2-L flask, 3-methylpyrazine-2-carboxylic acid (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 °C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with of aqueous NaOH (5 M, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgSO₄ and concentrated to afford 16.15 g of methyl 3-methylpyrazine-2-carboxylate (265A, 106 mmol, 73percent). MS m/z=153 [M+H]⁺.

67%

for 5 h; Reflux

To a cooled suspension of 3-methylpyrazine-2-carboxylic acid (5.00 g, 36.2 mmol) in methanol (127 mL) was slowly added concentrated sulfuric acid (13.5 g, 7.34 mL, 127 mmol). The reaction mixture was heated to reflux for 5 h. After this time, LCMS analysis showed only a single peak, with a mass corresponding to the desired product. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in dichloromethane and washedwith excess aqueous 2N NaOH. The organic layer was kept and the aqueous re-extracted with a further 2 portions of dichloromethane. The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide the desired ester (3.7 g, 67 percent) as a yellow solid. The product was used without further purification in subsequent reactions.1H-NMR (400 MHz, CDCI3): ö = 8.63 (d, J=2.3 Hz, 1H), 8.53 (d, J=2.0 Hz, 1H), 4.02 (s, 3H), 2.87 (s, 3H).

Reference： [1] Patent: US2014/213581, 2014, A1, . Location in patent: Paragraph 0773; 0793
[2] Patent: WO2014/138484, 2014, A1, . Location in patent: Page/Page column 147; 148
[3] Patent: WO2016/22724, 2016, A1, . Location in patent: Page/Page column 292; 293
[4] Patent: WO2016/174073, 2016, A1, . Location in patent: Page/Page column 44
[5] Patent: WO2010/130970, 2010, A1, . Location in patent: Page/Page column 39-40
[6] Patent: US2015/38497, 2015, A1, . Location in patent: Paragraph 0981; 0982

3
[ 41110-28-5 ]
[ 41110-29-6 ]

Reference： [1] Patent: US2014/249104, 2014, A1, . Location in patent: Page/Page column

4
[ 41110-28-5 ]
[ 1166831-45-3 ]
[ 1262860-62-7 ]

Reference： [1] Patent: US2015/38497, 2015, A1,
[2] Patent: WO2016/22724, 2016, A1,

5
[ 41110-28-5 ]
[ 1166831-45-3 ]

Reference： [1] Patent: US2014/213581, 2014, A1,

[ 41110-28-5 ] Synthesis Path-Downstream 1~57

1
[ 15454-54-3 ]
[ 41110-28-5 ]
[ 111885-13-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 201 - 207

3
[ 5910-89-4 ]
[ 41110-28-5 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 556 - 565
[2]International Journal of Molecular Sciences,2018,vol. 19

4
[ 64-17-5 ]
[ 41110-28-5 ]
[ 25513-92-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	With hydrogenchloride; In ethanol; at 70℃; for 16h;	A solution of <strong>[41110-28-5]3-methylpyrazinecarboxylic acid</strong> (Vishweshar, J. Org. Chem. 2002, 67, 556) (3.2 mL, 30 mmol) in ethanol (20 mL) was saturated with hydrogen chloride and stirred at 70 C. for 16 hours. The solution was concentrated, the residue was taken up in chloroform and the solution was washed with 1 N sodium hydroxide and brine, dried over magnesium sulfate and concentrated to dryness, leaving a brown solid (828 mg, 66%)
		Example 1.1: Preparation of <strong>[41110-28-5]3-methyl-pyrazine-2-carboxylic acid</strong> ethyl esterTo a solution of <strong>[41110-28-5]3-methyl-pyrazine-2-carboxylic acid</strong> (10 g) (commercially available) and jV,7V-dimethylformamide ("DMF") (1 drop) in dichloromethane (20 ml) at ambient temperature was added drop wise oxalyl chloride (2.57 ml). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and the residue dissolved in dichloromethane (20 ml). Triethylamine (4.04 ml) was added to this solution followed by drop wise addition of ethanol (10 ml). The reaction mixture was stirred at ambient temperature for one hour and then concentrated. The residue was purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in zso-hexane) to give 3- methyl-pyrazine-2-carboxylic acid ethyl ester (9.85 g). MH+ = 167, RT = 0.73 min (Method A). IH-NMR (400 MHz, CDCl3): 8.61 (d, IH), 8.54 (d, IH), 4.49 (q, 2H), 2.85 (s, 3H), 1.46 (t, 3H) ppm.

Reference： [1]Patent: US2005/234065,2005,A1 .Location in patent: Page/Page column 27
[2]Patent: WO2010/130970,2010,A1 .Location in patent: Page/Page column 39

5
4,4-dimethyl-2,2-dioxo-2λ'-[1,2,3] oxathiazinane-3-carboxylic acid tert-butyl ester [ No CAS ]
[ 41110-28-5 ]
[ 207557-35-5 ]
(2S)-1-[1,1-Dimethyl-3-(5-methyl-3-pyrazin-2-yl-pyrazol-1-yl)-propylamino]-acetyl}-pyrrolidine-2-carbonitrile, Methanesulfonic Acid Salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	Example 93 (2S)-1-[1,1-Dimethyl-3-(5-methyl-3-pyrazin-2-yl-pyrazol-1-yl)-propylamino]-acetyl}-pyrrolidine-2-carbonitrile, Methanesulfonic Acid Salt This compound was made in analogy to example 83, steps A] to D] from methyl pyrazinecarboxylic acid, acetone, 4,4-dimethyl-2,2-dioxo-2lambda'-[1,2,3]oxathiazinane-3-carboxylic acid tert-butyl ester and IIA as a methanesulfonic acid addition salt. MS (ISP): 382.3 (MH+, free base).

Reference： [1]Patent: US2003/130281,2003,A1

6
[ 929884-19-5 ]
[ 41110-28-5 ]
[ 929884-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; N,N-dimethyl-formamide; for 20h;	Step 1: To the product of Preparation 1 (1.00 g, 4.4 mmol) in DMF (15 ml) add <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (0.73 g, 5.3 mmol), HOBt hydrate (0.71 g, 5.3 mmol), EDCl (10.1 g, 5.3 mmol), and N-methylmorpholine (0.58 ml, 5.3 mmol). Stir 20 h and concentrate to obtain the crude hydrazide.

Reference： [1]Patent: US2007/66620,2007,A1 .Location in patent: Page/Page column 8

7
[ 870786-86-0 ]
[ 41110-28-5 ]
N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-3-methylpyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In tetrahydrofuran; for 3h;Heating / reflux;	Example 4. Production of N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pheny}-3-methylpyrazine-2-carboxamide (compound No. 1-17) 3-Methylpyrazine-2-carboxylic acid (138 mg, 1 mmol), 3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (299 mg, 1 mmol), 2-chloro-1-methylpyridinium iodide (255 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml) and refluxed under heating for 3 hours. The reaction solution was diluted with ethyl acetate, followed by washing with water. The organic layer was dried over magnesium sulfate anhydride, and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 290 mg of the desired compound. Yield: 69% Property: Melting point 133 to 134C

Reference： [1]Patent: EP1757595,2007,A1 .Location in patent: Page/Page column 22

8
[ 67-56-1 ]
[ 41110-28-5 ]
[ 41110-29-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sulfuric acid; at 80℃; for 5h;	In a 2-E flask, <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mE). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mE, 506 mmol) was added over a time period of 5 mm. The reaction mixture was heated to 80 C. for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mE). The excess acid was neutralized careffilly with aqueous NaOH (SM, 200 mE). The aqueous layer was separated and extracted with DCM (250 mE). The combined organic layers were combined, dried over Mg504 and concentrated to afford the title compound (16.15 g, 106 mmol, 73%). MS mlz=153 (M+H).
73%	With sulfuric acid; In methanol; at 80℃; for 5h;	In a 2-L flask, <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and A-1813-WO-PCT - 148 - concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with of aqueous NaOH (5N or 5M, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgS04 and concentrated to afford 16.15 g of the title compound (106 mmol, 73%). MS m/z=153 [M+H]+. Calculated for C7H8N202: 152
73%	With sulfuric acid; at 80℃; for 5h;Cooling with ice;	In a 2-L flask, <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with of aqueous NaOH (5 M, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgSO4 and concentrated to afford 16.15 g of methyl 3-methylpyrazine-2-carboxylate (265A, 106 mmol, 73%). MS m/z=153 [M+H]+.

70.9%	With thionyl chloride; at 0 - 60℃;	To a stirred solution of MeOH (50 mL) was added SOCl 2 (8.6 g, 72.4 mmol) dropwise at 0. Then <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (5 g, 36.2 mmol) was added to the reaction. The mixture was stirred at 60 overnight. The mixture was concentrated under reduced pressure and the residue was dissolved into EtOAc (50mL) . The organic phase was washed with saturated aq. NaHCO 3 (50 mL) . The organic phase was washed with brine, dried over Na 2SO 4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluted with: EtOAc/PE=1/1) to afford the title compound as yellow solid (3.9g, yield: 70.9%) . MS: M/e 153 (M+1) +.
70.9%	With thionyl chloride; at 0 - 60℃;	To a stirred solution of MeOH (50 mL) was added SOCl2(8.6 g, 72.4 mmol) dropwise at 0C. Then <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (5 g, 36.2 mmol) was added to the reaction. The mixture was stirred at 60 C overnight. The mixture was concentrated under reduced pressure and the residue was dissolved into EA (50mL) . The organic phase was washed with saturated aq.NaHCO3(50 mL) . The organic phase was washed with brine, dried over Na2SO4and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluted with: EA/PE = 1/1) to afford the title compound as yellow solid (3.9g, yield: 70.9%) . MS: M/e 153 (M+1)+.
67%	With sulfuric acid; for 5h;Reflux;	To a cooled suspension of <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (5.00 g, 36.2 mmol) in methanol (127 mL) was slowly added concentrated sulfuric acid (13.5 g, 7.34 mL, 127 mmol). The reaction mixture was heated to reflux for 5 h. After this time, LCMS analysis showed only a single peak, with a mass corresponding to the desired product. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in dichloromethane and washedwith excess aqueous 2N NaOH. The organic layer was kept and the aqueous re-extracted with a further 2 portions of dichloromethane. The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide the desired ester (3.7 g, 67 %) as a yellow solid. The product was used without further purification in subsequent reactions.1H-NMR (400 MHz, CDCI3): oe = 8.63 (d, J=2.3 Hz, 1H), 8.53 (d, J=2.0 Hz, 1H), 4.02 (s, 3H), 2.87 (s, 3H).
	With diazomethyl-trimethyl-silane; In diethyl ether; toluene; at 20℃;	Example 1.2: Preparation of 3 -methyl -pyrazine-2-carboxylic acid methyl estermethanol(CH3)3SiCHN2 To a solution of <strong>[41110-28-5]3-methyl-pyrazine-2-carboxylic acid</strong> (4.7 g) in toluene (70 ml) and methanol (30 ml) at ambient temperature was added drop wise (trimethylsilyl)diazomethane (2M in diethyl ether) (26 ml). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and purified by passing through a pad of silica and eluting with 30% v/v ethyl acetate in wo-hexane to give <strong>[41110-28-5]3-methyl-pyrazine-2-carboxylic acid</strong> methyl ester (3.10 g). IH-NMR (400 MHz, CDCl3): 8.63 (d, IH), 8.53 (d, IH), 4.02 (s, 3H), 2.87 (s, 3H) ppm.
	With sulfuric acid; at 60℃; for 4h;	A solution of <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (10 g, 72.4 mmol) in MeOH (80 mL) and sulfuric acid, 95% (5 mL, 90 mmol) was heated to 60 C. for 4 hours. The solution was concentrated to remove MeOH, the residue dissolved in 50 mL of water and neutralized with 10% aq Na2CO3 solution to pH 12. The resulting solution was extracted with ethyl acetate (2×). The combine organic was dried and concentrated to give crude product methyl 3-methylpyrazine-2-carboxylate (9.1 g, 59.8 mmol, 83% yield). It was used for next step without further purification. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 8.63 (1H, s), 8.53 (1H, s), 4.02 (3H, s), 2.87 (3H, s). MS m/z=153 [M+H]+. Calculated for C7H8N2O2: 152.0.

Reference： [1]Patent: US2014/213581,2014,A1 .Location in patent: Paragraph 0773; 0793
[2]Patent: WO2014/138484,2014,A1 .Location in patent: Page/Page column 147; 148
[3]Patent: WO2016/22724,2016,A1 .Location in patent: Page/Page column 292; 293
[4]Patent: WO2019/196803,2019,A1 .Location in patent: Paragraph 0380; 0382
[5]Patent: WO2020/20097,2020,A1 .Location in patent: Paragraph 0763-0765
[6]Patent: WO2016/174073,2016,A1 .Location in patent: Page/Page column 44
[7]Patent: WO2010/130970,2010,A1 .Location in patent: Page/Page column 39-40
[8]Patent: US2015/38497,2015,A1 .Location in patent: Paragraph 0981; 0982
[9]Patent: WO2020/1448,2020,A1 .Location in patent: Page/Page column 39; 252

9
[ 41110-28-5 ]
[ 41110-29-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sulfuric acid;	Step 1: Methyl 3-methylpyrazine-2-carboxylate In a 2-L flask, <strong>[41110-28-5]3-methylpyrazine-2-carboxylic acid</strong> (Matrix, 19.95 g, 144 mmol) was suspended in MeOH (500 mL). The suspension was cooled in an ice-water bath, and concentrated sulfuric acid (Fluka, 27.3 mL, 506 mmol) was added over a time period of 5 min. The reaction mixture was heated to 80 C. for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in DCM (750 mL). The excess acid was neutralized carefully with aqueous NaOH (5m, 200 mL). The aqueous layer was separated and extracted with DCM (250 mL). The combined organic layers were combined, dried over MgSO4 and concentrated to afford 16.15 g of the title compound (106 mmol, 73%). MS m/z=153 [M+H]+. Calculated for C7H8N2O2: 152.

Reference： [1]Patent: US2014/249104,2014,A1 .Location in patent: Page/Page column

10
[ 41110-28-5 ]
[ 1620981-13-6 ]

Reference： [1]Patent: US2014/213581,2014,A1

11
[ 41110-28-5 ]
[ 1262860-61-6 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2014/213581,2014,A1
[3]Patent: US2014/249104,2014,A1
[4]Patent: WO2014/138484,2014,A1
[5]Patent: WO2016/22724,2016,A1

12
[ 41110-28-5 ]
[ 1166831-45-3 ]

Reference： [1]Patent: US2014/213581,2014,A1

13
[ 41110-28-5 ]
[ 1620981-14-7 ]

Reference： [1]Patent: US2014/213581,2014,A1

14
[ 41110-28-5 ]
[ 1620981-15-8 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2015/38497,2015,A1

15
[ 41110-28-5 ]
[ 1651201-80-7 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2015/38497,2015,A1

16
[ 41110-28-5 ]
[ 1262860-63-8 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: WO2014/138484,2014,A1
[3]Patent: US2015/38497,2015,A1

17
[ 41110-28-5 ]
[ 1262860-60-5 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2014/249104,2014,A1
[3]Patent: WO2014/138484,2014,A1
[4]Patent: US2015/38497,2015,A1
[5]Patent: WO2016/22724,2016,A1
[6]Patent: WO2016/22724,2016,A1
[7]Patent: WO2016/22724,2016,A1

18
[ 41110-28-5 ]
[ 1262860-62-7 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2014/213581,2014,A1
[3]Patent: US2014/213581,2014,A1
[4]Patent: US2014/249104,2014,A1
[5]Patent: WO2014/138484,2014,A1
[6]Patent: WO2016/22724,2016,A1
[7]Patent: WO2016/22724,2016,A1
[8]Patent: WO2020/1448,2020,A1

19
[ 41110-28-5 ]
[ 1620981-17-0 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2014/213581,2014,A1
[3]Patent: US2014/213581,2014,A1
[4]Patent: US2014/249104,2014,A1

20
[ 41110-28-5 ]
[ 1620981-20-5 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2014/213581,2014,A1
[3]Patent: US2014/213581,2014,A1

21
[ 41110-28-5 ]
[ 1620981-19-2 ]

Reference： [1]Patent: US2014/213581,2014,A1
[2]Patent: US2014/213581,2014,A1
[3]Patent: US2014/213581,2014,A1

22
[ 41110-28-5 ]
[ 1624604-96-1 ]