[ CAS No. 69816-38-2 ] {[proInfo.proName]}

Name: 69816-38-2|5-(Trifluoromethyl)pyrazin-2-amine|97%
Brand: Ambeed
SKU: A224749
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Quality Control of [ 69816-38-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 69816-38-2 ]

CAS No. :	69816-38-2	MDL No. :	MFCD10697797
Formula :	C₅H₄F₃N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILDRNIDSVAZBMZ-UHFFFAOYSA-N
M.W :	163.10	Pubchem ID :	13341115
Synonyms :

Calculated chemistry of [ 69816-38-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.44
TPSA :	51.8 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.96
Log Po/w (XLOGP3) :	0.35
Log Po/w (WLOGP) :	2.24
Log Po/w (MLOGP) :	0.11
Log Po/w (SILICOS-IT) :	1.25
Consensus Log Po/w :	0.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.41
Solubility :	6.35 mg/ml ; 0.039 mol/l
Class :	Very soluble
Log S (Ali) :	-1.0
Solubility :	16.2 mg/ml ; 0.0995 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.17
Solubility :	1.1 mg/ml ; 0.00676 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 69816-38-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 69816-38-2 ]

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

Upstream synthesis route of [ 69816-38-2 ]
Downstream synthetic route of [ 69816-38-2 ]

[ 69816-38-2 ] Synthesis Path-Upstream 1~4

1
[ 799557-87-2 ]
[ 69816-38-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 80℃; for 3.5 h; Sealed tube	2-Chloro-5-(trifluoromethyl)pyrazine (5.0 g, 27 mmol) (Oakwood Products, 075803) was stirred in ammonium hydroxide (190 mL, 2.7 mol) and heated to 80° C. for 3.5 h in a sealed pressure vessel. After cooling to rt, the aqueous mixture was extracted with DCM (4*). The extracts were combined, dried over sodium sulfate, filtered, and concentrated to afford the title compound as a white solid (4.0 g, 90percent). ¹H NMR (400 MHz, CDCl₃) δ 8.34 (s, 1H), 8.01 (s, 1H), 5.01 (br s, 2H). LCMS for C₅H₅F₃N₃ (M+H)⁺: calculated m/z=164.0; found 164.1.

Reference： [1] Patent: US2018/9816, 2018, A1, . Location in patent: Paragraph 1377; 1378

2
[ 1672-50-0 ]
[ 431-67-4 ]
[ 69816-38-2 ]

Yield	Reaction Conditions	Operation in experiment
15%	Stage #1: at 0 - 20℃; Stage #2: at 135℃; for 8 h;	Step A: 5-(Trifluoromethyl)pyrazin-2-amine To an ice bath-cooled solution of 5,6-diaminopyrimidin-4-ol (18 g, 143 mmol) in 3M sodium hydroxide (180 mL, 540 mmol), was added 3,3-dibromo-1,1,1-trifluoropropan-2-one (25.2 g, 93 mmol). The reaction was stirred for 3 days at ambient temperature. The solids were filtered, dissolved in 60percent sulfuric acid (140 mL), and stirred at 135° C. for 8 h. The reaction was cooled, poured over ice and allowed to sit for 16 hours. The solution was neutralized to pH 8 with conc. ammonium hydroxide and extracted with ethyl acetate (5.x.100 mL), dried over sodium sulfate, filtered and concentrated. The solid residue was recrystallized from benzene/hexane to afford 5-(trifluoromethyl)pyrazin-2-amine (2.28 g, 14 mmol, 15percent yield). ¹H NMR (400 MHz, CDCl₃) δ ppm 8.32 (1H, s), 7.99 (1H, d, J=1.26 Hz), 5.02 (2H, br. s.). MS (LC/MS) R.T.=1.56; [M+H]⁺=164.03.
15%	Stage #1: at 20℃; for 72 h; Stage #2: With sulfuric acid In water at 135℃; for 8 h; Stage #3: With ammonium hydroxide In water	Step A: 5-(trifluoromethyl)pyrazin-2-amine To an ice bath-cooled solution of 5,6-diaminopyrimidin-4-ol (18 g, 143 mmol) in 3M sodium hydroxide (180 mL, 540 mmol), was added 3,3-dibromo-l, l,l- trifluoropropan-2-one (25.2 g, 93 mmol). The reaction was stirred for 3 days at ambient temperature. The solids were filtered, dissolved in 60percent sulfuric acid (140 mL), and stirred at 135 °C for 8 h. The reaction was cooled, poured over ice and allowed to sit for 16 hours. The solution was neutralized to pH 8 with cone, ammonium hydroxide and extracted with ethyl acetate (5 X 100 mL), dried over sodium sulfate, filtered and concentrated. The solid residue was recrystallized from benzene/hexane to afford 5-(trifluoromethyl)pyrazin-2-amine (2.28 g, 14 mmol, 15 percent yield). 3/4 NMR (400 MHz, CDCl₃) δ ppm 8.32 (1 H, s), 7.99 (1 H, d, J=1.26 Hz), 5.02 (2 H, br. s.). MS (LC/MS) R.T. = 1.56; [M+H]⁺ = 164.03.

Reference： [1] Patent: US2009/270405, 2009, A1, . Location in patent: Page/Page column 82
[2] Patent: WO2011/53292, 2011, A1, . Location in patent: Page/Page column 132

3
[ 431-67-4 ]
[ 69816-38-2 ]

Reference： [1] Patent: US4293552, 1981, A,

4
[ 69816-38-2 ]
[ 1196152-38-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 12, p. 4603 - 4614

[ 69816-38-2 ] Synthesis Path-Downstream 1~72

2
[ 69816-38-2 ]
[ 134510-03-5 ]

Yield	Reaction Conditions	Operation in experiment
		Description 37 2-CHLORO-5- (TRIFLUOROMETHYL) pyrazine (D37) 2-Amino-5-trifluoromethylpyrazine (Miesel, US 4 293 552) was converted into 5- TRIFLUOROMETHYLPYRAZIN-2-ONE (Fitzjohn, EP 408196). 5-Trifluoromethylpyrazin-2-one (0.5g) was heated at reflux in POCI3 (3ml) containing 1 drop of conc. H2SO4 for 3h. The cooled mixture was poured onto ice and brought to pH 5 by addition of solid NAHCO3 and extracted (3x) with diethyl ether. The ethereal extracts were washed with water and brine, dried (Na2SO4) and evaporated to give the title compound (D37) as a light yellow oil (0. 2G) which was sufficiently pure for use without further purification.'H NMR 8 [CDCI3] : 8.76 (1 H, s), 8.72 (1H, s).
	With sulfuric acid; sodium nitrite; at 0℃; for 0.75h;Cooling with ice;	Intermediate (1 h): 5-(trifluoromethyl)pyrazin-2(1H)-one; Concentrated sulfuric acid (2.38 mL) was stirred in an ice bath. Sodium nitrite (199 mg) was added in one portion, and the mixture was stirred for 5 minutes and allowed to warm to room temperature over 5 minutes. It was then heated to 40 C. for 10 minutes and then cooled 0 C. A solution of <strong>[69816-38-2]5-(trifluoromethyl)-pyrazin-2-amine</strong> (313 mg) in 3.4 mL concentrated sulfuric acid was added drop-wise over 5 minutes. The reaction was allowed to stir in the ice bath for 10 minutes, then at room temperature for 10 minutes, then at 40 C. for 20 minutes. The reaction was then pipetted into stirring ice water. The aqueous layer was extracted twice with ethyl acetate, which was then washed with water and brine and dried over MgSO4. Purification by flash column chromatography (40 g, 0-100% ethyl acetate in heptanes) gave 0.239 g of Intermediate (1 h) as a white solid. MS 163.1 (M-1, APCI-).

Reference： [1]Patent: WO2005/14571,2005,A1 .Location in patent: Page/Page column 26
[2]Patent: US2010/184777,2010,A1 .Location in patent: Page/Page column 13

3
[ 832692-80-5 ]
[ 69816-38-2 ]
7-(3-methylpyridin-2-yl)-N-(5-(trifluoromethyl)pyrazin-2-yl)-[1,8]naphthyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 20h;	Heat a mixture of 5-chloro-2- (3-methylpyridin-2-yl)- [1, 8] naphthyridine (51 mg, 0.2 MMOL), 2-AMINO-5-TRIFLUOROMETHYLPYRAZINE (42.0 mg, 0. 25 MMOL), xantphos (11.6 mg, 0.02 mmol), Pd2 (dba) 3 (18.3 mg, 0.02 mmol) and Cs2CO3 (130 mg, 0.4 mmol) in dioxane (2.0 mL) at 100C for 20 HOURS. COOL the mixture, concentrate under vacuum, dilute with EtOAc/ water (5.0 mL each), filter through celite, wash celite with EtOAc (2 x 5 mL) and dry the combined organic layers with MGS04. Filter the dried extract and concentrate under vacuum to afford the crude product. Purify by preparative TLC using 2% MEOH/ETOAC as eluent to afford the title compound as a yellow SOLID. H NMR (400 MHZ, DMSO-D6) 8 10.6 (s, 1H), 9.04 (d, 1H, J=2.1 Hz), 9.0 (s, LH), 8.77 (s, 2H), 8.59 (d, 1H, J=1.6 Hz), 8.4 (s, 1H), 8.20 (d, 1H, J=2. 2 Hz), 7. 81 (d, IH, J=L. 9 Hz), 7.42 (dd, 1H), 2.65 (s, 3H). MS = 383. 11 (M+H).

Reference： [1]Patent: WO2005/7652,2005,A2 .Location in patent: Page/Page column 41; 88-89

4
3-[2-(4-nitro-phenoxycarbonylamino)-4-trifluoromethyl-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 69816-38-2 ]
3-{4-trifluoromethyl-2-[3-(5-trifluoromethyl-pyrazin-2-yl)-ureido]-phenoxymethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 20 - 85℃;	Step 2: 3-{4-Trifluoromethyl-2-[3-(5-tri-fluoromethyl-pyrazin-2-yl)-ureido]-phenoxymethyl}-piper-idine-1-carboxylic acid tert-butyl ester. 3-[2-(4-Nitro-phenoxycarbonylamino) -4-trifluoromethyl-phenoxymethyl] -piperidine-1-carboxylic acid tert-butyl ester (217 mg, 0.4 mmol) and <strong>[69816-38-2]5-trifluoromethyl-pyrazin-2-ylamine</strong> (66 mg, 0.4 mmol) (prepared according to the method of U.S. 4,293,552) were mixed as solids in a 5 mL reaction vial, diluted with 400 uL NMP, capped and stirred as a darkyellow solution that then was immersed in an oil bath at 85C and stirred for six hours. The reaction mixture was cooled to room temperature and stirred overnight. NMP then was removed by Kugelrohr distillation at 0.5 mm and 80C. The brown residue was diluted to 30 mL with CH2C12 then washed 3 x 30 mL with 1M Na2C03 to remove p-nitro-phenol. The organics were dried (MgS04) , filtered, and concentrated to a crude solid that was triturated with EtOAc and filtered to give the desired product as a white solid.

Reference： [1]Patent: WO2006/21002,2006,A2 .Location in patent: Page/Page column 49-50

5
[ 884004-45-9 ]
[ 69816-38-2 ]
5-trifluoromethyl-6-[8-(5-trifluoromethyl-pyrazin-2-ylamino)-pyrido[2,3-b]pyrazin-3-yl]-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 140℃; for 20h;Product distribution / selectivity;	L. 5-(Trifluoromethyl)-6-(8-(5-(trifluoromethyl)pyrazin-2-ylarnino)pyrido[2,3-blpyrazin-3- vDnicotinamide (compound 15) Heat a mixture of 6-(8-chloropyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide (70.6 mg, 0.2 mmol) and <strong>[69816-38-2]2-amino-5-trifluoromethyl-pyrazine</strong> (98.4 mg, 0.6 mmol) in a screw cap vial at 1400C for 20 hours under N2 atmosphere. Purify the reaction mixture by column chromatography using EtOAc to 1% MeOH / EtOAc as eluent to afford the title compound as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 11.182 (s, IH), 9.456 (s, IH), 9.44(s, IH), 9.074 (d, IH, J=I.3 Hz), 9.052 (s, IH), 8.87(d, IH, J=1.3 Hz), 8.828 (d, IH, J=2.6 Hz), 8.542 (s, IH), 7.974 (1, IH). MS = 481.42 (M+H). The IC50 determined as described in Example 6 is less than 1 micromolar.

Reference： [1]Patent: WO2006/42289,2006,A2 .Location in patent: Page/Page column 65

6
concentrated aqueous ammonium hydroxide [ No CAS ]
4,5-Diamino-6-hydroxypyrimidine sulphate [ No CAS ]
[ 431-67-4 ]
[ 69816-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	In sulfuric acid;	Preparation 30 2-Amino-5-trifluoromethylpyrazine A solution of 18 g. of 4,5-diamino-6-hydroxypyrimidine sulfate (commercially available) in 180 ml. of aqueous 3 N sodium hydroxide was prepared and cooled, and to the cooled mixture there was added 25.2 g. of 3,3-dibromo-1,1,1-trifluoropropanone. The reaction mixture was stirred for about 48 hours at room temperature. The precipitate which formed was filtered off, dissolved in 140 ml. of aqueous 60% sulfuric acid, and heated at about 135 C. for about 8 hours. The reaction mixture was poured over crushed ice and the aqueous mixture neutralized using concentrated aqueous ammonium hydroxide. The solution was then extracted with ethyl acetate. The ethyl acetate extracts were concentrated in vacuo to dryness and the residue recrystallized from a mixture of benzene and hexane to yield product weighing 2.2 g., and having a melting point of about 118-122 C. The product was identified by NMR spectrum and elemental analyses as 2-amino-5-trifluoromethylpyrazine. Analyses calcd. for C5 H4 F3 N3:

Reference： [1]Patent: US4293552,1981,A

7
[ 4461-34-1 ]
[ 69816-38-2 ]
1-(2-Chlorobenzyl)-3-(5-trifluoromethyl-2-pyrazinyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1A. 1-(2-Chlorobenzyl)-3-(5-trifluoromethyl-2-pyrazinyl)urea, having a melting point of about 219-220 C., from 500 mg. of 2-amino-5-trifluoromethylpyrazine and 600 mg. of 2-chlorobenzoylisocyanate.

Reference： [1]Patent: US4293552,1981,A

8
[ 4461-34-1 ]
[ 62632-15-9 ]
[ 69816-44-0 ]
[ 69816-38-2 ]
1-(2-Bromobenzoyl)-3-(5-trifluoromethyl-2-pyrazinyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1K. 1-(2-Bromobenzoyl)-3-(5-trifluoromethyl-2-pyrazinyl)urea, having a melting point of about 206-208 C., from 300 mg. of 2-amino-5-trifluoromethylpyrazine and 500 mg. of 2-bromobenzoylisocyanate. 1L. 1-(2-Chlorobenzoyl)-3-[5-(4-bromophenyl)-6-chloro-2-pyrazinyl]urea, weighing 1.4 g., and having a melting point of about 240-242 C., from 0.9 g. of 2-amino-5-(4-bromophenyl)-6-chloropyrazine and 0.65 g. of 2-chlorobenzoylisocyanate.

Reference： [1]Patent: US4293552,1981,A

9
[ 1160608-75-2 ]
[ 69816-38-2 ]
[ 1160608-05-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; In toluene; at 20 - 90℃; for 18h;	Example 93[2-(2,6-Dichloro-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-(5-trifluoromethyl-pyrazin-2-yl)-amine To a mixture of 7-chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine (113 mg, 0.34 mmol), 1,2,3,4,5-pentaphenyl-1-(di-t-butylphosphino)ferrocene (49 mg, 0.07 mmol), tris(dibenzylideneacetone)dipalladium (0) (31 mg, 0.03 mmol), and <strong>[69816-38-2]5-trifluoromethyl-pyrazin-2-ylamine</strong> (66 mg, 0.41 mmol) in toluene (3 mL) was added NaOtBu (40 mg, 0.41 mmol) at rt. The mixture was heated to 90 C. under N2. After 18 h, the reaction mixture was cooled and filtered through a pad of diatomaceous earth, eluting with MeOH (30 mL). The filtrate was concentrated and the crude residue was purified using preparative reverse-phase HPLC to afford the title compound a colorless solid (43 mg, 28%). MS (ESI): mass calcd. for C17H9Cl2F3N6S, 455.9; m/z found, 457.0 [M+H]+. 1H NMR ((CD3)2SO): 10.77 (s, 1H), 9.49 (s, 1H), 8.88-8.87 (m, 1H), 8.75 (s, 1H), 7.59 (d, J=8.0 Hz, 2H), 7.45 (dd, J=8.5, 7.7 Hz, 1H), 4.83 (s, 2H).

Reference： [1]Patent: US2009/156599,2009,A1 .Location in patent: Page/Page column 37

10
[ 1672-50-0 ]
[ 431-67-4 ]
[ 69816-38-2 ]

Yield	Reaction Conditions	Operation in experiment
15%		Step A: 5-(Trifluoromethyl)pyrazin-2-amine To an ice bath-cooled solution of <strong>[1672-50-0]5,6-diaminopyrimidin-4-ol</strong> (18 g, 143 mmol) in 3M sodium hydroxide (180 mL, 540 mmol), was added 3,3-dibromo-1,1,1-trifluoropropan-2-one (25.2 g, 93 mmol). The reaction was stirred for 3 days at ambient temperature. The solids were filtered, dissolved in 60% sulfuric acid (140 mL), and stirred at 135 C. for 8 h. The reaction was cooled, poured over ice and allowed to sit for 16 hours. The solution was neutralized to pH 8 with conc. ammonium hydroxide and extracted with ethyl acetate (5×100 mL), dried over sodium sulfate, filtered and concentrated. The solid residue was recrystallized from benzene/hexane to afford 5-(trifluoromethyl)pyrazin-2-amine (2.28 g, 14 mmol, 15% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.32 (1H, s), 7.99 (1H, d, J=1.26 Hz), 5.02 (2H, br. s.). MS (LC/MS) R.T.=1.56; [M+H]+=164.03.
15%		Step A: 5-(trifluoromethyl)pyrazin-2-amine To an ice bath-cooled solution of <strong>[1672-50-0]5,6-diaminopyrimidin-4-ol</strong> (18 g, 143 mmol) in 3M sodium hydroxide (180 mL, 540 mmol), was added 3,3-dibromo-l, l,l- trifluoropropan-2-one (25.2 g, 93 mmol). The reaction was stirred for 3 days at ambient temperature. The solids were filtered, dissolved in 60% sulfuric acid (140 mL), and stirred at 135 C for 8 h. The reaction was cooled, poured over ice and allowed to sit for 16 hours. The solution was neutralized to pH 8 with cone, ammonium hydroxide and extracted with ethyl acetate (5 X 100 mL), dried over sodium sulfate, filtered and concentrated. The solid residue was recrystallized from benzene/hexane to afford 5-(trifluoromethyl)pyrazin-2-amine (2.28 g, 14 mmol, 15 % yield). ¾ NMR (400 MHz, CDCl3) delta ppm 8.32 (1 H, s), 7.99 (1 H, d, J=1.26 Hz), 5.02 (2 H, br. s.). MS (LC/MS) R.T. = 1.56; [M+H]+ = 164.03.

Reference： [1]Patent: US2009/270405,2009,A1 .Location in patent: Page/Page column 82
[2]Patent: WO2011/53292,2011,A1 .Location in patent: Page/Page column 132

11
[ 69816-38-2 ]
[ 1196152-38-1 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4603 - 4614

12
[ 1220632-30-3 ]
[ 69816-38-2 ]
N-[5-(trifluoromethyl)pyrazin-2-yl]-7-[3-(trifluoromethyl)pyridin-2-yl]-1,8-naphthyridin-4-annine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4359 - 4363

13
4-Chloro-2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine [ No CAS ]
[ 69816-38-2 ]
Example 192 [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7137 - 7141

14
4-chloro-2-isopropyl-7-(3-trifluoromethylpyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine [ No CAS ]
[ 69816-38-2 ]
[2-Isopropyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(5-trifluoromethyl-pyrazin-2-yl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7137 - 7141

15
[ 1178884-53-1 ]
[ 69816-38-2 ]
[ 1360055-12-4 ]

Reference： [1]Patent: US2012/40949,2012,A1

16
[ 1178884-53-1 ]
[ 69816-38-2 ]
[ 1360056-16-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere;	Example 11 To a solution of <strong>[69816-38-2]5-(trifluoromethyl)pyrazin-2-amine</strong> (146 mg, 0.90 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (200 mg, 0.90 mmol), cesium carbonate (1.02 g, 3.13 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthine (77.7 mg, 0.13 mmol) in dioxane (10.0 ml) was added tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) and the reaction mixture purged with argon (3) before being warmed to 90 C. for 18 hr. The mixture was cooled, diluted with dichloromethane and water (50 mL) and the layers separated. The aqueous phase was extracted with methylene chloride (225 mL). The organic phases were combined and dried over MgSO4. The mixture was filtered and evaporated and the residue purified via automated flash chromatography (Analogix, SF15-24 g column, 1%-10% methanol/dichloromethane gradient) to give 6-chloro-2-methyl-4-(5-trifluoromethyl-pyrazin-2-ylamino)-2H-pyridazin-3-one (197 mg, 72%) as a yellow solid: LC/MS m/e calculated for C10H7ClF3N5O [M]+305.03, observed 305.9

Reference： [1]Patent: US2012/40949,2012,A1 .Location in patent: Page/Page column 65

17
[ 70-23-5 ]
[ 69816-38-2 ]
6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; at 80℃; for 16h;	To a stirred solution of compound 1 (500 mg, 3.06 mmol) in EtOH (15 mL) was added ethyl bromopyruvate (0.77 mL, 6.13 mmol) at room temperature. The resulting mixture was heated to 80 C for 16 h. The reaction mixture was cooled to ambient temperature and concentrated. The residue was suspended in diethyl ether and the resulting solid was filtered and dried under vacuum to give the ester compound 2 as a yellow solid (524 mg, 66%).
	In 1,2-dimethoxyethane; at 60℃; for 72h;	Preparation of N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[l ,2- a]pyrazine-2-carboxamide (compound 1)Step A: Preparation of 6-(trifluoromethyl)imidazo[l,2-a]pyrazine-2-carboxylic acid ethyl esterTo a solution of <strong>[69816-38-2]2-amino-5-(trifluoromethyl)pyrazine</strong> (500 mg, 3.07 mmol) in 1,2- dimethoxyethane (10 mL) was added dropwise ethyl bromopyruvate (0.5 mL, 4.0 mmol). The reaction mixture was warmed to 60 C for 72 hours. The reaction mixture was then cooled to room temperature, and water was added (10 mL) to precipitate a solid. The suspension was stirred for 10 minutes, filtered, and the isolated solid was washed with water to afford the desired ester which was used in the next step without further drying. ¾ NMR (CDC13) delta 9.22 (s, 1H), 8.59 (s, 1H), 8.39 (s, 1H), 4.50 (q, 2H), 1.47 (t, 3H).

Reference： [1]Patent: WO2018/211323,2018,A1 .Location in patent: Page/Page column 00224
[2]Patent: WO2012/54233,2012,A1 .Location in patent: Page/Page column 40

18
[ 32315-10-9 ]
(4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine [ No CAS ]
[ 69816-38-2 ]
(4S)-7-(2-methylpyridin-4-yl)-N-(5-(trifluoromethyl)pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		To a stirred solution of <strong>[69816-38-2]5-(trifluoromethyl)pyrazin-2-amine</strong> (1164 mg, 7.13 mmol) in THF (10 mL) were added triethylamine (1.989 mL, 14.27 mmol) and triphosgene (706 mg, 2.378 mmol) at 25 C. and stirred for 1 h. Then (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine (600 mg, 2.378 mmol) was added and heated at 100 C. for 15 h in sealed tube. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with water (20 mL×2), brine (10 mL), dried over anhydrous Na2SO4 and concentrated under pressure to obtain the crude product. The crude product was purified by flash column chromatography (silica-gel: 100-200 mesh, eluent: 2% MeOH in DCM) to afford (4S)-7-(2-methylpyridin-4-yl)-N-(5-(trifluoromethyl)pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (125 mg, 0.283 mmol, 32% yield) as an off white solid (TLC: Eluent: 5% methanol in DCM, Rf: 0.3), LCMS (m/z): 442.24 [M+H]+. 1H-NMR (CDCl3, 400 MHz): 14.1 (s, 1H), 9.7 (s, 1H), 8.66-8.62 (m, 2H), 8.0 (s, 1H), 7.69-7.64 (m, 2H), 7.5 (d, J=8 Hz, 1H), 5.74-5.69 (m, 1H), 3.34-3.16 (m, 3H), 3.08-3.02 (m, 1H), 2.75 (s, 3H), 2.32-2.42 (m, 1H), 2.14-2.06 (m, 1H).
32%		To a stirred solution of <strong>[69816-38-2]5-(trifluoromethyl)pyrazin-2-amine</strong> (1 164 mg, 7.13 mmol) in THF (10 mL) were added triethylamine (1.989 mL, 14.27 mmol) and triphosgene (706 mg, 2.378 mmol) at 25 C and stirred for lh. Then (45)-7-(2-methylpyridin-4-yl)-2,3,4,5- tetrahydro-l,4-methanopyrido[2,3-£][l,4]diazepine (600 mg, 2.378 mmol) was added and heated at 100 C for 15 h in sealed tube. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (2x50 mL). The combined organic layer was washed with water (20 mLx2), brine (10 mL), dried over anhydrous Na2SC"4 and concentrated under pressure to obtain the crude product. The crude product was purified by flash column chromatography (silica-gel: 100-200 mesh, eluent: 2% MeOH in DCM) to afford (4,S)-7-(2-methylpyridin-4-yl)-N-(5-(trifluoromethyl)pyrazin-2-yl)-3,4-dihydro-l,4- methanopyrido[2,3-£][l,4]diazepine-5(2H)-carboxamide (125 mg, 0.283 mmol, 32% yield) as an off white solid (TLC: Eluent: 5% methanol in DCM, Rf. 0.3), LCMS (m/z): 442.24 [M+H]+.1H-NMR (CDC13, 400 MHz): 14.1 (s, 1H), 9.7 (s, 1H), 8.66-8.62 (m, 2H), 8.0 (s, 1H), 7.69-7.64 (m, 2H), 7.5 (d, J= 8 Hz, 1H), 5.74-5.69 (m, 1H), 3.34-3.16 (m, 3H), 3.08-3.02 (m, 1H), 2.75 (s, 3H), 2.32-2.42 (m, 1H), 2.14-2.06 (m, 1H).

Reference： [1]Patent: US2015/152108,2015,A1 .Location in patent: Paragraph 1356; 1357; 1358
[2]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 495

19
C₇H₃F₃N₄O [ No CAS ]
[ 69816-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 135℃; for 8h;	[0156] To an ice bath cooled solution of 5,6-diaminopyrimidin-4-ol (1.94g, 15.4mmol) in 3M NaOH (19. 3mL, 5 8mmol) was added 3,3 -dibromo- 1,1,1 -trifluoropropan-2-one (1.3 6m1, lOmmol). The reaction was stirred for 72h at room temperature. The reaction was acidified to PH=5 and extracted with DCM for three times. The combined organic phase was dried over sodium sulfate, filtered and concentrated. The residue was dissolved in 60% sulfuric acid (15mL) and stirred at 135C for 8hs. The reaction was cooled, poured over ice and neutralized to PH=8 with conc. ammonia and extracted with EA for 5 times. The combined organic phase was dried over sodium sulfate, filtered and concentrated. The residue was recrystallized form hexane to afford the 5-(trifluoromethyl)pyrazin-2-amine as a white solid (370mg, 22%). ?H NMR (300 MHz, CDC13) 68.31 (s, 1H), 8.01 (s, 1H), 5.43 (brs, 2H). MS (ESI) exact mass calculated for [M+H] (C5H5F3N3) requires m/z 164.04, found m/z 163.85.

Reference： [1]Patent: WO2016/81599,2016,A1 .Location in patent: Paragraph 0156

20
[ 29568-33-0 ]
[ 69816-38-2 ]
C₁₃H₉ClF₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[0157] 5-chloro-2-methoxybenzoic acid (229.0 mg, 1.226 mmol) was dissolved in TIIF (5.0 mL), followed by the addition of catalytic amount of DMF (10 .iL) and oxalyl chloride (0.127 mL, 1.472 mmol) respectively. The reaction was allowed to stir at rt for 30 mm, concentrated in vacuo, and the residue was re-dissolved in TIIF (3.0 mL). In another flask, 5- (trifluoromethyl)pyrazin-2-amine (160.0 mg, 0.981 mmol) was dissolved in TIIF (5.0 mL) followed by addition of NaH (60.0 mg, 1.47 mmol, 60% in mineral oil). The mixture was stirred for 10 minutes before it was added to the flask containing the freshly prepared acid chloride dropwise at rt. The reaction was stirred at rt for 30 mm before silica gel was added to quench the reaction. Solvent was evaporated and the resulting residue was purified via silica gel column chromatography to yield 35 as a white solid (76.0 mg, 23% yield). ?H NMR (300 MHz, cdcl3) 6 10.56 (s, 1H), 9.80 (s, 1H), 8.63 (s, 1H), 8.24 (d, J = 2.8 Hz, 1H), 7.51 (dd, J = 8.8, 2.8 Hz, 1H),7.02 (d, J = 8.9 Hz, 1H), 4.11 (s, 3H). MS (ESI) exact mass calculated for [M+Na]? (C,3H,0C1F3N302) requires m/z 332.04, found m/z 331.75. This compound (95mg, 0.287mmo1) was mixed with pyridinium chloride (1.0 g). The mixture was heated to 210 C, stirred for 15 minutes and cooled down to rt. The resulting solid was dissolved in water and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified via silica gel column chromatography to yield the title compound as a yellow solid (67.0 mg, 75% yield). ?H NMR (400 MHz, cdcl3) 6 11.23 (s, 1H), 9.71 (s, 1H), 8.78 (s, 1H), 8.69 (s, 1H), 7.61 (d, J= 2.4 Hz, 1H), 7.48 (dd, J = 8.9, 2.4 Hz, 1H), 7.04 (d, J = 9.0 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C,2H8C1F3N302) requires m/z 318.03, found m/z 317.85.

Reference： [1]Patent: WO2016/81599,2016,A1 .Location in patent: Paragraph 0157

21
[ 29568-33-0 ]
[ 69816-38-2 ]
5-chloro-2-hydroxy-N-(5-(trifluoromethyl)pyrazin-2-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/81599,2016,A1

22
[ 799557-87-2 ]
[ 69816-38-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With ammonium hydroxide; In tetrahydrofuran; at 100℃; for 1h;Microwave irradiation;	A mixture of 5-chloro-2-trifluoromethylpyrazine (2 g, 10.95 mmol) and ammoniumhydroxide (12 mL) in THF (4 mL) was heated at 100 C in a microwave reactor for 1 h. After this period, the reaction mixture was extracted with ethyl acetate and H20. The aqueous layer was extracted 3 times. The combined extracts were dried over with Mg504, filtered, and evaporated under reduce pressure to afford the amine compound 1 as a light yellow solid (1.78 g, 99%).
90%	With ammonium hydroxide; at 80℃; for 3.5h;Sealed tube;	2-Chloro-5-(trifluoromethyl)pyrazine (5.0 g, 27 mmol) (Oakwood Products, 075803) was stirred in ammonium hydroxide (190 mL, 2.7 mol) and heated to 80 C. for 3.5 h in a sealed pressure vessel. After cooling to rt, the aqueous mixture was extracted with DCM (4*). The extracts were combined, dried over sodium sulfate, filtered, and concentrated to afford the title compound as a white solid (4.0 g, 90%). 1H NMR (400 MHz, CDCl3) delta 8.34 (s, 1H), 8.01 (s, 1H), 5.01 (br s, 2H). LCMS for C5H5F3N3 (M+H)+: calculated m/z=164.0; found 164.1.
90%	With ammonium hydroxide; at 80℃; for 3.5h;Sealed tube;	2-Chloro-5-(trifluoromethyl)pyrazine (5.0 g, 27 mmol) (Oakwood Products, 075803) was stirred in concentrated ammonium hydroxide (190 mL, 2.7 mol) and heated to 80 C for 3.5 h in a sealed pressure vessel. After cooling to room temperature (rt), the aqueous mixture was extracted with DCM (4 x). The extracts were combined, dried over sodium sulfate, filtered, and concentrated to afford the title compound as a white solid (4.0 g, 90%). NMR (400 MHz, CDCI3) delta 8.34 (s, IH), 8.01 (s, IH), 5.01 (br s, 2H). LCMS for C5H5F3N3 (M+H)+: calculated m/z = 164.0; found 164.1.

Reference： [1]Patent: WO2018/211323,2018,A1 .Location in patent: Page/Page column 00223
[2]Patent: US2018/9816,2018,A1 .Location in patent: Paragraph 1377; 1378
[3]Patent: WO2019/79469,2019,A1 .Location in patent: Page/Page column 157-158

23
[ 69816-38-2 ]
3-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-8-amine [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1
[2]Patent: WO2019/79469,2019,A1

24
[ 69816-38-2 ]
tert-butyl (R)-(1-((3-(8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl)-4-methylphenyl)sulfonyl)piperidin-3-yl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

25
[ 69816-38-2 ]
3-(8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl)-4-methylbenzene-1-sulfonyl chloride [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

26
[ 69816-38-2 ]
(R)-3-(5-((3-aminopiperidin-1-yl)sulfonyl)-2-methylphenyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-8-amine tris(2,2,2-trifluoroacetate) [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

27
[ 69816-38-2 ]
2-amino-3-chloro-5-(trifluoromethyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-chloro-succinimide; In 1-methyl-pyrrolidin-2-one; at 20℃; for 6h;	5-(Trifluoromethyl)pyrazin-2-amine (4.56 g, 28.0 mmol) was stirred in NMP (135 mL, 1400 mmol) and N-chlorosuccinimide (3.73 g, 28.0 mmol) was added. The reaction mixture was stirred at rt for 6 h. The reaction mixture was poured into sat. sodium thiosulfate (100 mL) and diluted with water (500 mL). The mixture was extracted with ethyl acetate (4200 mL). The combined extracts were washed with brine (3), dried over sodium sulfate, filtered, and concentrated. Purification via silica gel column (0-35% EtOAc/hexanes) afforded the title compound as a white solid (2.32 g, 42.0%). LCMS for C5H4ClF3N3 (M+H)+: calculated m/z=198.0; found 198.0.
42%	With N-chloro-succinimide; In 1-methyl-pyrrolidin-2-one; at 20 - 30℃; for 6h;	5-(Trifluoromethyl)pyrazin-2-amine (4.56 g, 28.0 mmol) was stirred in /V-methyl-2- pyrrolidone (NMP, 135 mL, 1400 mmol) and N-chlorosuccinimide (3.73 g, 28.0 mmol) was added. The reaction mixture was stirred at rt for 6 h. The reaction mixture was poured into sat. sodium thiosulfate (100 mL) and diluted with water (500 mL). The mixture was extracted with ethyl acetate (4 x 200 mL). The combined extracts were washed with brine (3x), dried over sodium sulfate, filtered, and concentrated. Purification via silica gel column (0-35% EtOAc/hexanes) afforded the title compound as a white solid (2.32 g, 42.0%). LCMS for C5H4C1F3N3 (M+H)+: calculated m/z = 198.0; found 198.0.

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 1525 - 1529
[2]Patent: US2018/9816,2018,A1 .Location in patent: Paragraph 1379; 1380
[3]Patent: WO2019/79469,2019,A1 .Location in patent: Page/Page column 158

28
[ 69816-38-2 ]
8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyrazine [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1
[2]Patent: WO2019/79469,2019,A1

29
[ 69816-38-2 ]
3-bromo-8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyrazine [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1
[2]Patent: WO2019/79469,2019,A1

30
[ 69816-38-2 ]
3-bromo-N-(4-methoxybenzyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-8-amine [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1
[2]Patent: WO2019/79469,2019,A1

31
[ 69816-38-2 ]
3-(o-tolyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-8-amine [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

32
[ 69816-38-2 ]
(1-((3-(8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl)-4-methylphenyl)sulfonyl)piperidin-3-yl)methanol [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

33
[ 69816-38-2 ]
8-chloro-3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyrazine [ No CAS ]

Reference： [1]Patent: US2018/9816,2018,A1

34
2-bromo-1-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethan-1-one [ No CAS ]
[ 69816-38-2 ]
2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38 mg	for 5h;Reflux;	103 mg of <strong>[69816-38-2]5-(trifluoromethyl)pyrazin-2-amine</strong> was dissolved in 4 ml of bromobenzene, and 30 mg of 2-bromo-1-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone was added at room temperature. After the addition, the reaction mixture was stirred under reflux with heating for 5 hours. After the reaction, the reaction mixture was mixed with 10 ml of a 1M sodium hydroxide aqueous solution and extracted with ethyl acetate (10 ml*2). The resulting organic layer was dehydrated with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 10:0 to 0:10) as the eluent to obtain 38 mg of the desired product as a white solid. Melting point: 266-270 C. 1H-NMR (CDCl3): delta9.63 (s, 1H), 9.24 (s, 1H), 8.68 (s, 1H), 8.62 (s, 1H), 7.93 (d, J=9.3 Hz, 1H), 7.66 (dd, J=9.3, 1.8 Hz, 1H), 3.70 (q, J=7.5 Hz, 2H), 1.35 (t, J=7.5 Hz, 3H).

Reference： [1]Patent: US2018/22760,2018,A1 .Location in patent: Paragraph 1073; 1074; 1075

35
[ 69816-38-2 ]
[ 1173881-90-7 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 354 - 358

36
[ 69816-38-2 ]
N<SUP>2</SUP>-(pentan-3-yl)-6-(trifluoromethyl)pyrazine-2,3-diamine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 354 - 358

37
[ 69816-38-2 ]
1-(pentan-3-yl)-6-(trifluoromethyl)-1H-imidazo[4,5-b]pyrazin-2-ol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 354 - 358

38
2-bromo-1-(3,6-difluoropyridin-2-yl)ethanone [ No CAS ]
[ 69816-38-2 ]
2-(3,6-difluoropyridin-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 120h;	5-(Trifluoromethyl)pyrazin-2-amine (500 mg, 3.06 mmol, 1 eq.) and 2-bromo-1-(3,6-difluoropyridin-2-yl)ethanone (1.02 g, 3.67 mmol, 2 eq.) were dissolved in 15 ml of ethanol and heated at 60 C. for 5 d. The reaction mixture was concentrated and recrystallized from dichloromethane/methyl tert-butyl ether. log P (acidic): 2.05; MH+: 301; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 9.39 (s, 1H), 9.31 (s, 1H), 8.80-8.79 (m, 1H), 8.18-8.11 (m, 1H), 7.37-7.33 (m, 1H).

Reference： [1]Patent: US2018/271099,2018,A1 .Location in patent: Paragraph 1060-1062

39
[ 69816-38-2 ]
(S)-3-(2,5-dichloro-4-(5-(6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)propane-1,2-diol [ No CAS ]

Reference： [1]Patent: WO2018/211323,2018,A1

40
[ 69816-38-2 ]
(R)-3-(2,5-dichloro-4-(5-(6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)propane-1,2-diol [ No CAS ]

Reference： [1]Patent: WO2018/211323,2018,A1

41
[ 69816-38-2 ]
[ 1372197-49-3 ]

Reference： [1]Patent: WO2018/211323,2018,A1

42
[ 69816-38-2 ]
C₁₆H₈Cl₂F₃N₅O₂ [ No CAS ]

Reference： [1]Patent: WO2018/211323,2018,A1

43
[ 69816-38-2 ]
C₁₅H₆Cl₂F₃N₅O₂ [ No CAS ]

Reference： [1]Patent: WO2018/211323,2018,A1

44
[ 69816-38-2 ]
C₂₀H₁₄Cl₂F₃N₅O₄ [ No CAS ]

Reference： [1]Patent: WO2018/211323,2018,A1

45
[ 69816-38-2 ]
2-(2,5-dichloro-4-(5-(6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)propan-1-ol [ No CAS ]

Reference： [1]Patent: WO2018/211323,2018,A1

46
[ 69816-38-2 ]
1-(3-(8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl)-4-methylphenyl)-2,2,2-trifluoro-1-(1-methyl-1H-tetrazol-5-yl)ethan-1-ol trifluoroacetic acid salt [ No CAS ]