486460-21-3|3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine| Ambeed

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Quality Control of [ 486460-21-3 ] Purity: 98% SDS Specification

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Product Details of [ 486460-21-3 ]

CAS No. :	486460-21-3
Formula :	C₆H₇F₃N₄
M.W :	192.14
SMILES Code :	FC(C1=NN=C2CNCCN21)(F)F
MDL No. :	MFCD08460920
InChI Key :	FMTDZGCPYKWMPT-UHFFFAOYSA-N
Pubchem ID :	10176489

Safety of [ 486460-21-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 486460-21-3 ]

* 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.

Downstream synthetic route of [ 486460-21-3 ]

[ 486460-21-3 ] Synthesis Path-Downstream 1~35

1
[ 913623-68-4 ]
[ 486460-21-3 ]
C₂₄H₂₅N₅O₃F₆ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6439 - 6442.

2
[ 874359-92-9 ]
[ 486460-21-3 ]
[ 874360-10-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3384 - 3387.

3
[ 874360-01-7 ]
[ 486460-21-3 ]
C₂₆H₂₅F₆N₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3384 - 3387.

4
C₂₁H₁₇ClF₇NO₂ [ No CAS ]
[ 486460-21-3 ]
C₂₇H₂₃F₁₀N₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5191 - 5198.

5
[ 486460-21-3 ]
((4R,5S)-5-amino-4-(2,4,5-trifluorophenyl)cyclohex-1-enyl)(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6439 - 6442.

6
[ 486460-21-3 ]
7-[(3R)-3-amino-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 49 - 52.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 141 - 151.

7
[ 486460-21-3 ]
[ 486460-32-6 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 141 - 151.
[2]Patent: CN106146514,2016,A .
[3]Patent: CN104447753,2017,B .
[4]Patent: CN104447753,2017,B .
[5]Patent: CN108178761,2018,A .
[6]Patent: CN108314688,2018,A .

8
[ 486460-21-3 ]
7-[(3R)-3-amino-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 141 - 151.

9
[ 486460-21-3 ]
3-amino-4-(3,4-difluoro-phenyl)-1-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-butan-1-one; hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 141 - 151.

10
[ 486460-21-3 ]
Sitagliptin hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 141 - 151.

11
trifluoro-acetic acid N'-pyrazin-2-yl-hydrazide; compound with trifluoro-acetic acid [ No CAS ]
[ 486460-21-3 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 141 - 151.

12
C₁₂H₂₀N₂O₆ [ No CAS ]
[ 486460-21-3 ]
[3-oxo-1-(2-oxo-oxazolidin-3-ylmethyl)3-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)propyl]-(1S)-carbamic acid t-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3S-t-butoxycarbonylamino-4-(2-oxo-oxazolidin-3-yl)-butyric acid benzyl ester obtained in PREPARATION 16 was dissolved in methanol, then 3 mg of palladium/ carcol (Pd/C) was added thereto, followed by stirring under hydrogen atmosphere for 3 hours, 40 minutes. After completion of a reaction, the reaction solution was filtered by Cellite, and then washed with methanol, concentrated. To this reaction, 15 mg (0.079 mmol) of 3-trifluoromethyl-5,6-dihydro-8H-[l,2,4]triazolo[4,3-a]pyrazine was added immediately, then was dissolved in dichloromethane. The reaction was cooled to 0C, then 13 mg (0.095 mmol) of HOBT was added, then stirred for 10 minutes, 23 mg (0.12 mmol) of EDC was added to thereto. After removal of an icebath, the reaction solution was stirred for abour 17 hours, then the concentrated residue was purified by prep-TLC (10:1 CH Cl :MeOH) to give 21 mg of the title compound in a total yield of 57%.[539] 1K NMR (CDCl3) delta 5.6-5.8(1H, m), 4.9-5.1(2H, m), 4.0-4.4(6H, m), 3.6-3.8(2H, m), 3.3-3.5(2H, m), 2.6-2.9(2H, m), 1.39 (9H, s)[540] Mass (m/e) 463 (M+l)

References: [1]Patent: WO2006/104356,2006,A1 .Location in patent: Page/Page column 38.

13
C₁₃H₂₂N₂O₆ [ No CAS ]
[ 486460-21-3 ]
[1-(5-methyl-2-oxo-oxazolidin-3-ylmethyl)-3-oxo-3-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)propyl]-(1S)-carbamic acid t-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3S-t-butoxycarbonylamino-4-(5-methyl-2-oxo-oxazolidin-3-yl)-butyric acid benzyl ester 120 mg (0.31 mmol) of obtained in PREPARATION 19 was dissolved in methanol, then 12 mg of palladium/carcol (Pd/C) was added thereto, followed by stirring under hydrogen atmosphere for 3 hours, 40 minutes. After completion of a reaction, the reaction solution was filtered by Cellite, then washed with methanol, followed by concentration. 9 mg (0.31 mmol) of amine was added immediately thereto, then the resulting solution was dissolved in dichloromethane. The reaction was cooled to 0C, then 50 mg (0.37 mmol) of HOBT was added there. After stirring for 10 minutes, 88 mg (0.47 mmol) of EDC was added to thereto. After removal of an icebath, the reaction solution was stirred for abour 17 hours, then the concentrated residue was purified by prep-TLC (10:1 CH Cl :MeOH) to give 88 mg of the title compound in a total yield of 60%.[560] 1K NMR (CDCl3) delta 5.6-5.9(1H, m), 4.9-5.1(2H, m), 4.6-4.8 (IH, m), 3.9-4.3 (5H, m), 3.6-3.8 (IH, m), 3.1-3.5 (3H, m), 2.5-2.9 (2H, m), 1.40(12H, m)[561] Mass (m/e) 477 (M+l)

References: [1]Patent: WO2006/104356,2006,A1 .Location in patent: Page/Page column 40.

14
[ 1024501-15-2 ]
[ 486460-21-3 ]
[ 911634-86-1 ]

Yield	Reaction Conditions	Operation in experiment
53%		333 mg (1 mmol) of 3S-t-butoxycarbonylamino-4-(t-butyl-dimethyl-silanyloxy)- butanoic acid which was obtained from step (1) was added 192 mg (1 mmol) of 3-trifluoromethyl-5,6-dihydro-8H-[l,2,4]triazolo[4,3-a]pyrazine, and the resulting mixture was dissolved in dichloromethane. The reaction solution was cooled to 0C, and 162 mg (1.2 mmol) of HOBT was added, followed by stirring for 10 minutes and then addition of 288 mg (1.5 mmol) of EDC. After removal of an icebath, the reaction solution was stirred for abour 13 hours, and then the residue, which was obtained by concentration was purified by column chromatography (1:1 hexane: ethyl acetate) to give 0.27 g of the title compound in yield of 53%.[582] 1H NMR (CDCl3) delta 5.1-5.3 (IH, m), 4.9-5.1(2H, m), 3.9-4.3 (4H, m), 3.7-3.8 (2H, m), 2.6-2.9 (2H, m), 1.40(9H, s), 0.87 (9H, s), 0.03 (6H, s)[583] Mass (m/e) 508 (M+l)

References: [1]Patent: WO2006/104356,2006,A1 .Location in patent: Page/Page column 42.

15
[trans-5-nitro-4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]methyl methanesulfonate [ No CAS ]
[ 486460-21-3 ]
C₁₉H₁₇F₆N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; for 48h;	Example 19E (66 mg, 0.18 mmol), <strong>[486460-21-3]3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine</strong> (prepared as described in D. Kim et al, J. Med. Chem. 2005, 48, 141-151). 41.6 mg, 0.216 mmol), and triethyl amine (62.6 mL, 0.45 mumol) were mixed in 1 mL of methylene chloride and stirred for two days. The mixture was then purified by flash chromatography (eluting with 60-70% ethyl acetate/hexane) to give the desired nitro amine.

References: [1]Patent: US2007/49596,2007,A1 .Location in patent: Page/Page column 33.

16
[ 24424-99-5 ]
[ 486460-21-3 ]
[ 877402-43-2 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 589 - 602.

17
[ 25115-74-6 ]
[ 486460-21-3 ]
[ 1037235-17-8 ]
1,4-cis-1-phenyl-4-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-cyclohexanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1 A-trans-lambda -Phenyl-4-(3-trifluoromethyl-5.6-dihydro-8H-f 1.2.41triazolof4.3-alpyrazin-7-yl)- cyclohexanecarbonitrileTo a solution of 4-oxo-1-phenyl-cyclohexanecarbonitrile (100mg, 0.50 mmol) in 1,2- dichloroethane (1ml) were successively added S-trifluoromethyl-S.betaJ.delta-tetrahydro- [1,2,4]triazolo[4,3-a]pyrazine (106mg, 0.55 mmol), sodium triacetoxyborohydride (168mg, 0.75 mmol), and acetic acid (29 mul, 0.50 mmol). The reaction was stirred at RT for 2hrs before diluted with EtOAc and quenched with water. The resulting mixture was extracted twice with EtOAc, and the combined organic phase was washed once with brine, dried over Na2SO4, and evaporated to provide pale yellow solid. Purification by preparative HPLC yielded the title compound (100mg) along with its stereoisomer 1,4-c/s-1-Phenyl-4-(3- <n="160"/>trifluoromethyl-S.e-dihydro-deltaH-II ^^Jtriazolomu.a-alpyrazin-y-yO-cyclohexanecarbonitrile (18mg), both as white solids. MS: 376.0 [M +H]+

References: [1]Patent: WO2008/77597,2008,A1 .Location in patent: Page/Page column 101; 158; 159.

18
[ 1037235-26-9 ]
[ 486460-21-3 ]
[ 1037235-28-1 ]
[ 1037235-30-5 ]

Yield	Reaction Conditions	Operation in experiment
		((c/s-1-(3-Chlorophenyl)-4-f3-(trifluoromethyl)-5.6-dihvdrori.2.4ltriazolof4.3-a1pyrazin- 7(8H)-yl1cvclohexyl)methyl)-carbamic acid tert-butyl ester and ((^ra/7s-1-(3-chlorophenyl)-4- f3-(triflupsilonoromethyl)-5.6-dihvdrof1.2.41triazolof4.3-a1pyrazin-7(8H)-vncvclohexyl>methyl)- carbamic acid tert-butyl esterSodium triacetoxyborohydride (316mg, 1.49mmol) was added to a solution of [1-(3- chlorophenyl)-4-oxo-cyclohexylmethyl]-carbamic acid tert-butyl ester (360mg, 1.07mmol) and 3-trifluoromethyl-5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine (286.4mg, 1.49mmol) in 1 ,2-dichloroethane and the mixture was stirred at room temperature for 24h. The reaction was quenched with water and the product was extracted with ethyl acetate. The organic extracts were washed with brine, dried and concentrated in vacuo to give a yellow oil. The oil <n="164"/>was purified by flash chromatography (silica, eluting with 1 :33:66 2M ammonia in methanol:ethyl acetatexyclohexane) to afford the individual title compounds as white solids.Cis diastereoisomer:MS (ES+): 514[M+H]+.TR [HPLC, Phenomenex Luna 3 micron C18; 5-95% CH3CN+0.1%Formic acid/H2O+0.1%Formic acid for 5 min, flow 2.0 ml/min]: 3.70 min.Trans diastereoisomer:MS (ES+): 514[M+H]TR [HPLC, Phenomenex Luna 3 micron C18; 5-95% CH3CN+0.1%Formic acid/H2O+0.1%Formic acid for 5 min, flow 2.0 ml/min]: 3.57min

References: [1]Patent: WO2008/77597,2008,A1 .Location in patent: Page/Page column 102; 162; 163.

19
C₁₄H₂₄N₂O₅ [ No CAS ]
[ 486460-21-3 ]
[3-oxo-1-(2-oxo-piperidin-1-ylmethyl)-3-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-propyl]-(1S)-carbamic acid t-butyl ester [ No CAS ]
C₂₀H₂₉F₃N₆O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3706 - 3710.

20
[ 1150656-17-9 ]
[ 486460-21-3 ]
C₂₁H₃₂F₃N₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1908 - 1912.

21
[ 1150656-18-0 ]
[ 486460-21-3 ]
C₂₂H₃₄F₃N₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1908 - 1912.

22
[ 1150656-19-1 ]
[ 486460-21-3 ]
C₂₂H₃₄F₃N₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1908 - 1912.

23
[ 30924-93-7 ]
[ 486460-21-3 ]
C₂₃H₂₈F₃N₅O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1908 - 1912.

24
[ 87219-29-2 ]
[ 486460-21-3 ]
[ 1242069-61-9 ]

Yield	Reaction Conditions	Operation in experiment
73%		Example 1 : Preparation of (S)-benzyl 1-hydroxy-4-oxo-4-(3-(trifluoromethyl)- 5,6-dihydro-ri ,2,41triazolor4,3-aipyrazin-7(8H)-yl)butan-2-ylcarbamate A 2.0 M solution of AIMe3 in hexanes (0.98 ml_, 1.96 mmol) was added to a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine (271 mg, 1.41 mmol) in anhydrous methylene chloride (5 ml_). The resulting mixture was added dropwise to a solution of (S)-benzyl 5-oxotetrahydrofuran- 3-ylcarbamate (265 mg, 1.13 mmol) in anhydrous methylene chloride (5 ml_) at 0 0C. When the reaction was completed, 1 M KHSO4 solution (25 ml_) was added slowly. The layers were separated and the aqueous layer was extracted with methylene chloride (25 ml_). The organic layers were mixed, dried over anhydrous Na2SO4, filtered and concentrated to dryness to yield (S)-benzyl 1 -hydroxy-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro- [1 ,2,4]triazolo[4,3-a] pyrazin-7(8H)-yl)butan-2-ylcarbamate (353 mg, 0.83 mmol, 73% yield).

References: [1]Patent: WO2010/97420,2010,A1 .Location in patent: Page/Page column 18.

25
[ 1244732-97-5 ]
[ 486460-21-3 ]
[ 1243255-09-5 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 6572 - 6583.

26
[ 79-04-9 ]
[ 486460-21-3 ]
[ 1119004-07-7 ]

Yield	Reaction Conditions	Operation in experiment
89%		The resulting product is dissolved in tetrahydrofuran (200 ml) and the solution is added in about 90 minutes to a solution obtained dissolving chloroacetyl chloride (28.6 g, 253 mmol) in tetrahydrofuran (200 ml), under N2 atmosphere and under stirring. The solution is left under stirring at 25C for 1 h. After completion of the reaction, a 25% NaOH solution (80 g) is added, the phases are separated and the aqueous phase is extracted with 2x100 ml of tetrahydrofuran. The solvent is concentrated under reduced pressure to obtain 160 g of a crude, which is added with methyl-tert-butyl ether (220 ml) and the solution is heated under reflux of the solvent mixture. The solution is cooled to 10C under strong stirring for 3h. The product (56.1 g, 209 mmol, 89% yield) is a white solid.

References: [1]Patent: EP2270009,2011,A1 .Location in patent: Page/Page column 10.

27
[ 762240-92-6 ]
[ 486460-21-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; In water; ethyl acetate; for 0.166667h;Product distribution / selectivity;	Example 4 Synthesis 7-chloroacetyl-3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine of formula (VIII, Q = chlorine) 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (54.6 g, 239 mmol) is suspended in ethyl acetate (300 ml) and added, under strong stirring, with a 30% NaOH solution (100 g) and water (50 ml). After 10 minutes the phases are separated, the aqueous phase is extracted with 3x70 ml of ethyl acetate and the organic phase is dried with Na2SO4, then filtered and the solvent is evaporated off under reduced pressure to obtain a white solid (45.4 g, 236 mmol, 99% yield).

References: [1]Patent: EP2270009,2011,A1 .Location in patent: Page/Page column 9-10.

28
[ 863679-83-8 ]
[ 486460-21-3 ]
[ 1259556-59-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 6h;Reflux;	To a solution of l-(4-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (Intermediate I, 400 mg, 1.18 mmol) in anhydrous toluene (5 mL) were added Pd2(dba)3 (5.4 mg, 0.006 mmol), BINAP (11.0 mg, 0.018 mmol), sodium tert-butoxide (227 mg, 2.34 mmol) and 3-trifluoromethyl-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine (prepared by the procedure as described in reference J. Med. Chem., 2005, 48, 141-151) (340 mg, 1.77 mmol) at r.t. and reaction mixture was refluxed for 6h. Reaction mixture was then concentrated and the crude product was purified by column chromatography (silica gel, 6: 4 EtOAc: Pet. ether) to afford the title compound as white solid (330 mg, 62%). ESIMS (m/z): 472.9 (M+23), 451.9 (M+2), 450.8 (M+l).
62%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 20℃; for 6h;Reflux;	Step 1: Preparation of 1-[4-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-phenyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl esterTo a solution of 1-(4-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (Intermediate I, 400 mg, 1.18 mmol) in anhydrous toluene (5 mL) were added Pd2(dba)3 (5.4 mg, 0.006 mmol), BINAP (11.0 mg, 0.018 mmol), sodium tert-butoxide (227 mg, 2.34 mmol) and <strong>[486460-21-3]3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine</strong> (prepared by the procedure as described in reference J. Med. Chem., 2005, 48, 141-151) (340 mg, 1.77 mmol) at r.t. and reaction mixture was refluxed for 6 h. Reaction mixture was then concentrated and the crude product was purified by column chromatography (silica gel, 6:4 EtOAc:Pet. ether) to afford the title compound as white solid (330 mg, 62%).ESIMS (m/z): 472.9 (M+23), 451.9 (M+2), 450.8 (M+1).

References: [1]Patent: WO2010/150281,2010,A2 .Location in patent: Page/Page column 95.
[2]Patent: US2012/165320,2012,A1 .Location in patent: Page/Page column 55.

29
[ 1292321-39-1 ]
[ 486460-21-3 ]
C₂₅H₃₂F₅N₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1880 - 1886.

30
[ 1286756-59-9 ]
[ 486460-21-3 ]
[ 1286756-60-2 ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 2824 - 2827.
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 3605 - 3607.
[3]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1961 - 1970.

31
[ 1150656-76-0 ]
C₁₃H₁₈N₂O₂ [ No CAS ]
[ 486460-21-3 ]