[ CAS No. 233278-56-3 ] {[proInfo.proName]}

Name: 233278-56-3|5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine|97%
Brand: Ambeed
SKU: A118468
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Quality Control of [ 233278-56-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 233278-56-3 ]

Product Details of [ 233278-56-3 ]

CAS No. :	233278-56-3	MDL No. :	MFCD09835083
Formula :	C₅H₈N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DXJKRLHHCGXHMB-UHFFFAOYSA-N
M.W :	124.14	Pubchem ID :	18406919
Synonyms :

Calculated chemistry of [ 233278-56-3 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.6
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.66
TPSA :	42.74 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) :	-7.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.07
Log Po/w (XLOGP3) :	-0.88
Log Po/w (WLOGP) :	-1.15
Log Po/w (MLOGP) :	-0.98
Log Po/w (SILICOS-IT) :	0.14
Consensus Log Po/w :	-0.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.47
Solubility :	42.4 mg/ml ; 0.342 mol/l
Class :	Very soluble
Log S (Ali) :	0.46
Solubility :	362.0 mg/ml ; 2.91 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.88
Solubility :	16.6 mg/ml ; 0.133 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.19

Safety of [ 233278-56-3 ]

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 [ 233278-56-3 ]

* 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.

Upstream synthesis route of [ 233278-56-3 ]
Downstream synthetic route of [ 233278-56-3 ]

[ 233278-56-3 ] Synthesis Path-Upstream 1~2

1
[ 399-66-6 ]
[ 233278-56-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen In 2-methoxy-ethanol for 21.5 h;	Platinum(IV) oxide (2.75 g, 12.1 mmol) was added, under nitrogen, to a suspension of calcium oxide (9.30 g, 166 mmol) and [1,2,4]triazolo[1,5-a]pyrazine (18.10 g, 151 mmol) in 2-methoxyethanol (150 ml). The reaction mixture was stirred for 21.5 h under a hydrogen atmosphere, filtered over Celite, and washed with dichloromethane/ethanol (9:1). The filtrate was concentrated, coevaporated with toluene and diisopropyl ether, and then dissolved in ethyl acetate, filtered over Celite, washed with ethyl acetate and concentrated again. The residue was dissolved in hot diisopropyl ether, filtered, washed with diisopropyl ether, and concentrated for 7 h in vacuo. Yield: 17.12 g (92percent)

Reference： [1] Patent: US2008/153843, 2008, A1, . Location in patent: Page/Page column 68
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[3] Patent: WO2006/9886, 2006, A1, . Location in patent: Page/Page column 46
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 5934 - 5939
[5] Patent: WO2009/90055, 2009, A1, . Location in patent: Page/Page column 108; 109

2
[ 1575612-94-0 ]
[ 233278-56-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706

[ 233278-56-3 ] Synthesis Path-Downstream 1~17

1
[ 399-66-6 ]
[ 233278-56-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen;platinum(IV) oxide; In 2-methoxy-ethanol; for 21.5h;	Platinum(IV) oxide (2.75 g, 12.1 mmol) was added, under nitrogen, to a suspension of calcium oxide (9.30 g, 166 mmol) and <strong>[399-66-6][1,2,4]triazolo[1,5-a]pyrazine</strong> (18.10 g, 151 mmol) in 2-methoxyethanol (150 ml). The reaction mixture was stirred for 21.5 h under a hydrogen atmosphere, filtered over Celite, and washed with dichloromethane/ethanol (9:1). The filtrate was concentrated, coevaporated with toluene and diisopropyl ether, and then dissolved in ethyl acetate, filtered over Celite, washed with ethyl acetate and concentrated again. The residue was dissolved in hot diisopropyl ether, filtered, washed with diisopropyl ether, and concentrated for 7 h in vacuo. Yield: 17.12 g (92%)
	With hydrogen;palladium 10% on activated carbon; In ethanol;	Step D: 5,6,7,8-Tetrahydrof 1,2,41triazolof 1,5-alpyrazine; A mixture of [l,2,4]triazolo[l,5-a]pyrazine (10 g) in ethanol (150 mL) and 10% Pd-C (3 g) was stirred under a hydrogen atmosphere overnight and filtered over Celite. The filtrate was evaporated and the residue purified by column chromatography (silica, 10% methanol/dichlorornethane) to yield 5,6,7,8-tetrahydro[l,2,4]triazolo[l,5-a]pyrazine. LC-MS 125.1 (M+ 1).
	With hydrogen; calcium oxide;platinum(IV) oxide; In 2-methoxy-ethanol; for 21.5h;	Stage 4. Platinum (IV) oxide (2.75 g, 12.1 mmole) was added to a suspension, saturated with nitrogen, of CaO (9.30 g, 166 mmole) and [ 1, 2 , 4 ] -triazolo [ 1, 5-a] pyrazine (18.1 g, 151 mmole) in methoxyethanol (150 ml) . The reaction mixture was stirred for 21.5 hours under a hydrogen atmosphere. The catalyst was filtered off through filter earth and washed with DCM/ethanol (9:1). The filtrate was concentrated, and the solvent was removed firstly with <n="110"/>toluene and then with 2-propanol. The residue was taken up in ethyl acetate, filtered again through filter earth, washed with ethyl acetate, and concentrated. The residue was washed with hot 2-propanol and concentrated in vacuo.

Reference： [1]Patent: US2008/153843,2008,A1 .Location in patent: Page/Page column 68
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 3687 - 3706
[3]Patent: WO2006/9886,2006,A1 .Location in patent: Page/Page column 46
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5934 - 5939
[5]Patent: WO2009/90055,2009,A1 .Location in patent: Page/Page column 108; 109

2
[ 344778-59-2 ]
[ 233278-56-3 ]
[ 344778-62-7 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 4 5-[5,6-Dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl]-3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazoline Prepared from <strong>[233278-56-3]5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine</strong> as described for Example 1, step c (0.047 g, 53%). Found: C, 62.52; H, 3.96; N, 29.10. C20H15FN8 requires C, 62.17; H, 3.91; N, 29.00%. deltaH (360 MHz; CDCl3) 4.16 (2H, dd, J=5 and 5), 4.61 (2H, dd, J=5 and 5), 5.02 (2H, s), 7.22-7.33 (2H, m), 7.40-7.42 (1H, m), 7.71 (1H, dd, J=8 and 8), 7.95-8.08 (4H, m), 8.75 (1H, d, J=8); m/z (ES+) 387 (M+H+).

Reference： [1]Patent: US2003/45532,2003,A1

3
[ 233278-56-3 ]
[ 486460-00-8 ]
C₂₀H₂₄F₃N₅O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5934 - 5939

4
[ 233278-56-3 ]
[ 224633-15-2 ]
[ 914654-57-2 ]

Yield	Reaction Conditions	Operation in experiment
28%	With triethylamine; In N,N-dimethyl-formamide; at 60℃; for 40h;	Description 35: 3-(5,6-Dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-ylmethyl)-2-phenylquinoline-4-carboxylic Acid A mixture of 3-(bromomethyl)-2-phenylquinoline-4-carboxylic acid (Description 5, 3.4 g, 10.3 mmol), <strong>[233278-56-3]5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine</strong> (1.24 g, 9.1 mmol) and triethylamine (1.39 mL, 1.01 g, 10 mmol) in DMF (50 mL) was heated at 60 C. for 40 h. The mixture was cooled and the solvent was evaporated under reduced pressure. EtOAc (500 mL) was added and the mixture was heated to reflux, filtered and cooled. The solvent was evaporated under reduced pressure to a volume of 100 mL and the solid was collected and dried in vacuo to give the title compound as a solid (1.0 g, 28%). m/z (ES+) 386 [M+H+].

Reference： [1]Patent: US2009/54440,2009,A1 .Location in patent: Page/Page column 31

5
[ 873924-08-4 ]
[ 233278-56-3 ]
[ 1246508-02-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃;	Step 1: tert-Butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate Acetic acid (2.34 eq.) was added to a solution of <strong>[873924-08-4]tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate</strong> (1.122 mmol, 1 eq.) and 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (1.14 eq.) in methylene chloride (7 ml). Sodium triacetoxyborhydride (1.4 eq) was then added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride and sat. NaHCO3 solution. The aqueous phase was washed with methylene chloride (2*20 ml), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (silica, ethyl acetate/ethanol 10:1) to obtain the desired product. Yield: 62%

Reference： [1]Patent: US2010/249095,2010,A1 .Location in patent: Page/Page column 126

6
[ 763114-26-7 ]
[ 233278-56-3 ]
[ 1358715-11-3 ]

Yield	Reaction Conditions	Operation in experiment
21.0%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 20h;Inert atmosphere;	2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (360 mg, 1.20 mmol) was dissolved in 10 mL of N, N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N, N, N', N'-tetramethyluronium hexafluorophosphate (600 mg, 1.80 mmol), <strong>[233278-56-3]5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine</strong> 16a (150 mg, 1.20 mmol, prepared according to a known method disclosed by 'patent application ') and N, N-diisopropylethylamine (0.4 mL, 2.40 mmol). After stirring for 20 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazine-7-carbonyl)-4-fluorophenyl]methyl]-2H-phthalazin-1-one 16 (100 mg, yield 21.0%) as a yellow solid. MS m/z (ESI): 405.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.47 (br. s, 1H), 8.51-8.49 (m, 1H), 7.99-1.77 (m, 4H), 7.42-7.30 (m, 2H), 7.30-7.12 (m, 1H), 4.76 (m, 2H), 4.37-4.28 (m, 4H), 3.77-3.73 (m, 2H)
21.0%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 20h;	Example 16 4-[[3-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (360 mg, 1.20 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (600 mg, 1.80 mmol), <strong>[233278-56-3]5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine</strong> 16a (150 mg, 1.20 mmol, prepared according to a known method disclosed by "patent application WO2009090055") and N,N-diisopropylethylamine (0.4 mL, 2.40 mmol). After stirring for 20 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 16 (100 mg, yield 21.0%) as a yellow solid. MS m/z (ESI): 405.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.47 (br. s, 1H), 8.51-8.49 (m, 1H), 7.99-1.77 (m, 4H), 7.42-7.30 (m, 2H), 7.30-7.12 (m, 1H), 4.76 (m, 2H), 4.37-4.28 (m, 4H), 3.77-3.73 (m, 2H)

Reference： [1]Patent: EP2604610,2013,A1 .Location in patent: Paragraph 0127; 0128
[2]Patent: US2013/131068,2013,A1 .Location in patent: Paragraph 0187; 0188; 0189; 0190

7
[ 233278-56-3 ]
[ 1446819-23-3 ]
[ 1460032-62-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90℃;Inert atmosphere;	Step 1: Preparation of tert-butyl 4-[(4-chloro-2-[5H,6H,7H,8H-[l,2,4]triazolo[l,5- a]pyrazin-7-yl]phenyl)methyl]piperazine-l-carboxylate [00319] A 40-mL vial was purged with and maintained an inert atmosphere of nitrogen then was charged with tert-butyl 4-[(2-bromo-4-chlorophenyl)methyl]piperazine-l-carboxylate (600 mg, 1.54 mmol, 1.00 equiv), 5H,6H,7H,8H-[l,2,4]triazolo[l,5-a]pyrazine (229 mg, 1.84 mmol, 1.20 equiv), Cs2C03 (1.00 g, 3.10 mmol, 2.00 equiv), 2,2'-bis(diphenylphosphino)-l, l'- binaphthyl (144 mg, 0.230 mmol, 0.15 equiv), Pd2(dba)3 (70.0 mg, 0.080 mmol, 0.05 equiv), and toluene (15 mL). The resulting solution was stirred overnight at 90 C and then was diluted with water (20 mL) and extracted with dichloromethane (3 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (20/80) to provide 500 mg (75% yield) of tert-butyl 4-[(4-chloro-2- [5H,6H,7H,8H-[l,2,4]triazolo[l,5-a]pyrazin-7-yl]phenyl)methyl]piperazine-l-carboxylate as a yellow solid. LCMS (ESI, m/z): 433 [M+H]+.

Reference： [1]Patent: WO2013/142307,2013,A1 .Location in patent: Paragraph 00319

8
[ 1575612-94-0 ]
[ 233278-56-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3687 - 3706

9
[ 233278-56-3 ]
[ 124627-86-7 ]
[ 1575608-04-6 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3687 - 3706

10
[ 233278-56-3 ]
C₂₁H₂₆ClFN₄O₂Si [ No CAS ]
C₂₀H₁₉FN₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Parallel preparation of Examples 165-195: To a set of vials containing the chloropyrimidine core from Scheme H (25 mg, 0.056 mmol) in DMSO (0.3 mL) was individually added the requisite amine (0.067 mmol) and diisopropylethylamine (0.039 mL, 0.223 mmol). The vials were capped and the mixtures were heated to 1 10C with stirring for 3 hours. The mixtures were cooled to RT. Water (2 mL) was added to each vial. The aqueous phase from each vial was extracted with DCM (2 x 1 mL). The organic layers from each vial were transferred to a clean vial and the solvent was removed in vacuo. To each vial was then added THF:MeOH (1 :3, 1 mL) followed by HCI (4 N in dioxane, 0.20 mL, 0.80 mmol). The vials were capped and the solutions were heated to 70C for 0.5 h. The solutions were allowed to cool to RT and the solvent was then removed from the vials in vacuo. Each crude product was redissolved in 1 mL of DMSO and filtered. The crude products (excluding Example 195) were purified by mass triggered HPLC using the following conditions: [Waters XBridge CI 8 column, 5muiotaeta, 19x100 mm, gradient ranges from 10 initial to 60-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min, 8 min run time] to provide the Examplesl65-190. Examples 191-194 were repurified using the following conditions: [Waters Sunfire CI 8 column, 5muetaiota, 19x100 mm, gradient ranges of 10% initial to 70-95% MeCN (0.1% TFA) in water (0.1% TFA) 25 mL/min, 8 min run time]. Example 195 was purified using the following condition: [Waters Sunfire CI 8 column, 5muetaalpha, 19x100 mm, gradient 10% to 50% MeCN (0.1% formic acid) in water (0.1 % formic acid) 25 mL/min, 8 min run time]. Table 11: Parallel preparation of Examples 165-195.

Reference： [1]Patent: WO2014/137723,2014,A1 .Location in patent: Page/Page column 75

11
[ 233278-56-3 ]
C₂₁H₂₆ClFN₄O₂Si [ No CAS ]
C₂₆H₃₃FN₈O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 110℃; for 3h;	To a set of vials containing the chloropyrimidine core from Scheme H (25 mg, 0.056 mmol) in DMSO (0.3 mL) was individually added the requisite amine (0.067 mmol) and diisopropylethylamine (0.039 mL, 0.223 mmol). The vials were capped and the mixtures were heated to 110C with stirring for 3 hours. The mixtures were cooled to RT. Water (2 mL) was added to each vial. The aqueous phase from each vial was extracted with DCM (2 x 1 mL). The organic layers from each vial were transferred to a clean vial and the solvent was removed in vacuo. To each vial was then added THFMeOH (1 :3, 1 mL) followed by HC1 (4 N in dioxane, 0.20 mL, 0.80 mmol). The vials were capped and the solutions were heated to 70C for 0.5 h. The solutions were allowed to cool to RT and the solvent was then removed from the vials in vacuo. Each crude product was redissolved in 1 mL of DMSO and filtered. The crude products (excluding Example 195) were purified by mass triggered HPLC using the following conditions: [Waters XBridge CI 8 column, 5muiotatauiota, 19x100 mm, gradient ranges from 10 initial to 60-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min, 8 min run time] to provide the Examplesl65-190. Examples 191-194 were repurified using the following conditions: [Waters Sunfire CI 8 column, 5muiotaeta, 19x100 mm, gradient ranges of 10% initial to 70-95% MeCN (0.1% TFA) in water (0.1% TFA) 25 mL/min, 8 min run time]. Example 195 was purified using the following condition: [Waters Sunfire CI 8 column, 5muiotaeta, 19x100 mm, gradient 10% to 50% MeCN (0.1% formic acid) in water (0.1 % formic acid) 25 mL/min, 8 min run time]

Reference： [1]Patent: WO2014/134774,2014,A1 .Location in patent: Page/Page column 74

12
[ 233278-56-3 ]
[ 104392-69-0 ]
(S)-N-((3-(4-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2nd generation ruphos precatalyst; caesium carbonate; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	To a solution of (S)-N-((3 -(4-bromophenyl)-2-oxooxazolidin-5 - yl)methyl)acetamide (100.0 mg, 0.319 mmol), 5 ,6,7,8-tetrahydro-[ 1 ,2,4]triazolo[ 1 ,5-a]pyrazine (150.0 mg, 1.208 mmol) and Cs2CO3 (312.0 mg, 0.958 mmol) in 1,4-Dioxane (2 mL) was added 2nd generation ruphos precatalyst (12.4 mg, 0.0 16 mmol) under N2 atmosphere. The mixturewas stirred at 100C for 16 hours. The reaction mixture was concentrated to give a residuewhich was purified by reverse phase prep-HPLC to give (S)-N-((3-(4-(5,6-dihydro-[1,2 ,4]triazolo[ 1,5 -a]pyrazin-7(8H)-yl)phenyl)-2-oxooxazolidin-5 -yl)methyl)acetamide as solid. MS(ESI) m/z: 357.1 [M+Hj.

Reference： [1]Patent: WO2017/66964,2017,A1 .Location in patent: Page/Page column 48; 49

13
[ 233278-56-3 ]
2-(5-{2-[(2,3-dihydro-1H-inden-2-yl)amino]pyrimidin-5-yl}-1,3,4-oxadiazol-2-yl)acetic acid [ No CAS ]
2-(5-{2-[(2,3-dihydro-1H-inden-2-yl)amino]pyrimidin-5-yl}-1,3,4-oxadiazol-2-yl)-1-{5H,6H,7H,8H-[1,2,4]triazolo[1,5-a]pyrazin-7-yl}ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;Inert atmosphere;	The compound 41-a was used in place of the compound im-7 according to the same procedure as in Example 6-1 to give the title compound 41.

Reference： [1]Patent: KR101798840,2017,B1 .Location in patent: Paragraph 0808-0809; 0826-0827; 0896-0897; 0902-0903

14
[ 233278-56-3 ]
2-bromo-N-[1-(1H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide [ No CAS ]
2-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazin-7-yl)-N-[1-(1H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos; In 1,4-dioxane; at 100℃; for 3h;	To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.20 g, 0.49 mmol) and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[1 ,5- a]pyrazine (0.07 g, 0.59 mmol) in dioxane (5 ml_), CS2CO3 (0.24 g, 0.73 mmol) and RuPhos (0.05 g, 0.10 mmol) was added. The reaction mixture was purged with argon for 20 min followed by addition of Pd2(dba)3 (0.05 g, 0.05 mmol) and again purged with argon for 20 min. The reaction mixture was heated at 100C for 3h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was filtered through Celite, washed with 5% MeOH in DCM (30 ml_). The organic layer was separated, washed with H2O15 ml_), brine (15 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 1 to 4% MeOH in DCM) and prep HPLC to afford 2-(6,8- dihydro-5H-[1 ,2,4]triazolo[1 ,5-a]pyrazin-7-yl)-N-[1-(1 H-indol-3- ylmethyl)pentyl]thiazole-5-carboxamide (0.04 g, 18%) as off-white solid.HPLC Purity: 99.4%MS (ESI) m/e [M+H]7Rt/%: 450.00/2.58/97.4% 1H NMR (400 MHz, DMSO-d6) delta 0.82 (t, J=6.85 Hz, 3H) 1.12 - 1.36 (m, 4H) 1.42 - 1.65 (m, 2H) 2.82-2.94 (m, 2H) 3.99 - 4.18 (m, 3H) 4.30 (t, J=5.14 Hz, 2H) 4.81 (s, 2H) 6.93 - 6.99 (m, 1 H) 7.04 (t, J=7.58 Hz, 1 H) 7.10 (s, 1 H) 7.31 (d, J=8.31 Hz, 1 H) 7.57 (d, J=7.82 Hz, 1 H) 7.88 (s, 1 H) 8.01 (s, 1 H) 8.06 (d, J=8.80 Hz, 1 H) 10.76 (brs, 1 H).

Reference： [1]Patent: WO2018/138088,2018,A1 .Location in patent: Page/Page column 32; 33

15
[ 233278-56-3 ]
[ 18143-30-1 ]
6-bromo-3-iodo-2-(1H-1,2,3,4-tetrazol-5-yl)benzene-1-sulfonamide [ No CAS ]
[ 824-94-2 ]
[ 147081-49-0 ]
tert-butyl (R)-3-((2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-(5,6-dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate [ No CAS ]
tert-butyl (R)-3-((2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-(5,6-dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A flask was charged with tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate and tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate (REFERENCE EXAMPLE 5) (0.15 g, 0.156 mmol), <strong>[233278-56-3]5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine</strong> (0.039 g, 0.313 mmol), Cs2CO3 (0.153 g, 0.469 mmol) and rac-BINAP-Pd-G3 precatalyst (0.031 g, 0.031 mmol). The vial was sealed, degassed with N2, and filled with DME (1.6 mL). The resulting mixture was heated overnight at 80 C. The reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated and the residue was purified by silica gel column chromatography using (0-10%) MeOH/DCM as the mobile phase to afford the title compound. LC/MS [M+H]+: 956.81.

Reference： [1]Patent: WO2019/135920,2019,A1 .Location in patent: Page/Page column 48

16
[ 233278-56-3 ]
[ 18143-30-1 ]
6-bromo-3-iodo-2-(1H-1,2,3,4-tetrazol-5-yl)benzene-1-sulfonamide [ No CAS ]
[ 824-94-2 ]
[ 147081-49-0 ]
(R)-4-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-N₁-(pyrrolidin-3-yl)-3-(2H-tetrazol-5-yl)benzene-1,2-disulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To the solution of tert-butyl (R)-3-((2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4- (5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate and tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-(1-(4- methoxybenzyl)-1H-tetrazol-5-yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate (70 mg, 0.073 mmol) in DCM (2.5 mL) was added anisole (0.080 mL, 0.732 mmol) and TFA (0.56 mL, 7.32 mmol) at 0 C. The reaction mixture was stirred at 0 C for 30 min. After removing the volatiles under vacuum, the residue was dissolved in TFA (2.24 mL, 29.3 mmol). The resulting mixture was stirred at 80 C for 1.0 h. After removing the volatiles under vacuum the residue was purified by reverse phase HPLC (gradient 3-30% MeCN/water as eluent, 0.1% NH4OH as additive) to give title compound. LC/MS [M+H]+: 496.50.

Reference： [1]Patent: WO2019/135920,2019,A1 .Location in patent: Page/Page column 48

17
[ 233278-56-3 ]
[ 1365060-89-4 ]
C₁₄H₁₃ClN₆OS₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

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