[ CAS No. 6969-71-7 ] {[proInfo.proName]}

Name: 6969-71-7|[1,2,4]Triazolo[4,3-a]pyridin-3(2H)-one|98%
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SKU: A162219
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Quality Control of [ 6969-71-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6969-71-7 ]

SDS Specification

Alternatived Products of [ 6969-71-7 ]

Product Details of [ 6969-71-7 ]

CAS No. :	6969-71-7	MDL No. :	MFCD00022632
Formula :	C₆H₅N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LJRXNXBFJXXRNQ-UHFFFAOYSA-N
M.W :	135.12	Pubchem ID :	81431
Synonyms :

Calculated chemistry of [ 6969-71-7 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.81
TPSA :	50.16 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) :	-7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	0.04
Log Po/w (WLOGP) :	0.02
Log Po/w (MLOGP) :	0.85
Log Po/w (SILICOS-IT) :	0.66
Consensus Log Po/w :	0.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.37
Solubility :	5.78 mg/ml ; 0.0428 mol/l
Class :	Very soluble
Log S (Ali) :	-0.65
Solubility :	30.5 mg/ml ; 0.226 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.59
Solubility :	3.49 mg/ml ; 0.0258 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 6969-71-7 ]

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

Application In Synthesis of [ 6969-71-7 ]

* 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 [ 6969-71-7 ]
Downstream synthetic route of [ 6969-71-7 ]

[ 6969-71-7 ] Synthesis Path-Upstream 1~9

1
[ 109-09-1 ]
[ 563-41-7 ]
[ 6969-71-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sulfuric acid In 2-ethoxy-ethanol for 24 h; Reflux	[1,2,4]Triazolo[4,3-a]pyridin-3-(2H)-one: A mixture of 2-chloropyridine (5.0 g, 44.03 mmol), semicarbazide hydrochloride (9.8 g, 88.06 mmol) and 2-ethoxyethanol (15 mL) was heated to reflux and treated with a solution of conc. sulfuric acid (0.1 mL) in 2-ethoxyethanol (1 mL). The resulting solution was maintained at reflux for 24 hours, cooled to about 60° C. and diluted with water (15 mL). The resulting solid was filtered and washed with water to yield the title product as a pale yellow solid (2.2 g, 51percent). m.p. 235-240° C.; ¹H NMR (300 MHz, DMSO-d₆) δ 6.51-6.60 (m, 1H), 7.05-7.22 (m, 2H), 7.80 (d, J=7.1 Hz, 1H), 12.45 (br, 1H, exchangeable with deuterium oxide); IR (KBr) ν 3173, 3098, 3048, 1717, 1634, 1536, 1348 cm^-1; MS 136 (M+1).
59%	With sulfuric acid In 2-ethoxy-ethanol; water	Procedure 1. 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one A mixture of 50 g. (0.44 mole) of 2-chloropyridine and 98.22 g. (0.88 mole) of semicarbazide hydrochloride in 150 ml. of 2-ethoxyethanol was heated to reflux and then treated with a solution of 1 ml. of concentrated sulfuric acid (36 N) in 5 ml. of 2-ethoxyethanol. The resulting solution was refluxed for 18 hr., cooled to about 60°, and treated with 150 ml. of water. The mixture was stirred, cooled to 0°, and kept 0.5 hr. and the solid was collected on a filter. The solid was washed well with water and dried under reduced pressure, to give 35.0 g (59percent) of product, m.p. 230°-231°, which was sufficiently pure to be used for the next step. Anal. Found: C, 52.96; H, 3.75; N, 30.94.

Reference： [1] Patent: US2009/209550, 2009, A1, . Location in patent: Page/Page column 25-26
[2] Patent: US4254124, 1981, A,

2
[ 4231-61-2 ]
[ 6969-71-7 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 37, p. 4815 - 4818

3
[ 4930-98-7 ]
[ 57-13-6 ]
[ 6969-71-7 ]

Yield	Reaction Conditions	Operation in experiment
15%	at 130℃; for 3 h;	A mixture of crude CAP-004-05-A and urea (1.70 g, 27.50 mmol) was stirred at 130 oc for 3h. The resultant was purified by column chromatography on silica gel (ethylacetate/petroleum ether = 1/10-3/1) to give CAP-004-05 (0.13 g, 15 percent, two steps) as a pale white solid.

Reference： [1] Heterocycles, 2000, vol. 53, # 2, p. 265 - 270
[2] Patent: WO2017/46318, 2017, A1, . Location in patent: Page/Page column 41

4
[ 109-09-1 ]
[ 4426-72-6 ]
[ 6969-71-7 ]

Reference： [1] Patent: US4465683, 1984, A,

5
[ 109-04-6 ]
[ 6969-71-7 ]

Reference： [1] Patent: WO2017/46318, 2017, A1,

6
[ 109-09-1 ]
[ 6969-71-7 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 21, p. 3855 - 3859

7
[ 4930-98-7 ]
[ 6969-71-7 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 21, p. 3855 - 3859

8
[ 51330-53-1 ]
[ 64-19-7 ]
[ 6969-71-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 10, p. 2969 - 2973

9
[ 109-89-7 ]
[ 51330-53-1 ]
[ 685-91-6 ]
[ 6969-71-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 10, p. 2969 - 2973

[ 6969-71-7 ] Synthesis Path-Downstream 1~77

1
[ 541-41-3 ]
[ 6969-71-7 ]
1-ethoxycarbonyl-1,2,4-triazolo<4,3-a>pyridinium-3-olate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

2
[ 98-88-4 ]
[ 6969-71-7 ]
[ 27414-98-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

3
[ 501-53-1 ]
[ 6969-71-7 ]
[ 50739-45-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

4
[ 107-04-0 ]
[ 6969-71-7 ]
[ 137540-94-4 ]

Reference： [1]Journal of medicinal chemistry,1992,vol. 35,p. 189 - 194

5
[ 109-89-7 ]
[ 51330-53-1 ]
[ 685-91-6 ]
[ 6969-71-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

6
[ 75-36-5 ]
[ 6969-71-7 ]
[ 27191-52-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

7
[ 75-44-5 ]
[ 6969-71-7 ]
[ 50993-36-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

8
[ 75-44-5 ]
[ 6969-71-7 ]
[ 50739-46-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

9
[ 131060-08-7 ]
[ 6969-71-7 ]
[ 139477-46-6 ]

Reference： [1]Journal of Pharmaceutical Sciences,1992,vol. 81,p. 99 - 103

10
[ 97634-03-2 ]
[ 6969-71-7 ]
[ 97634-05-4 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1394 - 1398

11
[ 6969-71-7 ]
[ 103-80-0 ]
2-phenylacetyl-1,2,4-triazolo<4,3-a>pyridin-3(2H)-one [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

12
[ 51330-53-1 ]
[ 64-19-7 ]
[ 6969-71-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

13
[ 4930-98-7 ]
[ 57-13-6 ]
[ 6969-71-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	In neat (no solvent); for 0.0138889h;Microwave irradiation;	Firstly, 500 mg (4.58 mmol) g of 2-hydrazinopyridine (7) and 275 mg (4.58 mmol) or 550 mg(9.16 mmol) of urea were placed in a conical flask. Reactions were carried out under microwave radiation. The progress of the reaction was monitored by TLC (chloroform-methanol 9:1). After 50 s,15 cm3 of water was added to the mixture, after which the resulting product was filtered o on aBuechner funnel. The product was obtained with eciency 49% in an equimolar reaction and 75%by reaction with a two fold molar excess of urea; Rf = 0.62, HPLC 97.9% (reaction with molar excess),tM 1.95 min.
15%	at 130℃; for 3h;	A mixture of crude CAP-004-05-A and urea (1.70 g, 27.50 mmol) was stirred at 130 oc for 3h. The resultant was purified by column chromatography on silica gel (ethylacetate/petroleum ether = 1/10-3/1) to give CAP-004-05 (0.13 g, 15 %, two steps) as a pale white solid.

Reference： [1]Molecules,2019,vol. 24
[2]Heterocycles,2000,vol. 53,p. 265 - 270
[3]Patent: WO2017/46318,2017,A1 .Location in patent: Page/Page column 41

14
[ 100-39-0 ]
[ 6969-71-7 ]
[ 42238-98-2 ]
[ 4231-61-2 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 265 - 270

15
[ 6969-71-7 ]
[ 74-88-4 ]
[ 4231-60-1 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 265 - 270

16
[ 6969-71-7 ]
[ 74-88-4 ]
C₇H₇N₃O [ No CAS ]
[ 4231-60-1 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 265 - 270

19
[ 6969-71-7 ]
(1S,2R,5S)-2-(4'-Chloro-biphenyl-4-ylsulfanyl)-5-methanesulfonyloxymethyl-cyclopentanecarboxylic acid tert-butyl ester [ No CAS ]
2-(4'-chloro-biphenyl-4-ylsulfanyl)-5-(3-oxo-[1,2,4]triazolo[4,3-<i>a</i>]pyridin-2-ylmethyl)-cyclopentanecarboxylic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3840 - 3852

20
[ 6969-71-7 ]
(1S,2R,5S)-2-(4'-Chloro-biphenyl-4-ylsulfanyl)-5-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-ylmethyl)-cyclopentanecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3840 - 3852

21
[ 109-04-6 ]
<1,3>dioxolan-2-ylidene-malonodinitrile [ No CAS ]
[ 6969-71-7 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 265 - 270

22
[ 6969-71-7 ]
1-(N-2-pyridylbenzylamino)-3,4,5,6-tetra(methoxycarbonyl)-pyrid-2-one [ No CAS ]

Reference： [1]Heterocycles,2000,vol. 53,p. 265 - 270

23
[ 6969-71-7 ]
[ 50739-44-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

24
[ 6969-71-7 ]
[ 50739-45-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

25
[ 6969-71-7 ]
[ 51330-53-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

26
[ 6969-71-7 ]
2-phenylacetyl-1,2,4-triazolo<4,3-a>pyridin-3(2H)-one [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

27
[ 6969-71-7 ]
2-benzyloxycarbonyl-1,2,4-triazolo<4,3-a>pyridin-3(2H)-one [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

28
[ 6969-71-7 ]
1-benzoyl-1,2,4-triazolo<4,3-a>pyridinium-3-olate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

29
[ 6969-71-7 ]
[ 88754-51-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

30
[ 6969-71-7 ]
C₉H₆Cl₃N₃O₃ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

31
[ 6969-71-7 ]
[ 89762-47-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

32
[ 6969-71-7 ]
C₁₄H₁₀N₄O₅ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

33
[ 6969-71-7 ]
C₂₀H₁₅N₃O₃ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2974 - 2980

34
[ 6969-71-7 ]
1-<N-(benzyloxycarbonyl)glycyl>-1,2,4-triazolo<4,3-a>pyridinium-3-olate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 2969 - 2973

35
[ 6969-71-7 ]
[ 137540-95-5 ]

Reference： [1]Journal of medicinal chemistry,1992,vol. 35,p. 189 - 194

36
[ 109-70-6 ]
[ 6969-71-7 ]
[ 19666-40-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 0.0222222h;Microwave irradiation;	General procedure: Firstly, 1.35 g (0.01 mol) of 1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one (1), 2.50 cm3 (26 mmol, 4.09 g)of 1-bromo-3-chloropropane (2a)/2.65 cm3 (0.026 mol, 5.25 g) of 1,3-dibromopropane (2b), 320 mg(0.001 mol) of TBAB, 4.14 g (0.03 mol) of K2CO3, and the appropriate amount of acetonitrile (6, 3,0.75, or 0.4 cm3)/DMF (5 cm3) were placed in a conical flask, after which the mixture was subjected to microwave radiation. The progress of the reaction was monitored by TLC (chloroform-methanol 9:1).The reaction times are summarized in Table 1. After the reaction, about 50 cm3 of water was added and the resulting product was filtered o on a Buechner funnel. The reaction yields are summarized inTable 1. The purity of the product obtained with the highest eciency (Y = 92%) was confirmed usingHPLC 99.3% tM = 3.43 min.
70%	With potassium carbonate; In acetonitrile; for 8h;Heating / reflux;	[0181] 2-(3-chloropropyl)-1,2,4-triazo[4,3-a]pyridin-3(2H)-one(7. A mixture of 1,2,4-triazo[4,3-a]pyridin-3(2H)-one (6), 1.35 g, 10 mmol), 1-bromo-3-chloropropane (4.13 g, 26 mmol) and potassium carbonate (2.07 g, 15 mmol) in MeCN (15 mL) was refluxed for 8 h. After removal of the insoluble material by filtration, the filtrate was concentrated and the residue was extracted with CHCl3 (150 mL). After evaporation of the solvent, the residual material was purified by column chromatography (EtOAc/Heptane, 1:2) to give 2-(3-chloropropyl)-1,2,4-triazo[4,3-a]pyridin-3(2H)-one, compound 7 (1.47 g, 70%). Compound 7 was confirmed by 1H-NMR and LC-MS.

Reference： [1]Molecules,2019,vol. 24
[2]Patent: US2003/232839,2003,A1 .Location in patent: Page 24; 26

37
[ 29559-55-5 ]
[ 6969-71-7 ]
[ 581778-40-7 ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 150℃; for 48h;	[0187] Compound 3. A mixture of 1,2,4-triazolo(4,3-a)pyridin-3(2H)-one (11.2 g, 82.88 mmol) (1), 1,3-dichloro-2,2-dimethyl propane (2), and K2CO3 (23.0 g, 21.71 mmol.) in DMF (100 mL) was stirred at 150 C. for 48 hours. Product 3 (5.4 g, 27% yield) was isolated by silica gel column purification and confirmed by 1H-NMR, LC-MS.

Reference： [1]Patent: US2003/232839,2003,A1 .Location in patent: Page 25; 27

38
[ 6969-71-7 ]
[ 540-51-2 ]
[ 56654-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 18h;Heating / reflux;	Toluene-4-sulfonic acid 2-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl)-ethyl ester was prepared starting from 1,2,4-triazolo pyridinone. 1,2,4-triazolo pyridinone (1.485 g, 10 mmol) was dissolved in 220 ml acetone. The solution under nitrogen was then added 17 gram potassium carbonate and 1.364 bromoethanol(1.1 eq). The mixture was refluxed under nitrogen for 18 hours. It was then cooled down to room temperature and poured into about 300 ml water and extracted with ethyl acetate (2×20 ml). The combined organic layers were dried over magnesium sulfate and filtered and concentrated. Flash column chromatography using 1:1 mixture of hexane and ethyl acetate yielded 2.5 gram crude product. The crude compound was dissolved in a 1:1 mixture of THF/DMF. The solution was put under nitrogen and added 800 mg NaH(60%, 20 mmol). The mixture was stirred under nitrogen for half an hour. Tosyl chloride 2.1 gram (11 mmol, 1 eq) was next added to the reaction media and the resulting solution was heated at 50 C. for 18 hours. Then it was cooled down to room temperature and methanol was added under nitrogen until no bubbles observed. It was then poured into about 300 ml water and extracted with ethyl acetate (2×200 ml). The combined organic layers were dried over magnesium sulfate and filtered and concentrated. Flash column chromatography using 70% ethyl acetate/hexane and yielded 834 mg of product (23%). [0129] Toluene-4-sulfonic acid 2-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl)-ethyl ester 166 mg (0.5 mmol) was dissolved in 50 ml DMSO. To this solution was added 99 mg of 3-(1,2,3,6-Tetrahydro-pyridin-4-yl)-1H-indole, (1 eq, 0.5 mmol) and 5 ml triethyl amine. The reaction media was heated under nitrogen at 85 C. for 18 hours. It was then cooled down to room temperature and poured into about 300 ml water and extracted with ethyl acetate (2×200 ml). The combined organic layers were dried over magnesium sulfate and filtered and concentrated. Flash column chromatography using ethyl acetate and 20% methanol/ethyl acetate yielded 54 mg product (30%). mp: 170.4 C.; M+: 360.1; H-NMR: 8.28 (b, 1H, NH), 7.88 (d, 1H), 7.55(d, 1H), 7.30(d, 1H), 7.14(m, 5H), 6.47(m, 1H), 6.19 (m, 1H), 4.25 (m, CH2), 3.35 (d, CH2), 3.00 (t, CH2) 2.86 (t, CH2), 2.60(m, CH2).

Reference： [1]Patent: US2004/204402,2004,A1 .Location in patent: Page/Page column 13

39
[ 109-09-1 ]
[ 563-41-7 ]
[ 6969-71-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sulfuric acid; In 2-ethoxy-ethanol; for 24h;Reflux;	[1,2,4]Triazolo[4,3-a]pyridin-3-(2H)-one: A mixture of 2-chloropyridine (5.0 g, 44.03 mmol), semicarbazide hydrochloride (9.8 g, 88.06 mmol) and 2-ethoxyethanol (15 mL) was heated to reflux and treated with a solution of conc. sulfuric acid (0.1 mL) in 2-ethoxyethanol (1 mL). The resulting solution was maintained at reflux for 24 hours, cooled to about 60 C. and diluted with water (15 mL). The resulting solid was filtered and washed with water to yield the title product as a pale yellow solid (2.2 g, 51%). m.p. 235-240 C.; 1H NMR (300 MHz, DMSO-d6) delta 6.51-6.60 (m, 1H), 7.05-7.22 (m, 2H), 7.80 (d, J=7.1 Hz, 1H), 12.45 (br, 1H, exchangeable with deuterium oxide); IR (KBr) nu 3173, 3098, 3048, 1717, 1634, 1536, 1348 cm-1; MS 136 (M+1).
48%	With sulfuric acid; In 2-ethoxy-ethanol; for 0.0333333h;Microwave irradiation;	Firstly, 5.00 g (44 mmol) of 2-chloropyridine (6a), 9.81 g (88 mmol) of semicarbazide hydrochloride,15 cm3 of 2-ethoxyethanol, and 0.1 cm3 of concentrated sulfuric acid were placed in a conical flask.Reactions were carried out under microwave radiation. The progress of the reaction was monitored byTLC (eluent chloroform-methanol 9:1). After 2 min, the reaction mixture was cooled to about 60 Cand 15 cm3 of water was added. The precipitate was filtered on a Buechner funnel and washed withabout 50 cm3 of water. Y = 48%.
35.0 g (59%)	With sulfuric acid; In 2-ethoxy-ethanol; water;	Procedure 1. 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one A mixture of 50 g. (0.44 mole) of 2-chloropyridine and 98.22 g. (0.88 mole) of semicarbazide hydrochloride in 150 ml. of 2-ethoxyethanol was heated to reflux and then treated with a solution of 1 ml. of concentrated sulfuric acid (36 N) in 5 ml. of 2-ethoxyethanol. The resulting solution was refluxed for 18 hr., cooled to about 60, and treated with 150 ml. of water. The mixture was stirred, cooled to 0, and kept 0.5 hr. and the solid was collected on a filter. The solid was washed well with water and dried under reduced pressure, to give 35.0 g (59%) of product, m.p. 230-231, which was sufficiently pure to be used for the next step. Anal. Found: C, 52.96; H, 3.75; N, 30.94.

Reference： [1]Patent: US2009/209550,2009,A1 .Location in patent: Page/Page column 25-26
[2]Molecules,2019,vol. 24
[3]Patent: US4254124,1981,A

40
[ 109-09-1 ]
[ 4426-72-6 ]
[ 6969-71-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In 2-ethoxy-ethanol; water;	1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one A mixture of 50 g. (0.44 mole) of 2-chloropyridine and 98.22 g. (0.88 mole) of semicarbazide hydrocloride in 150 ml. of 2-ethoxyethanol was heated to reflux and then treated with a solution of 1 ml. of concentrated sulfuric acid (36 N) in 5 ml. of 2-ethoxyethanol. The resulting solution was refluxed for 18 hr., cooled to about 60, and treated with 150 ml. of water. The mixture was stirred, cooled to 0, and kept 0.5 hr. and the solid was collected on a filter. The solid was washed well with water and dried under reduced pressure, to give 35.0 g. (59%) of product, m.p. 230-231, which was sufficiently pure to be used for the next step. Anal. Found: C, 52.96; H, 3.75; N, 30.94.

Reference： [1]Patent: US4465683,1984,A

41
[ 1084812-30-5 ]
[ 6969-71-7 ]
[ 1084811-05-1 ]

Yield	Reaction Conditions	Operation in experiment
46 - 64%	With potassium phosphate; N,N`-dimethylethylenediamine;copper(l) iodide; In 1,4-dioxane; at 110℃; for 16h;Product distribution / selectivity;	To a solution of the bromide (0.3 g, 0.8 mmol, partially pure) from step A in 1,4-dioxane (1 mL) were added pyridazin-3(2H)-one (94 mg, 0.98 mmol), lambda/,N'-dimethylethylenediamine (35 muL, 0.33 mmol), and potassium phosphate (0.35 g, 1.63 mmol). The mixture was purged with argon, and copper (I) iodide (31 mg, 0.16 mmol) was added to it. The reaction was heated at 110 0C for 16 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, washed with water and brine, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by reverse phase semi- preparative etaPLC (5% B to 50% B over 35 min; A = 95:5 water/acetonitrile + 0.05% <n="96"/>TFA, B = 95:5 acetonitrile/water + 0.05% TFA), and conversion into the corresponding free base using 2N sodium carbonate gave the coupled product (202 mg, 64%) as a pale yellow foam: 1H NMR (CDCl3, 500 MHz) delta 7.89 (dd, J= 3.8, 1.7 Hz, IH), 7.51-7.48 (m, 2H), 7.40 (d, J= 8.2 Hz, IH), 7.27-7.22 (m, 2H), 7.05-7.03 (m, IH), 6.46-6.40 (m, 3H), 5.38 (dd, J= 9.2, 1.1 Hz, IH), 4.05-3.79 (m, 2H), 3.37- 3.26 (m, IH), 3.10-2.95 (m, IH), 2.32 (s, 3H), 2.26-2.05 m, 2H)Example 43 - Preparation of (+)- and (-)-2-(5-(3,5-difluorophenoxy)-2-methyl- 2,3,4,5-tetrahydro- lH-benzo [c] azepin-8-yl)- [ 1 ,2,4] triazolo [4,3- fl]pyridin-3(2H)-one, tartrate salt[0245] Step A: To a solution of the bromide (0.3 g, 0.8 mmol, partially pure) from Step A in Example 36 in 1,4-dioxane (1 mL) were added [l,2,4]triazolo[4,3- alpha]pyridin-3(2H)-one (0.13 g, 0.98 mmol), lambda/,N'-dimethylethylenediamine (35 muL, 0.33 mmol), and potassium phosphate (0.35 g, 1.63 mmol). The mixture was purged with argon, and copper (I) iodide (31 mg, 0.16 mmol) was added to it. The reaction was heated at 110 0C for 16 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, washed with water and brine, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by reverse phase semi-preparative etaPLC (5% B to 50% B over 35 minutes; A = 95:5 water/acetonitrile + 0.05% TFA, B = 95:5 acetonitrile/water + 0.05% TFA), and conversion into the corresponding free base using 2N sodium carbonate gave the coupled product (158 mg, 46%) as a yellow foam, which was resolved by preparative chiral etaPLC (CetaIRALCEL OJ column, using 60:40:0.1 heptanes/ethanol/diethylamine as the eluent) to give enantiomer A and enantiomer B.

Reference： [1]Patent: WO2008/141082,2008,A1 .Location in patent: Page/Page column 94-95; 105

42
[ 349097-88-7 ]
[ 6969-71-7 ]
[ 53689-32-0 ]

Yield	Reaction Conditions	Operation in experiment
30%	With tetrabutylammomium bromide; potassium hydroxide; In toluene; at 110℃; for 16h;	2-(3-(4-(3-Chlorophenyl)piperazin-1-yl)-3-oxopropyl)<strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong>: A mixture of 3-chloro-1-[4-(3-chlorophenyl)piperazin-1-yl]propan-1-one (2.13 g, 7.4 mmol), [1,2,4]triazolo[4,3-a]pyridin-3-(2H)-one (1.0 g, 7.4 mmol), potassium hydroxide (0.4 g, 7.4 mmol), tetra-n-butylammonium bromide (2.38 g, 7.4 mmol), and toluene (20 mL) was heated at about 110 C. for about 16 hours. Standard extractive work up provided a crude residue which was purified by silica gel column chromatography (3% methanol in chloroform) to yield the title product as an off-white solid (0.850 g, 30%). 1H NMR (300 MHz, CDCl3) delta 2.95 (t, J=7.5 Hz, 2H), 3.12-3.18 (m, 4H), 3.57-3.63 (m, 2H), 3.75-3.80 (m, 2H), 4.39 (t, J=7.4 Hz, 2H), 6.46-7.21 (m, 7H), 7.76 (d, J=6.9 Hz, 1H); IR (KBr) nu 3045, 1709, 1626, 1469,1435, 1220 cm-1; MS 386, 388 [(M+1), (M+3)].

Reference： [1]Patent: US2009/209550,2009,A1 .Location in patent: Page/Page column 26-27

43
[ 6969-71-7 ]
[ 6001-87-2 ]
[ 1039852-17-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3h;	Methyl 3-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propanoate: A mixture of [1,2,4]triazolo[4,3-a]pyridin-3-(2H)-one (5.0 g, 37.0 mmol), methyl 3-chloropropionate (6.7 g, 55.5 mmol), finely powdered cesium carbonate (30.1 g, 92.6 mmol) and dimethylformamide (40 mL) was heated at about 90 C. for about 3 hours. Standard extractive work up yielded the title compound as a cream colored solid (6.1 g, 74%). m.p. 95-99 C.; 1H NMR (400 MHz, CDCl3) delta 2.89 (t, J=7.0 Hz, 2H), 3.71 (s, 3H), 4.32 (t, J=7.0 Hz, 2H), 6.45-6.51 (m, 1H), 7.06-7.09 (m, 2H), 7.75 (d, J=7.2 Hz, 1H); IR (KBr) nu 3399, 3103, 3043, 2953, 1701, 1640, 1542, 1445, 1306 cm-1; MS222 (M+1).

Reference： [1]Patent: US2009/209550,2009,A1 .Location in patent: Page/Page column 27

44
[ 1181578-67-5 ]
[ 6969-71-7 ]
[ 1181577-82-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃;	2-(3-(4-(3-Chlorophenyl)piperazin-1-yl)propyl-1,1-d2)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)one hydrochloride: The procedure of Example 2, step 5 was followed, but substituting 2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl-1,1-d2)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)one for 2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl-3,3-d2)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)one hydrochloride. The title compound was obtained as an off-white solid (0.200 g, 91%). m.p. 228-230 C.; 1H NMR (400 MHz, D2O) delta 2.27-2.34 (m, 2H), 3.07-3.31 (m, 6H), 3.62-3.88 (m, 4H), 6.74-7.38 (m, 7H), 7.81 (d, J=7.0 Hz, 1H); IR (KBr) nu 3393, 2456, 1701, 1641, 1594, 1442, 1358 cm-1; MS 374, 376 [(M+1)-HCl, (M+3)-HCl].

Reference： [1]Patent: US2009/209550,2009,A1 .Location in patent: Page/Page column 29-30

45
[ 64528-94-5 ]
[ 6969-71-7 ]
[ 1181578-69-7 ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium carbonate; In acetonitrile; at 60℃; for 18h;	2-(3-Bromopropyl-1,1,3,3-d4)-[1,2,4}triazolo[4,3-a]pyridin-3(2H)-one: A mixture of [1,2,4]triazolo[4,3-a]pyridin-3-(2H)-one (0.300 g, 2.22 mmol), 1,3-dibromopropane-1,1,3,3-d4 (0.453 g, 2.20 mmol), potassium carbonate (1.220 g, 8.88 mmol) and acetonitrile (10 mL) was heated at about 60 C. for about 18 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo, and the resulting crude residue was purified by column chromatography on neutral alumina (15% ethyl acetate in petroleum ether) to yield the title product as an off-white solid (0.180 g, 31%). 1H NMR (400 MHz, CDCl3) delta 2.39 (s, 2H), 6.47-6.53 (m, 1H), 7.07-7.12 (m, 2H), 7.77 (d, J=7.2 Hz, 1H); IR (KBr) nu 3094, 3045, 1710, 1637, 1531, 1437, 1348 cm-1; MS 260, 262 [(M+1), (M+3)].

Reference： [1]Patent: US2009/209550,2009,A1 .Location in patent: Page/Page column 30

46
[ 6969-71-7 ]
[ 109-64-8 ]
2-(3-bromopropyl)[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 0.0333333h;Microwave irradiation;	General procedure: Firstly, 1.35 g (0.01 mol) of 1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one (1), 2.50 cm3 (26 mmol, 4.09 g)of 1-bromo-3-chloropropane (2a)/2.65 cm3 (0.026 mol, 5.25 g) of 1,3-dibromopropane (2b), 320 mg(0.001 mol) of TBAB, 4.14 g (0.03 mol) of K2CO3, and the appropriate amount of acetonitrile (6, 3,0.75, or 0.4 cm3)/DMF (5 cm3) were placed in a conical flask, after which the mixture was subjected to microwave radiation. The progress of the reaction was monitored by TLC (chloroform-methanol 9:1).The reaction times are summarized in Table 1. After the reaction, about 50 cm3 of water was added and the resulting product was filtered o on a Buechner funnel. The reaction yields are summarized inTable 1. The purity of the product obtained with the highest eciency (Y = 92%) was confirmed usingHPLC 99.3% tM = 3.43 min.

Reference： [1]Molecules,2019,vol. 24

47
[ 632-02-0 ]
[ 6969-71-7 ]
[ 19666-40-1 ]

Yield	Reaction Conditions	Operation in experiment
58%		EXAMPLE 22 2-{3-[4-(1H-Indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one 2-(3-Chloro-propyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one was synthesised starting from 1,2,4-triazolo pyridinone. 1,2,4-triazolo pyridinone, 1.35 g(10 mmol) was dissolved in 100 ml DMF. The solution under nitrogen was then added 440 mg NaH(60%, 1.1 eq). The mixture was stirred under nitrogen for half an hour. 3-chloropropanol tosylate was then added all at once and the reaction media was heated at 50 C. for 4 hours. It was then cooled down to room temperature and poured into about 300 ml water and extracted with ethyl acetate (2200 ml). The combined organic layers were dried over magnesium sulfate and filtered and concentrated. Flash column chromatography using 1:1 mixture of hexane and ethyl acetate yielded 1.216 gram product (58%). 2-(3-Chloro-propyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one 211 mg (1 mmol) was loaded into a round bottomed flask, followed by 396 mg (2 eq) of 3-(1,2,3,6-Tetrahydro-pyridin-4-yl)-1H-indole, 1.0 gram of potassium iodide, 1.0 gram of potassium carbonate, 100 ml acetone. The mixture was stirred under nitrogen for 18 hours. It was then poured into about 300 ml water and extracted with ethyl acetate (2200 ml). The combined organic layers were dried over magnesium sulfate and filtered and concentrated. Flash column chromatography using 10% ~100% ethyl acetate/hexane and yielded 220 mg of product (59%). mp: 173.3 C. M+: 374.0; (300 MHz, CDCl3): 8.60 (s, 1H, NH), 7.90 (d, 1H), 7.75(d, 1H), 7.34(d, 1H), 7.11(m, 5H), 6.44(m, 1H), 6.16(s, 1H), 4.12 (t, CH2), 3.22 (d, CH2), 2.70 (t, CH2) 2.60(m, 4H), 2.17 (t, CH2).

Reference： [1]Patent: US2004/204402,2004,A1 .Location in patent: Page/Page column 12-13

48
[ 4231-61-2 ]
[ 6969-71-7 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 4815 - 4818

49
[ 922711-93-1 ]
[ 6969-71-7 ]
3,4-dichloro-N-{5-chloro-2-[(3-oxo[1,2,4]triazolo[4.3-a]pyridin-2(3H)-yl)methyl]phenyl}benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To the commercially available [112,4]triazolo[4,3-a]pyridin-3(2H)-one (27 mg, 0.20 mmol) and 18-crown-6 ether (55 mg, 0.21 mmol) in anhydrous 1 ,4-dioxan (1 ml.) was added a 1 M solution of potassium te/t-butoxide in tetrahydrofuran (210 mul_, 0.21 mmol) . The mixture was stirred at room temperature for 15 minutes and then 1 ml_ of a solution of 3,4-dichloro-N-[5-chloro-2-(chloromethyl)phenyl]benzenesulfonamide (655 mg, 1.7 mmol) in anhydrous 1 ,4-dioxane (17 mL) was added. The mixture was heated at 60 0C for 15 hours and then left to cool to room temperature. The solvent was removed under reduced pressure and the residue dissolved in dimethyl sulphoxide (0.5 mL) and then purified by mass directed autoprep to give 3,4-dichloro-N-{5-chloro-2-[(3- oxo[1 ,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl]phenyl}benzenesulfonamide as a white solid (6.6mg). HPLC Rt = 3.23 minutes; m/z [M+H]+ = 483. 1H NMR (d6-DMSO) delta 7.85 (m, 3H), 7.63 (d, 1 H), 7.28 (d, 1 H), 7.24 (t, 1 H), 7.17 (d, 1 H), 7.09 (d, 1 H), 6.99 (s, 1 H), 6.63 (t, 1 H)1 5.00 (S1 2H).

Reference： [1]Patent: WO2007/14054,2007,A2 .Location in patent: Page/Page column 66-67

50
(3R,4R,5R,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
[ 6969-71-7 ]
[ 1334297-40-3 ]

Reference： [1]Patent: US2011/237527,2011,A1

51
(3R,4R,5R,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
[ 6969-71-7 ]
(3R,4R,5R,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 15h;Inert atmosphere;	To a solution of (3R,4R,5R,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.21 g, 0.43 mmol) and <strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong> (67.4 mg, 0.50 mmol) in tetrahydrofuran (20 mL) were added triphenylphosphine (0.17 g, 0.65 mmol) and diethyl azodicarboxylate (0.11 g, 0.65 mmol) under nitrogen. The reaction solution was stirred at room temperature for 15 hours and then it was quenched with aqueous ammonium chloride solution, extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was partially purified by flash column chromatography (eluent: hexanes/ethyl acetate 95:5 to 25:75) to give (3R,4R,5R,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate (0.36 g, partial pure), which was used in the next step without further purification.

Reference： [1]Patent: US2011/237527,2011,A1 .Location in patent: Page/Page column 17

52
(2S,3R,4R,5R)-2-(3-(bromomethyl)-4-chlorophenyl)-3,4,5-tris(4-methoxybenzyloxy)-6-((4-methoxybenzyloxy)methyl)tetrahydro-2H-pyran [ No CAS ]
[ 6969-71-7 ]
C₅₁H₅₂ClN₃O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of sodium hydride (95.5 mg, 0.71 mmol) in DMF (2.0 mL) at 0 C. under nitrogen was added <strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong> (33.6 mg, 0.84 mmol). The resultant solution was stirred at 0 C. for 5 minutes, then a solution of the product from step E (0.20 g, crude). The reaction mixture was let to warm to room temperature and stirred for 60 hours. Reaction was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude material obtained was then used in the next step without purification: LC-ESI MS m/z 902 [M+H]+.

Reference： [1]Patent: US2011/237527,2011,A1 .Location in patent: Page/Page column 18

53
[ 1360440-46-5 ]
[ 6969-71-7 ]
[ 1360440-43-2 ]

Yield	Reaction Conditions	Operation in experiment
19%	With potassium phosphate; copper(l) iodide; L-proline; In 1,4-dioxane; dimethyl sulfoxide; at 120℃; for 16h;	Step B: A mixture of the 8-bromo-ethanobenzazepine (0.28 g, 0.77 mmol) from Step A above, <strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong> (0.21 g, 1.5 mmol), potassium phosphate (0.49 g, 2.3 mmol), dimethyl ethylenediamine (0.066 mL, 0.62 mmol), copper iodide (73 mg, 0.39 mmol), L-proline (71 mg, 0.62 mmol) in 1,4-dioxane (8 mL) and DMSO (8 mL) was stirred at 120 C. for 16 h. The reaction was then cooled to rt, diluted with dichloromethane and filtered through a pad of celite. The filtrate obtained was concentrated in vacuo and the resultant residue was diluted with ethyl acetate, washed with water (2*) and brine, dried over sodium sulfate and concentrated in vacuo. The crude product obtained was purified by flash column chromatography (ethyl acetate to 91:8.1:0.9 ethyl acetate/methanol/concentrated ammonium hydroxide), then preparative thin layer chromatography (93:6.3:0.7 ethyl acetate/methanol/concentrated ammonium hydroxide, followed by 93:6.3:0.7 dichloromethane/methanol/concentrated ammonium hydroxide) to give 2-(5-(4-chlorophenyl)-2,5-ethano-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)-<strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong> (60.8 mg, 19%).

Reference： [1]Patent: US2012/46271,2012,A1 .Location in patent: Page/Page column 33

54
[ 57205-09-1 ]
[ 6969-71-7 ]
C₁₅H₁₉N₃O₄ [ No CAS ]
C₁₅H₁₉N₃O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 9973 - 9978

55
[ 142944-48-7 ]
[ 6969-71-7 ]
[ 19794-93-5 ]

Yield	Reaction Conditions	Operation in experiment
65%		1-(3-bromopropyl)-4-(3-chlorophenyl)piperazine (6) (0.135 g, 0.43 mmol) was added to a boiling solution of dioxane (0.807 ml). Sodium hydride (0.6 mmol) was added slowly and the mixture was refluxed for 1 h. <strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong> (7) (0.068 mL, 0.5 mmol) was added to the reaction mixture and refluxed for 20 h. The reaction mixture was cooled and diluted with equal volume of diethyl ether. The organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (0:100/ hexane: ethyl acetate) to afford the coupling product as brown oil.Brown oil (65% yield); Rf = 0.01 (4: 1 hexane/ethyl acetate)

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5332 - 5334

56
[ 866605-99-4 ]
[ 6969-71-7 ]
[ 1334297-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 15h;Inert atmosphere;	To a solution of alcohol 13 (0.21g, 0.43mmol) and <strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong> (14, R=H, 67.4mg, 0.50mmol) in tetrahydrofuran (20mL) were added triphenylphosphine (0.17g, 0.65mmol) and diethyl azodicarboxylate (0.11g, 0.65mmol) under nitrogen. The reaction solution was stirred at room temperature for 15h, then it was quenched with aqueous ammonium chloride solution and extracted with EtOAc. The organic extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was first purified by flash column chromatography (eluent: hexanes/EtOAc 95:5 to 25:75). The partially purified material was then dissolved in methanol (25mL) and treated with potassium carbonate (0.17g, 1.2mmol). The reaction solution was stirred at room temperature for 18h, then it was concentrated in vacuo. The material obtained was purified by flash column chromatography (eluent: dichloromethane/methanol/concentrated ammonium hydroxide the title compound as a white foam (0.11g, 55% over two steps from 13).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3414 - 3422

57
[ 52605-52-4 ]
[ 6969-71-7 ]
[ 19794-93-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; In isopropyl alcohol; for 26h;Inert atmosphere; Reflux;	At room temperature to 2L three-necked flask, followed by adding 100g (0.323mol) N- (3- chloro - phenyl) -N '- (3- chloropropyl) - piperazine hydrochloride, 52.4g (0.388mol) of <strong>[6969-71-7]pyridine triadimefon</strong>, 1500mL isopropanol, mechanical agitation was added 29.7g (0.743mol) of sodium hydroxide, nitrogen, warmed to reflux, the reaction 26 hours, the HPLC detection N- (3- chloro - phenyl) -N ' - (3-chloropropyl) - piperazine and 0.02%.Controlling the temperature to 60 ~ 70 hot filtered and the filtrate was transferred to the reaction flask, supplemented 120mL10% aqueous sodium hydroxide solution was stirred heated under reflux for 8 hours, cooling to 5 crystallization, heat stirring for 2 hours, filtered, 50 vacuum dried was 110g (0.296mol) trazodone, yield 92%.
92%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 0.0222222h;Microwave irradiation;	Firstly, 276 mg (1 mmol) of 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride (5),135 mg (1 mmol) of 1,2,4-triazolo [4,3-a] pyridin-3-(2H)-one (1), 32 mg (0.1 mmol) of TBAB, 414 mg(3 mmol) of K2CO3, and 0.2 cm3 of acetonitrile were placed in a PTFE vessel, after which the mixturewas subjected to microwave radiation. The progress of the reaction was monitored by TLC (eluentchloroform-methanol 9:1). After the reaction, water was added and the resulting product was filteredo. After drying to solution 1-(3-chloropropyl)-4-(3-chloropheyl)piperazine (5) in acetone, a solutionof HCl in dioxane was added until acidic. The precipitated hydrochloride was filtered o on aBuechner funnel.

Reference： [1]Patent: CN105777745,2016,A .Location in patent: Paragraph 0042; 0043
[2]Molecules,2019,vol. 24

58
[ 109-04-6 ]
[ 6969-71-7 ]

Reference： [1]Patent: WO2017/46318,2017,A1
[2]Molecules,2019,vol. 24

59
[ 109-09-1 ]
[ 6969-71-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3855 - 3859
[2]Molecules,2019,vol. 24

60
[ 4930-98-7 ]
[ 6969-71-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3855 - 3859

61
N'-(pyridin-2-yl)formic hydrazide [ No CAS ]
[ 6969-71-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3855 - 3859

62
[ 6969-71-7 ]
2-[3-[4-(2,3-dichlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride [ No CAS ]

Reference： [1]Molecules,2019,vol. 24

63
[ 6969-71-7 ]
2-[3-[4-(2-fluorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride [ No CAS ]

Reference： [1]Molecules,2019,vol. 24

64
[ 6969-71-7 ]
2-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride [ No CAS ]

Reference： [1]Molecules,2019,vol. 24

65
[ 6969-71-7 ]
2-[3-[4-(2-ethoxyphenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride [ No CAS ]

Reference： [1]Molecules,2019,vol. 24

66
[ 6969-71-7 ]
[ 25332-39-2 ]

Reference： [1]Molecules,2019,vol. 24

67
[ 629-03-8 ]
[ 6969-71-7 ]
2-(6-bromohexyl)-1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 0.0166667h;Microwave irradiation;	Firstly, 1.35 g (10 mmol) of 1,2,4-triazolo [4,3-a] pyridin-3-(2H)-one (1), 4.6 cm3 (30 mmol) of1,6-dibromohexane, 0.322 g (1 mmol) of TBAB, 4.14 g (30 mmol) of K2CO3, and 2.5 cm3 of acetonitrile were placed in a conical flask, after which the mixture was subjected to microwave radiation for 60 s.The progress of the reaction was monitored by TLC (eluent chloroform-methanol 9:1). After the reaction, 15 cm3 of water was added to the mixture and extracted with methylene chloride. The product was purified by column chromatography (eluent chloroform-methanol 9:1).2-(3-bromohexyl)-1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one (8): 1H NMR (400 MHz, CDCl3) 7.78 (ddd,J = 5.5, 3.3, 2.2 Hz, 1H, ArH), 7.15-7.07 (m, 2H, ArH), 6.51 (ddd, J = 7.2, 4.4, 3.0 Hz, 1H, ArH), 4.02(t, J = 7.1 Hz, 2H, CHNCO), 3.42 (dd, J = 8.0, 5.6 Hz, 2H, CHBr), 1.89 (ddd, J = 10.3, 7.3, 3.4 Hz, 4H,CHAliph), 1.55-1.48 (m, 2H, CHAliph), 1.46-1.39 (m, 2H, CHAliph). 13C NMR (101 MHz, CDCl3) 148.57(Ar), 141.47 (Ar), 129.75 (Ar), 123.77 (Ar), 115.38 (Ar), 110.48 (Ar), 45.77 (CAliph), 33.69 (CAliph), 32.56(CAliph), 28.62 (CAliph), 27.71 (CAliph), 25.75 (CAliph). HPLC 91% (tR = 7.31), Rf = 0,96, yield = 79%, oil.

Reference： [1]Molecules,2019,vol. 24

68
[ 13078-15-4 ]
[ 109-70-6 ]
[ 6969-71-7 ]
[ 19794-93-5 ]

Yield	Reaction Conditions	Operation in experiment
71%		Firstly, 1.35 g (10 mmol) of 1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one (1), 2.5 cm3 (26 mmol) of1-bromo-3-chloropropane (2a), 322 mg (1 mmol) of TBAB, 8.28 g (60 mmol) of K2CO3, and 5 cm3 ofacetonitrile were placed in a conical flask. The reactions were carried out under microwave radiation(Samsung M182DN; 300 W) for 50 s. After this time, 2.3 g (10 mmol) of 1-(3-chlorophenyl)piperazine hydrochloride (4) and 5 cm3 of acetonitrile were added to the reaction mixture. Reactions were carriedout in the presence of microwave radiation for another 90 s. The progress of the reaction was monitoredby TLC (eluent chloroform-methanol 9:1). After the reaction, 50 cm3 of water was added and theresulting product was filtered o on a Buechner funnel. Yield (Samsung M182DN; 300 W) 31%, yield(CEM Discover SP reactor; 100 W) 71%.

Reference： [1]Molecules,2019,vol. 24

69
[ 52605-52-4 ]
[ 6969-71-7 ]
[ 25332-39-2 ]

Yield	Reaction Conditions	Operation in experiment
		Firstly, 2.76 g (10 mmol) of 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride (5),1.35 g (10 mmol) of 1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one (1), 322 mg (1 mmol) of TBAB, 4.14 g(30 mmol) of K2CO3, and a corresponding amount of acetonitrile (2, 6, or 8 cm3) were placed in aconical flask, after which the mixture was subjected to microwave radiation. The progress of thereaction was monitored by TLC (eluent chloroform-methanol 9:1). The reaction times are summarizedin Table 4. After the reaction, about 50 cm3 of water was added and the resulting product was filteredo on a Buechner funnel. The reaction yields are summarized in Table 4; Rf = 0.75.

Reference： [1]Molecules,2019,vol. 24

70
[ 109-04-6 ]
[ 563-41-7 ]
[ 6969-71-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In 2-ethoxy-ethanol; for 0.0333333h;Microwave irradiation;	Firstly, 350 mg (2.2 mmol) of 2-bromopyridine (6b), 491 mg (4.4 mmol) of semicarbazide hydrochloride, 0.75 cm3 of 2-ethoxyethanol, and 0.01 cm3 of concentrated sulfuric acid were placed ina PTFE vessel. Reactions were carried out under microwave radiation. The progress of the reaction was monitored by TLC (eluent chloroform-methanol 9:1). After 2 min, 0.75 cm3 of water was added tothe reaction mixture. The precipitate was filtered on a Buechner funnel and washed with about 5 cm3of water.

Reference： [1]Molecules,2019,vol. 24

71
[ 39577-43-0 ]
[ 6969-71-7 ]
[ 19794-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; acetonitrile; at 150℃;Flow reactor;Catalytic behavior;	General description of step 2 : Compound (II) and s-triazolo-[4,3-a]-pyridin-3-one (III) were continuously reacted in a flow reactor as schematically represented in Figure 2, to obtain trazodone base (IV). An alkaline aqueous solution of s-triazolo-[4,3-a]-pyridin-3-one (III) was used to feed channel 1 of a first fluidic module of the flow reactor (depicted as FM1 in Figure 2). An organic solution of Compound (II) was used to feed channel 2 of a second fluidic module of the flow reactor (depicted as FM2 in Figure 2). Both solutions were heated and the compounds were then allowed to react by continuously mixing the two solutions in a third fluidic module of the flow reactor (depicted as FM3 in Figure 2), at the same temperature. (0182) After collection, to determine the conversion into trazodone base (IV), the mixture was analysed by the FIPLC method described in Pharmacopoeia USP 40 NF 35 (December 1 , 2017), and the peak related to trazodone base (IV) evaluated against the peaks of a titration curve of a standard solution of pure trazodone base (IV).

Reference： [1]Patent: WO2019/154770,2019,A1 .Location in patent: Page/Page column 25-29

72
[ 6969-71-7 ]
2-(4-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)butyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]

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

73
[ 6940-78-9 ]
[ 6969-71-7 ]
2-(4-chlorobutyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Cooling with ice;	<strong>[6969-71-7][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one</strong>135mg, 1 mmol and potassium carbonate (152mg, 1.1 mmol)were added into DMF (5 mL), 1-bromo-4-chlorobutane (5mmol) was dripped under the ice bath, and the mixture was stirred at roomtemperature overnight. The reaction liquid was poured into ice water and extractedwith EA. The organic layer was washed with water and brine, dried overanhydrous sodium sulfate, concentrated under reduced pressure to obtain crudeproduct. The crude product is slurried in PE, filtered and dried to obtain a lightyellow solid (155 mg, 69%).

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

74
[ 6969-71-7 ]
6-isopropyl-2-oxo-9-(2-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)ethoxy)-10-(thiazol-2-yl)-6,7-dihydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: CN110903284,2020,A

75
[ 106-93-4 ]
[ 6969-71-7 ]
2-(2-bromoethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.7%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 6h;	At room temperature, [1,2,4] triazolo [4,3-a] pyridine-3 (2H) -one (500mg, 3.70mmol), 1,2-bromomethane (0.73mL, 8.50mmol) and DMF (10.0 mL), then NaH (125 mg) was added, and the reaction mixture was stirred at room temperature for 6 h.The reaction was quenched by adding water (30 mL), and then extracted with EA (30 mL × 2). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to remove the solvent. Petroleum ether (10 mL) was added to it, stirred for 30 min, filtered, the filtrate was collected, and dried in vacuo to give the title compound as a red solid (490 mg, 2.02 mmol, 54.70%).

Reference： [1]Patent: CN110903284,2020,A .Location in patent: Paragraph 0691; 0693-0696

76
[ 629-03-8 ]
[ 6969-71-7 ]
2-(6-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)hexyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry,2020

77
[ 39149-80-9 ]
[ 6969-71-7 ]
tert-butyl 2-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In acetonitrile; at 60℃; for 20h;	To a stirred suspension of [1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (0.15 g, 1.1 mmol) in MeCN (4.5 mL) was added tert-butyl 2-bromopropanoate (184.2 muL, 1.11 mmol) and K2CO3 (0.46 g, 3.33 mmol). The reaction was stirred at 60 oC for 20 h. The reaction was allowed to cool to room temperature and filtered, rinsing with MeCN. The filtrate was concentrated. The crude product was purified by Biotage Isolera chromatography (silica gel, eluting with 0-36% EtOAc in heptane) to give 173 mg (58% yield) the title compound as a white solid.1H NMR (500 MHz, Chloroform-d) d 7.75 (dt, J = 7.1, 1.2 Hz, 1H), 7.12 (dt, J = 9.5, 1.1 Hz, 1H), 7.07 (ddd, J = 9.5, 6.2, 1.2 Hz, 1H), 6.47 (td, J = 6.8, 6.3, 1.1 Hz, 1H), 1.75 (d, J = 7.4 Hz, 3H), 1.45 (s, 10H). LCMS (Analytical Method D) Rt = 0.99 min, MS (ESIpos): m/z= 208.30 [M-tBu+H]+. (0999) [98%].

Reference： [1]Patent: WO2020/97609,2020,A1 .Location in patent: Page/Page column 221

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[ 6969-71-7 ] Synthesis Path-Upstream 1~9

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