[ CAS No. 60719-84-8 ] {[proInfo.proName]}

Name: 60719-84-8|5-Amino-[3,4'-bipyridin]-6(1H)-one|99%
Brand: Ambeed
SKU: A110103
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Quality Control of [ 60719-84-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 60719-84-8 ]

SDS Specification

Alternatived Products of [ 60719-84-8 ]

Product Details of [ 60719-84-8 ]

CAS No. :	60719-84-8	MDL No. :	MFCD00083228
Formula :	C₁₀H₉N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RNLQIBCLLYYYFJ-UHFFFAOYSA-N
M.W :	187.20	Pubchem ID :	3698
Synonyms :	Inamrinone;WIN 40,680	Chemical Name :	5-Amino-[3,4'-bipyridin]-6(1H)-one

Calculated chemistry of [ 60719-84-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	54.7
TPSA :	71.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.14
Log Po/w (XLOGP3) :	-0.16
Log Po/w (WLOGP) :	1.03
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	1.88
Consensus Log Po/w :	0.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.47
Solubility :	6.37 mg/ml ; 0.034 mol/l
Class :	Very soluble
Log S (Ali) :	-0.89
Solubility :	24.0 mg/ml ; 0.128 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.0358 mg/ml ; 0.000191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 60719-84-8 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 60719-84-8 ]

* 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 [ 60719-84-8 ]
Downstream synthetic route of [ 60719-84-8 ]

[ 60719-84-8 ] Synthesis Path-Upstream 1~10

1
[ 62749-46-6 ]
[ 60719-84-8 ]

Reference： [1] Pharmazie, 1986, vol. 41, # 3, p. 173 - 175
[2] Patent: US4072746, 1978, A,
[3] Patent: US4107315, 1978, A,
[4] Patent: US4004012, 1977, A,

2
[ 934200-37-0 ]
[ 60719-84-8 ]

Reference： [1] Heterocycles, 2006, vol. 70, p. 509 - 517

3
[ 62749-33-1 ]
[ 60719-84-8 ]

Reference： [1] Patent: US4107315, 1978, A,
[2] Patent: US4004012, 1977, A,

4
[ 62749-33-1 ]
[ 60719-84-8 ]

Reference： [1] Patent: US4072746, 1978, A,

5
[ 893440-43-2 ]
[ 60719-84-8 ]

Reference： [1] Heterocycles, 2006, vol. 70, p. 509 - 517

6
[ 893440-45-4 ]
[ 60719-84-8 ]

Reference： [1] Heterocycles, 2006, vol. 70, p. 509 - 517

7
[ 147269-68-9 ]
[ 60719-84-8 ]

Reference： [1] Heterocycles, 2006, vol. 70, p. 509 - 517

8
[ 62749-26-2 ]
[ 60719-84-8 ]

Reference： [1] Pharmazie, 1986, vol. 41, # 3, p. 173 - 175
[2] Patent: US4004012, 1977, A,

9
[ 26866-49-9 ]
[ 60719-84-8 ]

Reference： [1] Patent: US4004012, 1977, A,
[2] Patent: US4004012, 1977, A,

10
[ 51076-46-1 ]
[ 60719-84-8 ]

Reference： [1] Patent: US4004012, 1977, A,

[ 60719-84-8 ] Synthesis Path-Downstream 1~87

1
[ 50-00-0 ]
[ 60719-84-8 ]
[ 69438-66-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1987,vol. 329,p. 793 - 803

2
[ 62749-46-6 ]
[ 60719-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine; In water;	F-1. 3-Amino-5-(4-pyridinyl)-2(1H)-pyridinone --To a solution containing 90 g. of sodium hydroxide in 1300 ml. of water kept at 0° C. was added dropwise with stirring 23 ml. of bromine. To the reaction mixture was then added 80 g. of 1,2-dihydro-2-oxo-5-(4-pyridinyl)nicotinamide and the resulting reaction mixture was heated on a steam bath for three hours. The reaction mixture was cooled to room temperature, acidified slowly with 6N hydrochloric acid and the resulting acidic mixture was stirred for an additional thirty minutes. The acidic mixture was neutralized with 10percent aqueous potassium bicarbonate solution and the mixture cooled. The precipitate was collected, washed with water and dried. The solid product was recrystallized from dimethylformamide, washed successively with methanol and ethyl ether and dried in vacuo at 80° C. to yield 35 g. of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 295°-297° C. with decomposition. Another 7 g. of the product was obtained by diluting the mother liquor with ethyl ether.
	With sodium hydroxide; bromine; In water;	F-1. 3-Amino-5-(4-pyridinyl)-2(1H)-pyridinone -- To a solution containing 90 g. of sodium hydroxide in 1300 ml. of water kept at 0° C. was added dropwise with stirring 23 ml. of bromine. To the reaction mixture was then added 80 g. of 1,2-dihydro-2-oxo-5-(4-pyridinyl)nicotinamide and the resulting reaction mixture was heated on a steam bath for three hours. The reaction mixture was cooled to room temperature, acidified slowly with 6N hydrochloric acid and the resulting acidic mixture was stirred for an additional thirty minutes. The acidic mixture was neutralized with 10percent aqueous potassium bicarbonate solution and the mixture cooled. The precipitate was collected, washed with water and dried. The solid product was recrystallized from dimethylformamide, washed successively with methanol and ethyl ether and dried in vacuo at 80° C. to yield 35 g. of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 295°-297° C. with decomposition. Another 7 g. of the product was obtained by diluting the mother liquor with ethyl ether.
	With sodium hydroxide; bromine; In water;	F-1. 3-Amino-5-(4-pyridinyl)-2(1H)-pyridinone --To a solution containing 90 g. of sodium hydroxide in 1300 ml. of water kept at 0° C. was added dropwise with stirring 23 ml. of bromine. To the reaction mixture was then added 80 g. of 1,2-dihydro-2-oxo-5-(4-pyridinyl)nicotinamide and the resulting reaction mixture was heated on a steam bath for 3 hours. The reaction mixture was cooled to room temperature, acidified slowly with 6N hydrochloric acid and the resulting acidic mixture was stirred for an additional 30 minutes. The acidic mixture was neutralized with 10percent aqueous potassium bicarbonate solution and the mixture cooled. The precipitate was collected, washed with water and dried. The solid product was recrystallized from dimethylformamide, washed successively with methanol and ethyl ether and dried in vacuo at 80° C. to yield 35 g. of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 295°-297° C. with decomposition. Another 7 g. of the product was obtained by diluting the mother liquor with ethyl ether.

Reference： [1]Pharmazie,1986,vol. 41,p. 173 - 175
[2]Patent: US4072746,1978,A
[3]Patent: US4107315,1978,A
[4]Patent: US4004012,1977,A

4
[ 934200-37-0 ]
[ 60719-84-8 ]

Reference： [1]Heterocycles,2006,vol. 70,p. 509 - 517

5
[ 893440-43-2 ]
[ 60719-84-8 ]

Reference： [1]Heterocycles,2006,vol. 70,p. 509 - 517

6
[ 893440-45-4 ]
[ 60719-84-8 ]

Reference： [1]Heterocycles,2006,vol. 70,p. 509 - 517

7
[ 147269-68-9 ]
[ 60719-84-8 ]

Reference： [1]Heterocycles,2006,vol. 70,p. 509 - 517

8
[ 62749-26-2 ]
[ 60719-84-8 ]

Reference： [1]Pharmazie,1986,vol. 41,p. 173 - 175
[2]Patent: US4004012,1977,A

9
[ 98-09-9 ]
[ 60719-84-8 ]
N-(2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In pyridine; for 2.0h;	<strong>[60719-84-8]Amrinone</strong> (100 mg, 0.53 mmol) was suspended in pyridine (2 mL) and benzenesulfonyl chloride (75 muL, 0.59 mmol) was added dropwise at 0°C. The reaction mixture was stirred for 2 hours. The pyridine was removed in vacuo. MeOH was added to the crude mixture and the solid was filtered and rinsed with more MeOH to give the title compound as a light yellow solid (100 mg, 57percent yield). MS (ES+) m/e = 328. 1H NMR (DMSO-d6) 5H 7.51 (2H, dd), 7.54-7.58 (2H, m), 7.61-7.65 (IH, m), 7.75 (2H, dd), 7.90 (2H, dd), 8.56 (2H, dd), 9.78 (IH, br s), 12.33 (IH, br s).
21%	With pyridine; at 20.0℃; for 16.0h;Inert atmosphere;	General procedure: Benzoyl chloride (0.062mL, 0.53mmol, 1 equivalent) was added dropwise to 3-amino-5-(pyridin-4-yl)pyridin-2-one (100mg, 0.53mmol, 1 equivalent) in pyridine (3 mL) and the mixture was stirred for 16h at room temperature. The solvent was removed under reduced pressure and the residue taken up in methanol and filtered to give the desired product as a light-yellow solid (41mg, 27percent).

Reference： [1]Patent: WO2006/65946,2006,A1 .Location in patent: Page/Page column 100
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3021 - 3029

10
[ 60719-84-8 ]
[ 1710-98-1 ]
3-(4-tert-butylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	In pyridine; at 20.0℃;	<strong>[60719-84-8]Amrinone</strong> (200 mg, 1.07 mmol) was suspended in pyridine (5 mL) and 4-tert- butylbenzoyl chloride (209 muL, 1.07 mmol) was added. The reaction mixture was stirred overnight at room temperature. The solid was filtered and rinsed with MeOH to give the title compound as a pink solid (33 mg, 9percent yield). MS (ES+) m/e = 348. 1H NMR (DMSO-d6) 6H 1.43 (9H, s), 7.57-7.62 (4H, m), 7.81 (IH, s), 7.88 (2H, d), 8.59 (2H, d), 8.78 (IH, d), 9.32 (IH, s), 12.61 (IH, s).

Reference： [1]Patent: WO2006/65946,2006,A1 .Location in patent: Page/Page column 62

11
[ 7440-44-0 ]
[ 60719-84-8 ]
[ 13831-31-7 ]
3-(acetoxyacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; acetic acid; acetone;	EXAMPLE 5 3-(Acetoxyacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone To a stirred mixture containing 9.35 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> and 100 ml. of dried pyridine under an atmosphere of nitrogen (bubbled slowly through the reaction mixture) was added dropwise with stirring over a period of about 8 minutes 8.22 g. of acetoxyacetyl chloride whereupon the reaction temperature rose from 22° to 44° C. The reaction mixture was stirred for 2 and 1/2 hours and was allowed to stand at room temperature overnight under nitrogen. To the reaction mixture was added acetone (200 ml.) and the mixture stirred well. The separated solid was collected, washed with acetone, air-dried, and then dried in vacuo at 80° C. to yield 16.3 g. of the crude product as its hydrochloride salt. A 6.5 g. portion of product was dissolved in hot acetic acid to which was added a small amount of hydrogen chloride in ethanol (aided dissolution). The hot solution was treated with decolorizing charcoal, filtered to give a bright yellow filtrate from which crystals separated. The mixture was allowed to cool to room temperature and stand overnight. The crystalline precipitate was collected, washed with acetone and dried in vacuo at 90° C. for about 40 hours to yield 5.2 g. of 3-(acetoxyacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone as its monohydrochloride hemiacetate, m.p. 267°-290° C. with decomposition.

Reference： [1]Patent: US4271168,1981,A

12
[ 123-54-6 ]
[ 60719-84-8 ]
3-[(1-methyl-3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	EXAMPLE 1 3-[(1-Methyl-3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone A mixture containing 41 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 170 ml. of n-pentane-2,4-dione and 850 ml. of dimethylformamide was heated with stirring on a steam bath for seven hours and allowed to cool to room temperature. The crystalline product that separated was collected by filtration, washed successively with ethanol and acetone and dried to yield 29.2 g. of 3-[(1-methyl-3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 282°-284° C. Acid-addition salts of 3-[(1-methyl-3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone are conveniently prepared by carefully adding to a mixture of 1 g. of 3-[(1-methyl-3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone in about 20 ml. of aqueous methanol the appropriate acid, e.g., methanesulfonic acid, concentrated sulfuric acid, concentrated phosphoric acid, to a pH of about 2 to 3, chilling the mixture after partially evaporating and collecting the precipitated salt, e.g., dimethanesulfonate, sulfate, phosphate, respectively.

Reference： [1]Patent: US4362735,1982,A

13
[ 60719-84-8 ]
3-(acetoacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	EXAMPLE 2 3-(Acetoacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone, alternatively named N-(1,6-dihydro-6-oxo-[3,4'-bipyridin]-5-yl)-3-oxobutanamide To a stirred suspension containing 9.4 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> suspended in 250 ml. of tetrahydrofuran chilled in an ice bath was added dropwise over a period of 5 minutes 6.3 g. of diketene and the resulting mixture was stirred for an additional 10 minutes while cold. The ice bath was replaced with a steam bath and the reaction mixture was refluxed gently with stirring for 1 hour. The reaction mixture was then cooled and the separated solid was collected, washed well with ether and air-dried to give 12.1 g. of 3-(acetoacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 208°-210° C. with the composition. Acid-addition salts of 3-(acetoacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone are conveniently prepared by adding to a mixture of 0.5 g. of 3-acetoacetylamino)-5-(4-pyridinyl)-2(1H)-pyridinone in about 10 ml. of aqueous methanol the appropriate acid, e.g., methanesulfonic acid, concentrated sulfuric acid, concentrated phosphoric acid, to a pH of about 2 to 3, chilling the mixture after partial evaporation and collecting the precipitated salt, e.g., dimethanesulfonate, sulphate, phosphate, respectively.

Reference： [1]Patent: US4271168,1981,A

14
[ 51731-17-0 ]
[ 60719-84-8 ]
3-[(3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	EXAMPLE 2 3-[(3-Oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone A mixture containing 24 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 50 ml. of 4-methoxy-3-buten-2-one and 450 ml. of dimethylformamide was heated on a steam bath for twelve hours and then allowed to cool to room temperature. After chilling in an ice bath, the crystalline product was collected by filtration, washed successively with dimethylformamide and ethyl acetate, and then dried to yield 26 g. of 3-[(3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone, m.p.>300° C. Acid-addition salts of 3-[(3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2(1H)-pyridinone are conveniently prepared by carefully adding to a mixture of 1 g. of 3-[(3-oxo-1-butenyl)amino]-5-(4-pyridinyl)-2-(1H)-pyridinone in about 20 ml. of aqueous methanol the appropriate acid, e.g., methanesulfonic acid, concentrated sulfuric acid, concentrated phosphoric acid, to a pH of about 2 to 3, chilling the mixture after partially evaporating and collecting the precipitated salt, e.g., dimethanesulfonate, sulfate, phosphate, respectively.

Reference： [1]Patent: US4362735,1982,A

15
N-hydroxy-1,2-dihydro-2-oxo-5-(4-pyridinyl)nicotinimidamide [ No CAS ]
[ 60719-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; PPA; In water;	D-1. 3-Amino-5-(4-pyridinyl)-2(1H)pyridinone A mixture containing 2.0 g. of N-hydroxy-1,2-dihydro-2-oxo-5-(4-pyridinyl)nicotinimidamide and 16 g. of polyphosphoric acid was stirred with a glass rod until a stiff paste was obtained. The mixture was then heated on a steam bath with occasional stirring for 12 hours and then allowed to stand at room temperature over the weekend. The reaction mixture was warmed a little to soften the viscous mixture which was then treated with about 100 ml. of water and mixed well to dissolve the excess polyphosphoric acid. A yellow solid material that separated was collected, suspended in fresh water and to the suspension was added ammonium hydroxide until the mixture was distinctly alkaline. The solid which did not dissolve was collected, washed with a little water and dried in a vacuum oven at 90° C. to produce 0.9 g. of 3-amino-5-(4-pyridinyl)-2(1H)pyridinone, m.p. 293°-295° C. with decomposition. This product was identical with a sample of amrinone, that is, 3-amino-5-(4-pyridinyl)-2(1H)pyridinone which had been prepared from its corresponding 3-carbamyl precursor as shown in U.S. Pat. No. 4,072,746.

Reference： [1]Patent: US4305948,1981,A

16
[ 60719-84-8 ]
[ 62749-47-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; acetic anhydride;	G-1. N-[1,2-Dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]acetamide -- A mixture containing 9.4 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 5,6 g. of acetic anhydride and 120 ml. of pyridine was heated on a steam bath for one hour and then allowed to cool. The separated product was collected, washed with ether and dried, and recrystallized twice from dimethylformamide to yield 8 g. of N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]acetamide, m.p. >300° C.
	With pyridine; acetic anhydride;	G-1. N-[1,2-Dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]acetamide -- A mixture containing 9.4 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 5.6 g. of acetic anhydride and 120 ml. of pyridine was heated on a steam bath for one hour and then allowed to cool. The separated product was collected, washed with ether and dried, and recrystallized twice from dimethylformamide to yield 8 g. of N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]acetamide, m.p. >300° C.
	With pyridine; acetic anhydride;	G-1. N-[1,2-Dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]acetamide -- A mixture containing 9.4 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 5.6 g. of acetic anhydride and 120 ml. of pyridine was heated on a steam bath for 1 hour and then allowed to cool. The separated product was collected, washed with ether and dried, and recrystallized twice from dimethylformamide to yield 8 g. of N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]acetamide, m.p. >300° C.

Reference： [1]Patent: US4072746,1978,A
[2]Patent: US4107315,1978,A
[3]Patent: US4004012,1977,A

17
[ 60719-84-8 ]
N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]-imidazole-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		G-7. n-Hexyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]carbamate using <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> and then reacting the resulting N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]-imidazole-1-carboxamide with n-hexanol.
		G-7. n-Hexyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]carbamate using <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> and then reacting the resulting N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]-imidazole-1-carboxamide with n-hexanol.

Reference： [1]Patent: US4107315,1978,A
[2]Patent: US4004012,1977,A

18
[ 89845-65-8 ]
[ 60719-84-8 ]
3-amino-5-(4-pyridinyl)-2(1H)-pyridinone sulfate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanesulfonic acid; sulfuric acid; In methanol;	-- A 20 g. portion of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> was suspended in 250 ml. of warm methanol and methanesulfonic acid was added in a fine stream until the pH of the mixture dropped to about 2 to 3. The mixture was chilled and the separated orange solid was collected. The crystalline solid was recrystallized twice from aqueous methanol to yield, as golden crystals, 14 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> methanesulfonate, m.p. 280°-282° C. with decomposition, after drying in vacuo at 80° C. Sulfate -- To a solution containing 10 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> in about 250 ml. of aqueous methanol was added carefully concentrated sulfuric acid until the pH of the solution became 3. A yellow solid formed and the mixture was chilled. The separated solid was collected, recrystallized from water and dried at 80° C. and 0.11 mm. to yield 16.0 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> sulfate, m.p. 287°-288° C. with decomposition.
	With methanesulfonic acid; sulfuric acid; In methanol;	The preparations of several acid-addition salts of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> are given in the following paragraphs. Methanesulfonate -- A 20 g. portion of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> was suspended in 250 ml. of warm methanol and methanesulfonic acid was added in a fine stream until the pH of the mixture dropped to about 2 to 3. The mixture was chilled and the separated orange solid was collected. The crystalline solid was recrystallized twice from aqueous methanol to yield, as golden crystals, 14 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> methanesulfonate, m.p. 280°-282° C. with decomposition, after drying in vacuo at 80° C. Sulfate -- To a solution containing 10 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> in about 250 ml. of aqueous methanol was added carefully concentrated sulfuric acid until the pH of the solution became 3. A yellow solid formed and the mixture was chilled. The separated solid was collected, recrystallized from water and dried at 80° C. and 0.11 mm. to yield 16.0 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> sulfate, m.p. 287°-288° C. with decomposition.
	With methanesulfonic acid; sulfuric acid; In methanol;	The preparations of several acid-addition salts of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> are given in the following paragraphs. Methanesulfonate -- A 20 g. portion of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> was suspended in 250 ml. of warm methanol and methanesulfonic acid was added in a fine stream until the pH of the mixture dropped to about 2 to 3. The mixture was chilled and the separated orange solid was collected. The crystalline solid was recrystallized twice from aqueous methanol to yield, as golden crystals, 14 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> methanesulfonate, m.p. 280°-282° C. with decomposition, after drying in vacuo at 80° C. Sulfate -- To a solution containing 10 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> in about 250 ml. of aqueous methanol was added carefully concentrated sulfuric acid until the pH of the solution became 3. A yellow solid formed and the mixture was chilled. The separated solid was collected, recrystallized from water and dried at 80° C. and 0.11 mm. to yield 16.0 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> sulfate, m.p. 287°-288° C. with decomposition.

Reference： [1]Patent: US4072746,1978,A
[2]Patent: US4107315,1978,A
[3]Patent: US4004012,1977,A

19
[ 62749-33-1 ]
[ 60719-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	palladium; In N-methyl-acetamide;	D-1. 3-Amino-5-(4-pyridinyl)-2(1H)-pyridinone -- A mixture containing 10 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 200 ml. of dimethylformamide and 1.5 g. of 10percent palladium-on-charcoal was hydrogenated under pressure (50 p.s.i.) at room temperature until the uptake of hydrogen ceased (about thiry minutes). The reaction mixture was filtered through infusorial earth and the filtrate was heated in vacuo to remove the solvent. The residual material was crystallized from dimethylformamide, washed successively with ethanol and ether, and dried in a vacuum oven at 80° C. for 8 hours to yield 6 g. of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 294°-297° C. with decomposition.
	palladium; In N-methyl-acetamide;	D-1. 3-Amino-5-(4-pyridinyl)-2(1H)-pyridinone -- A mixture containing 10 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 200 ml. of dimethylformamide and 1.5 g. of 10percent palladium-on-charcoal was hydrogenated under pressure (50 p.s.i.) at room temperature until the uptake of hydrogen ceased (about 30 minutes). The reaction mixture was filtered through infusorial earth and the filtrate was heated in vacuo to remove the solvent. The residual material was crystallized from dimethylformamide, washed successively with ethanol and ether, and dried in a vacuum oven at 80° C. for 8 hours to yield 6 g. of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 294°-297° C. with decomposition.

Reference： [1]Patent: US4107315,1978,A
[2]Patent: US4004012,1977,A

20
[ 7440-44-0 ]
[ 87-13-8 ]
[ 60719-84-8 ]
diethyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]aminomethylenemalonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; ethanol;	J-1. Diethyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]aminomethylenemalonate (also named diethyl [1,6-dihydro-6-oxo-(3,4'-bipyridin)-5-ylaminomethylene]propanedioate) -- A mixture containing 9.4 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 10.8 g of diethyl ethoxymethylenemalonate and 100 ml. of ethanol was refluxed with stirring on a steam bath for six and one-half hours. The reaction mixture was filtered through infusorial earth and the filtrate was distilled in vacuo to remove the solvent. The solid residue was recrystallized once from ethanol and then once from methanol using decolorizing charcoal, washed successively with isopropyl alcohol and ether, and then dried to yield 22 g. of diethyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]aminomethylenemalonate, m.p. 218°-222° C.
	In methanol; ethanol;	J-1. Diethyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]aminomethylenemalonate (also named diethyl [1,6-dihydro-6-oxo-(3,4'-bipyridin)-5-ylaminomethylene]propanedioate) - A mixture containing 9.4 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 10.8 g. of diethyl ethoxymethylenemalonate and 100 ml. of ethanol was refluxed with stirring on a steam bath for 61/2 hours. The reaction mixture was filtered through infusorial earth and the filtrate was distilled in vacuo to remove the solvent. The solid residue was recrystallized once from ethanol and then once from methanol using decolorizing charcoal, washed successively with isopropyl alcohol and ether, and then dried to yield 22 g. of diethyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]aminomethylenemalonate, m.p. 218°-222° C.

Reference： [1]Patent: US4072746,1978,A
[2]Patent: US4107315,1978,A

21
[ 7440-44-0 ]
[ 60719-84-8 ]
[ 69438-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; formic acid;	I-2. 3-Dimethylamino-5-(4-pyridinyl)-2(1H)-pyridinone (also named 5-(dimethylamino)-[3,4-bipyridin]-6-(1H)-one) - A mixture contaning 36 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong>, 40 g. of 30percent aqueous formaldehyde solution and 400 ml. of formic acid was refluxed for 21/2 hours and cooled. The reaction mixture was heated in vacuo to remove the excess formaldehyde and formic acid and the remaining material was neutralized with 10percent potassium bicarbonate solution and allowed to stand at room temperature over the weekend. The aqueous mixture was extracted with three 150 ml. portions of methylene dichloride and the combined extracts were dried over anhydrous magnesium sulfate and treated with decolorizing charcoal, filtered and the filtrate heated in vacuo to remove the methylene dichloride. The residue was recrystallized twice from acetonitrile, washed with ether and dried in a vacuum oven at 80° C. to yield 11.5 g. of 3-dimethylamino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 190°- 194° C.

Reference： [1]Patent: US4107315,1978,A

22
[ 60719-84-8 ]
N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]formamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; In water;	G-9. N-[1,2-Dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]formamide (also named N-(1,6-dihydro-6-oxo[3,4'-bipyridine]-5yl)formamide) -- A reaction mixture containing 28 g. of 3-amino-5-(4-pyridinyl)-2-(1H)-pyridinone and 200 ml. of 97percent formic acid was heated on a steam bath for three hours, cooled and the excess formic acid distilled-off under reduced pressure. The residue was dissolved in water and the aqueous solution was made alkaline with ammonium hydroxide. The precipitated product was collected, washed with water, dried, recrystallized from dimethylformamide, washed with ether and dried to yield 26 g. of N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]formamide, m.p. 299°-300° C. with decomposition.
	With formic acid; In water;	G-9. N-[1,2-Dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]formamide (also named N-(1,6-dihydro-6-oxo-[3,4'-bipyridine]-5-yl)formamide) -- A reaction mixture containing 28 g. of <strong>[60719-84-8]3-amino-5-(4-pyridinyl)-2(1H)-pyridinone</strong> and 200 ml. of 97percent formic acid was heated on a steam bath for 3 hours, cooled and the excess formic acid distilled-off under reduced pressure. The residue was dissolved in water and the aqueous solution was made alkaline with ammonium hydroxide. The precipitated product was collected, washed with water, dried, recrystallized from dimethylformamide, washed with ether and dried to yield 26 g. of N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]formamide, m.p. 299°-300° C. with decomposition.

Reference： [1]Patent: US4072746,1978,A
[2]Patent: US4107315,1978,A

23
[ 62749-33-1 ]
methansulfonate [ No CAS ]
[ 60719-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	palladium; In N-methyl-acetamide;	D-1. 3-Amino-5-(4-pyridinyl)-2(1H)-pyridinone -- A mixture containing 10 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 200 ml. of dimethylformamide and 1.5 g. of 10percent palladium-on-charcoal was hydrogenated under pressure (50 p.s.i.) at room temperature until the uptake of hydrogen ceased (about thirty minutes). The reaction mixture was filtered through infursorial earth and the filtrate was heated in vacuo to remove the solvent. The residual material was crystallized from dimethylformamide, washed successively with ethanol and ether, and dried in a vacuum oven at 80° C. for eight hours to yield 6 g. of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 294°-297° C. with decomposition. The preparations of several acid-addition salts of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone are given in the following paragraphs. Methansulfonate

Reference： [1]Patent: US4072746,1978,A

24
[ 60719-84-8 ]
1-(3-bromopropyl)-4-(p-tolyl)piperazine [ No CAS ]
[ 1192490-97-3 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7397 - 7409

25
[ 60719-84-8 ]
(2S)-2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid [ No CAS ]
[ 1240522-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 168.0h;	(S)-tert-butyl 3-(3-chlorophenyl)-l-oxo-l-(2-oxo-5-(pyridin-4-yl)-l,2- dihydropyridin-3-ylamino)propan-2-ylcarbamate (25.1. C). <strong>[60719-84-8]Amrinone</strong> 25.1.A (Sigma, 250 mg, 1.33 mmol), (S)-2-(tert-butoxycarbonyl)-3-(3-chlorophenyl)propanoic acid 25.1.B (400 mg, 1.33 mmol), HBTU (608 mg, 1.60 mmol), and DIPEA (350 muL, 2.00 mmol) were stirred in DMF (10 ml) at room temperature for a week. The reaction mixture was diluted with water and filtered and the resulting solid was used in the next step without further purification.

Reference： [1]Patent: WO2010/93849,2010,A2 .Location in patent: Page/Page column 98

26
[ 182570-26-9 ]
[ 60719-84-8 ]
[ 1213262-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	To a solution of 6-1 (1 equiv), DIEA (5 equiv), and 6-methoxy-3- carboxylic acid (1.1 equiv) in DMF was added HATU (1.1 equiv). After stirring the solution at room temperature overnight (LC-MS showed complete reaction), the solvents were removed in vacuum. The residue was suspended in ethyl acetate, and washed by brine (2x), saturated sodium bicarbanate (3x), and brine (3x), dried over sodium sulfate, and evaporated in vacuum to give crude amide 6-2. This crude intermediate was used directly in the next step without further purification. Thus, Lawesson's reagent (0.5 equiv) was added to a suspension of crude 6-2 in toluene. The suspension was heated at 95 C overnight. The solvents were removed in vacuum, and the residue was subjected to preparative HPLC to give the final product 6-3 (Example 149).

Reference： [1]Patent: WO2010/24903,2010,A1 .Location in patent: Page/Page column 95-96

27
[ 103-82-2 ]
[ 60719-84-8 ]
3-phenylacetamido-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

28
[ 22090-27-3 ]
[ 60719-84-8 ]
3-(4-(pyrrolidin-1-yl)benzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

29
[ 22090-24-0 ]
[ 60719-84-8 ]
N-(2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridin-3-yl)-4-piperidin-1-ylbenzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

30
[ 619-65-8 ]
[ 60719-84-8 ]
3-(4-cyanobenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

31
[ 2438-05-3 ]
[ 60719-84-8 ]
3-(4-propylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

32
[ 20029-52-1 ]
[ 60719-84-8 ]
3-(4-cyclohexylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

33
[ 619-64-7 ]
[ 60719-84-8 ]
3-(4-ethylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

34
[ 619-84-1 ]
[ 60719-84-8 ]
3-(4-dimethylaminobenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

35
[ 99-94-5 ]
[ 60719-84-8 ]
3-(4-methylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

36
[ 98-73-7 ]
[ 60719-84-8 ]
3-(4-tert-butylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

37
[ 65-85-0 ]
[ 60719-84-8 ]
N-(2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridin-3-yl)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

38
[ 60719-84-8 ]
[ 99-04-7 ]
3-(3-methylbenzoylamino)-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2341 - 2350

39
[ 60719-84-8 ]
[ 98-89-5 ]
3-cyclohexanoylamino-5-(pyridin-4-yl)-(1H)-pyridin-2-one [ No CAS ]