[ CAS No. 38767-72-5 ] {[proInfo.proName]}

Name: 38767-72-5|4-Aminopyridin-2(1H)-one|97%
Brand: Ambeed
SKU: A265577
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Quality Control of [ 38767-72-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 38767-72-5 ]

SDS Specification

Alternatived Products of [ 38767-72-5 ]

Product Details of [ 38767-72-5 ]

CAS No. :	38767-72-5	MDL No. :	MFCD09832889
Formula :	C₅H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SBQVQYPJWLJRQT-UHFFFAOYSA-N
M.W :	110.11	Pubchem ID :	573530
Synonyms :

Calculated chemistry of [ 38767-72-5 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	31.47
TPSA :	58.88 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) :	-7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.76
Log Po/w (XLOGP3) :	-0.76
Log Po/w (WLOGP) :	-0.03
Log Po/w (MLOGP) :	-0.4
Log Po/w (SILICOS-IT) :	0.87
Consensus Log Po/w :	0.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.6
Solubility :	27.7 mg/ml ; 0.252 mol/l
Class :	Very soluble
Log S (Ali) :	0.0
Solubility :	110.0 mg/ml ; 1.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	3.4 mg/ml ; 0.0309 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 38767-72-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 38767-72-5 ]

* 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 [ 38767-72-5 ]
Downstream synthetic route of [ 38767-72-5 ]

[ 38767-72-5 ] Synthesis Path-Upstream 1~7

1
[ 14432-12-3 ]
[ 38767-72-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydroxide In toluene at 170℃; for 72 h; Sealed tube	A mixture of 2-chloro-4-aminopyridine 3 (127 mg, 1.0 mmol) and KOH (280.6mg, 5.0 mmol) in toluene (4.0 mL) was heated at 170°C in a sealed tube for 72h. Themixture was cooled to r.t. and the toluene was removed. The residue was purified byflash chromatography on silica gel (DCM/MeOH/NH4OH: 78/20/2) to give 5 (107 mg,97percent) as a pale yellow solid

Reference： [1] Synlett, 2016, vol. 27, # 1, p. 67 - 69
[2] Tetrahedron, 1999, vol. 55, # 41, p. 11985 - 11996

2
[ 95306-61-9 ]
[ 38767-72-5 ]

Reference： [1] Synthesis, 1984, # 9, p. 765 - 766

3
[ 626-03-9 ]
[ 38767-72-5 ]

Reference： [1] Synthesis, 1984, # 9, p. 765 - 766

4
[ 109-09-1 ]
[ 38767-72-5 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 41, p. 11985 - 11996

5
[ 2402-95-1 ]
[ 38767-72-5 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 41, p. 11985 - 11996

6
[ 14432-16-7 ]
[ 38767-72-5 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 41, p. 11985 - 11996

7
[ 38767-72-5 ]
[ 96530-75-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	at -20 - 60℃; for 3.5 h;	To a cooled solution of HF-pyridine complex (70percent, 13.1 mL) at 0°C was slowlyadded 4-amino-2-pyridone 5 (1.85 g, 16.8 mmol). The mixture was cooled to -20°Cand tBuONO (3.0 mL, 25.2 mmol) was slowly added. The reaction mixture wasstirred at -20°C for 0.5h, then allowed to warm to r.t. for 2h and finally heated at 60°Cfor 1h. The mixture was cooled to 0°C and sat. aq. Na2CO3 was added. The aqueouslayer was extracted with ethyl acetate (5x), and the combined organic layers weredried (Na2SO4), filtered and concentrated under reduced pressure. The crude waspurified by flash chromatography on silica gel (DCM/MeOH: 95/5) to give 1a (1.14 g,60percent) as a colorless solid.

Reference： [1] Synlett, 2016, vol. 27, # 1, p. 67 - 69

[ 38767-72-5 ] Synthesis Path-Downstream 1~67

1
[ 95306-61-9 ]
[ 38767-72-5 ]

Reference： [1]Synthesis,1984,p. 765 - 766

2
[ 89291-77-0 ]
[ 38767-72-5 ]
[ 130378-91-5 ]
[ 130378-90-4 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 208 - 212

3
[ 38767-72-5 ]
[ 55290-73-8 ]

Yield	Reaction Conditions	Operation in experiment
0.22 g (67%)	With N-chloro-succinimide; In methanol; acetic acid;	EXAMPLE 13 4-Amino-3-chloro-2(1H)-pyridinone To a solution of 0.25 g (2.3 mmol) of <strong>[38767-72-5]4-amino-2(1H)-pyridinone</strong> in 5 ml of acetic acid were added 0.33 g (2.5 mmol) of N-chlorosuccinimide. The resulting solution was stirred for 2 hours and then concentrated under vacuum, coevaporating with ethanol. The residue was dissolved in methanol and 5 g of silica gel were added. The methanol was removed under vacuum, and the resulting powder charged to a 100 g column of silica gel previously packed under dichloromethane. Elution of the column with 10:1 dichloromethane-methanol yielded 0.22 g (67%) of 4-amino-3-chloro-2(1H)-pyridinone as an off-white solid, mp 264-267 C.

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011
[2]Patent: US4681873,1987,A

4
[ 38767-72-5 ]
[ 107842-74-0 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

5
[ 98007-15-9 ]
[ 38767-72-5 ]
4-Amino-1-[2,2']bipyridinyl-5-ylmethyl-1H-pyridin-2-one [ No CAS ]

Reference： [1]Chemical Communications,1997,p. 2181 - 2182

6
[ 14432-12-3 ]
[ 38767-72-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydroxide; In toluene; at 170℃; for 72h;Sealed tube;	A mixture of 2-chloro-4-aminopyridine 3 (127 mg, 1.0 mmol) and KOH (280.6mg, 5.0 mmol) in toluene (4.0 mL) was heated at 170C in a sealed tube for 72h. Themixture was cooled to r.t. and the toluene was removed. The residue was purified byflash chromatography on silica gel (DCM/MeOH/NH4OH: 78/20/2) to give 5 (107 mg,97%) as a pale yellow solid

Reference： [1]Synlett,2016,vol. 27,p. 67 - 69
[2]Tetrahedron,1999,vol. 55,p. 11985 - 11996

7
[ 10416-59-8 ]
[ 38767-72-5 ]
4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyridine [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11985 - 11996

9
[ 109-09-1 ]
[ 38767-72-5 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11985 - 11996

10
[ 2402-95-1 ]
[ 38767-72-5 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11985 - 11996

11
[ 14432-16-7 ]
[ 38767-72-5 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11985 - 11996

12
[ 626-03-9 ]
[ 38767-72-5 ]

Reference： [1]Synthesis,1984,p. 765 - 766

13
[ 38767-72-5 ]
[ 130378-88-0 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 208 - 212

14
[ 38767-72-5 ]
4-Amino-3-chloro-1-trimethylsilanyl-1H-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

15
[ 38767-72-5 ]
4-Amino-3-bromo-1-trimethylsilanyl-1H-pyridin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

16
[ 38767-72-5 ]
[ 107842-77-3 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

17
[ 38767-72-5 ]
[ 107842-75-1 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

18
[ 38767-72-5 ]
[ 107842-78-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

19
[ 38767-72-5 ]
[ 107842-76-2 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2006 - 2011

20
[ 959709-11-6 ]
[ 38767-72-5 ]
[ 1105689-92-6 ]

Yield	Reaction Conditions	Operation in experiment
49%	With 8-quinolinol; potassium carbonate;copper(l) iodide; In dimethyl sulfoxide; at 75 - 80℃; for 16h;	Example 3 Synthesis of 2-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide To a degassed solution of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (1.58 g, 5.00 mmol), <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> (0.72 g, 6.50 mmol), potassium carbonate (2.00 g, 14.40 mmol) and 8-hydroxyquinoline (0.08 g, 0.50 mmol) in dimethyl sulfoxide (30 mL) was added copper(I) iodide (0.10 g, 0.50 mmol). The reaction mixture was heated at 75-80 C. for 16 hours, then cooled to ambient temperature. Water (300 mL) was added to the mixture and the crude product was precipitated and collected by filtration. The crude product was subjected to column chromatography to afford the title compound as a white solid (0.84 g, 49%): mp 171-172 C.; 1H NMR (300 MHz, DMSO-d6) delta 8.68 (t, J=5.7 Hz, 1H), 8.40 (d, J=7.8 Hz, 1H), 7.32-7:19 (m, 5H), 6.80 (s, 2H), 6.07 (dd, J=7.8, 1.8 Hz, 1H), 5.38 (d, J=1.8 Hz, 1H), 4.37 (d, J=5.7 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, DMSO-d6) delta 162.2, 160.8, 157.7, 154.6, 150.0, 140.0, 131.5, 128.7, 127.7, 127.1, 122.9, 103.4, 90.5, 43.0, 17.5; MS (ES+) m/z 341.2 (M+1).

Reference： [1]Patent: US2009/156615,2009,A1 .Location in patent: Page/Page column 28
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 526 - 531

21
[ 65193-87-5 ]
[ 38767-72-5 ]
[ 67-63-0 ]
[ 1050477-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol;	Example 34A 2-Cyanoethyl 4-[4-bromo-2-(trifluoromethoxy)phenyl]-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate 10.00 g (31.17 mmol) of the compound from Example 6A and 6.41 g (31.17 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] are introduced into 100 ml of 2-propanol and, after adding 4.09 g (37.17 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)], stirred at the reflux temperature for three days. After cooling, the solvent is removed under reduced pressure, and the crude product is purified by column chromatography (silica gel; mobile phase: dichloromethane/methanol 10:1). 7.38 g (36% of theory) of the title compound are obtained. LC-MS (method 6): Rt=2.84 min; MS (Elpos): m/z=499 [M+H]+.

Reference： [1]Patent: US2010/136142,2010,A1

22
[ 65193-87-5 ]
[ 38767-72-5 ]
[ 1050477-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; isopropyl alcohol;	Example 20A 2-Cyanoethyl 4-(4-cyano-2-methoxyphenyl)-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate 14.63 g (90.81 mmol) of the compound from Example 10A, 10.00 g (90.81 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 15.65 g (90.81 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] are dissolved in 300 ml of isopropanol and stirred at the reflux temperature under argon for 3 days. The mixture is then concentrated and subsequently purified by column chromatography (silica gel; mobile phase: initially ethyl acetate and then dichloromethane/methanol 10:1). The resulting product fractions are concentrated and then taken up in a little ethyl acetate. The precipitated product is filtered off and dried at 40 C. in vacuo overnight. 10.11 g (27% of theory) of the title compound are obtained. LC-MS (method 6): Rt=1.83 min; MS (Elpos): m/z=391 [M+H]+ 1H-NMR (300 MHz, DMSO-d6): delta=2.27 (s, 3H), 2.79 (m, 2H), 3.75 (s, 3H), 3.96-4.14 (m, 2H), 5.19 (s, 1H), 5.87 (d, 1H), 7.10 (d, 1H), 7.23 (dd, 1H), 7.30-7.35 (m, 2H), 9.30 (s, 1H), 10.83 (s, 1H).

Reference： [1]Patent: US2010/136142,2010,A1

23
[ 65193-87-5 ]
[ 38767-72-5 ]
[ 1050477-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Example 31A 2-Cyanoethyl 2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate 3.00 g (15.94 mmol) of the compound from Example 5A, 1.75 g (15.94 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 2.47 g (15.94 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] are dissolved in 60 ml of ethanol and stirred at the reflux temperature under argon overnight. The precipitated product is then filtered off, washed with ethanol and diethyl ether and dried under high vacuum. 2.30 g (35% of theory) of the title compound are obtained in the form of beige-colored crystals. LC-MS (method 7): Rt=1.59 min; MS (Elpos): m/z=418 [M+H]+.

Reference： [1]Patent: US2010/136142,2010,A1

24
[ 21962-45-8 ]
[ 10230-68-9 ]
[ 38767-72-5 ]
[ 959984-55-5 ]

Yield	Reaction Conditions	Operation in experiment
2%	With acetic acid; In isopropyl alcohol; for 12h;Reflux;	Example 47A 3-Methoxy-4-(2-methyl-3-nitro-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)benzonitrile 688 mg (4.26 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 440 mg (4.26 mmol) of 1-nitroacetone, 470 mg (4.26 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 367 mul (6.40 mmol) of acetic acid in 10 ml of isopropanol and heated under reflux under argon for 12 h. After cooling, DMSO (5 ml) is added and the reaction solution is purified directly by preparative HPLC. 41 mg (2% of theory) of the title compound are obtained as a brown solid. LC-MS (method 1): Rt=1.30 min; [M+H]+=339.

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 27

25
[ 959984-41-9 ]
[ 38767-72-5 ]
[ 959984-42-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	In isopropyl alcohol; for 12h;Reflux; Inert atmosphere;	Example 32A 3-Acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one 1.28 g (4.24 mmol) of 3-[4-nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione and 484 mg (4.24 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 25 ml of isopropanol and heated under reflux under argon for 12 h. Cooling is followed by filtration, and the remaining solid is washed with diethyl ether (40 ml). 990 mg (58% of theory) of the title compound are obtained as a white solid. LC-MS (method 1): Rt=1.51 min; [M+H]+=394 1H-NMR (300 MHz, DMSO-d6): delta=2.15 (s, 3H), 2.32 (s, 3H), 5.58 (s, 1H), 5.92 (d, 1H), 7.15 (t, 1H), 7.63 (d, 1H), 8.17 (d, 1H), 8.29 (dd, 1H), 9.32 (s, 1H), 10.84 (d, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 23

26
[ 21962-45-8 ]
[ 38767-72-5 ]
[ 70807-22-6 ]
[ 959984-40-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetic acid; In isopropyl alcohol; for 12h;Reflux; Inert atmosphere;	Example 30A 4-(4-Cyano-2-methoxyphenyl)-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile 1.05 g (6.51 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 684 mg (6.51 mmol) of sodium 1-cyanoprop-1-en-2-olate, 789 mg (7.16 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 600 mul (9.77 mmol) of acetic acid in 30 ml of isopropanol and heated under reflux under argon for 12 h. Cooling is followed by filtration, and the remaining solid is washed with diethyl ether (40 ml). 1.96 g (94% of theory) of the title compound are obtained as a white solid. LC-MS (method 4): Rt=1.17 min; [M+H]+=319 1H-NMR (300 MHz, DMSO-d6): delta=2.01 (s, 3H), 3.83 (s, 3H), 5.02 (s, 1H), 5.94 (d, 1H), 7.03 (d, 1H), 7.19 (d, 1H), 7.32 (d, 1H), 7.45 (s, 1H), 9.88 (s, 1H), 11.06 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 22

27
[ 21962-45-8 ]
[ 1286736-41-1 ]
[ 38767-72-5 ]
[ 959984-54-4 ]

Yield	Reaction Conditions	Operation in experiment
34%	With acetic acid; In isopropyl alcohol; for 12h;Reflux; Inert atmosphere;	Example 46A 4-(4-Cyano-2-methoxyphenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile 500 mg (3.1 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 493 mg (3.1 mmol) of sodium 1-cyano-3,3,3-trifluoroprop-1-en-2-olate, 341 mg (3.1 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 266 mul (4.65 mmol) of acetic acid in 40 ml of isopropanol and heated under reflux under argon for 12 h. After cooling, the solution is concentrated, and the residue is again stirred in 45 ml of acetic acid under reflux overnight. The solution is cooled and then concentrated, and the residue is purified by preparative HPLC. 392 mg (34% of theory) of the title compound are obtained as a white solid. LC-MS (method 1): Rt=1.63 min; [M+H]+=373 1H-NMR (300 MHz, DMSO-d6): delta=3.83 (s, 3H), 5.12 (s, 1H), 6.12 (d, 1H), 7.21 (d, 1H), 7.25 (d, 1H), 7.38 (dd, 1H), 7.51 (d, 1H), 10.29 (s, 1H), 11.22 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 27

28
[ 38767-72-5 ]
[ 81764-99-0 ]
[ 959984-32-8 ]

Yield	Reaction Conditions	Operation in experiment
31%	In isopropyl alcohol; for 96h;Reflux; Inert atmosphere;	Example 19A 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)benzonitrile 1.5 g (7.04 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)benzonitrile are mixed with 0.77 g (7.04 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)], dissolved in 40 ml of isopropanol and heated under reflux under argon for 4 days. The mixture is then concentrated and the residue is recrystallized from methanol. 0.67 g (31% of theory) of the title compound is obtained as a pale yellow solid. LC-MS (method 1): Rt=1.22 min; MS (EIpos): m/z=306 [M+H]+ 1H-NMR (300 MHz, DMSO-d6): delta=2.10 (s, 3H), 2.38 (s, 3H), 5.13 (s, 1H), 5.91 (d, 1H), 7.13 (t, 1H), 7.44 (d, 2H), 7.68 (d, 2H), 9.32 (s, 1H), 11.05 (br. s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 19

29
[ 94420-03-8 ]
[ 38767-72-5 ]
[ 70807-22-6 ]
[ 959984-30-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid; In isopropyl alcohol; for 12h;Reflux; Inert atmosphere;	Example 12A 2-Methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile 300 mg (1.59 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 167.5 mg (1.59 mmol) of sodium 1-cyanoprop-1-en-2-olate, 175 mg (1.59 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 137 mul (2.39 mmol) of acetic acid in 12 ml of 2-propanol and heated under reflux under argon for 12 h. After cooling, the reaction mixture is filtered and the remaining solid is washed with diethyl ether (20 ml). 454 mg (82% of theory) of the title compound are obtained as a white solid. MS (ESI): [M+H]+=346.2 1H-NMR (300 MHz, DMSO-d6): delta=2.06 (s, 3H), 2.38 (s, 3H), 5.14 (s, 1H), 5.97 (d, 1H), 6.25 (s, 1H), 7.22 (d, 1H), 7.37 (t, 1H), 7.43 (dd, 1H), 7.87 (dd, 1H), 10.02 (s, 1H), 11.11 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 17

30
[ 959934-74-8 ]
[ 38767-72-5 ]
[ 959984-28-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	In isopropyl alcohol; for 96h;Reflux; Inert atmosphere;	Example 7A 3-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one 4.00 g (14.79 mmol) of 3-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione and 1.63 g (14.79 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 40 ml of isopropanol and heated at the reflux temperature under argon for 4 days. The mixture is then concentrated and the residue is recrystallized from methanol. 4.1 g (76% of theory) of the title compound are obtained as a yellow solid. LC-MS (method 4): Rt=1.26 min; [M+H]+=363 1H-NMR (300 MHz, DMSO-d6): delta=2.13 (s, 3H), 2.28 (s, 3H), 2.36 (s, 3H), 5.45 (s, 1H), 5.93 (d, 1H), 6.18 (s, 1H), 7.12 (m, 1H), 7.31 (t, 1H), 7.64 (dd, 1H), 7.78 (dd, 1H), 9.35 (s, 1H), 10.82 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 16

31
[ 959934-77-1 ]
[ 38767-72-5 ]
[ 959984-31-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	In isopropyl alcohol; for 96h;Reflux; Inert atmosphere;	Example 17A 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-methoxybenzonitrile 18 g (74 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile and 8.14 g (74 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 40 ml of isopropanol and heated under reflux under argon for 4 days. The mixture is then concentrated and the residue is recrystallized from methanol. 18.1 g (70% of theory) of the title compound are obtained as a pale yellow solid. LC-MS (method 4): Rt=1.46 min; MS (EIpos): m/z=336 [M+H]+ 1H-NMR (300 MHz, DMSO-d6): delta=2.14 (s, 3H), 2.15 (s, 3H), 3.79 (s, 3H), 5.32 (s, 1H), 5.92 (d, 1H), 7.10 (d, 1H), 7.14 (d, 1H), 7.27 (d, 1H), 7.37 (s, 1H), 9.18 (s, 1H), 10.90 (br. s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 18

32
[ 959984-58-8 ]
[ 38767-72-5 ]
[ 959984-29-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	In isopropyl alcohol; for 72h;Reflux;	3.32 g (10.73 mmol) of the benzylidene compound obtained in this way are dissolved in 100 ml of isopropanol and, while boiling, 1.31 g (10.73 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)], dissolved in 60 ml of hot isopropanol, are added (adding the 4-aminopyridin-21H)-one as a suspension should be avoided in this connection). After stirring at the reflux temperature for three days, the solvent is removed in a rotary evaporator, the residue is taken up in methanol, and the resulting solid is filtered off 2.40 g (57% of theory) of the title compound are obtained. LC-MS (method 4): Rt=1.72 min; MS (EIpos): m/z=390 [M+H]+ 1H-NMR (300 MHz, DMSO-d6): delta=2.12 (s, 3H), 2.27 (s, 3H), 5.29 (s, 1H), 5.89 (d, 1H), 7.14 (t, 1H), 7.58 (d, 1H), 7.65 (br. s, 1H), 7.69 (dd, 1H), 9.34 (s, 1H), 10.91 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 16-17

33
[ 959984-38-4 ]
[ 38767-72-5 ]
[ 959984-39-5 ]

Yield	Reaction Conditions	Operation in experiment
20%	In isopropyl alcohol; for 96h;Reflux; Inert atmosphere;	Example 29A 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-ethylbenzonitrile 1 g (4.14 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-ethylbenzonitrile and 0.45 g (4.14 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Scats, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 20 ml of isopropanol and stirred at the reflux temperature under argon for 4 days. The mixture is then concentrated and the residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 10:1). 277 mg (20% of theory) of the title compound are obtained as a pale yellow solid. LC-MS (method 1): Rt=1.44 min; [M+H]+=334 1H-NMR (300 MHz, CDCl3): delta=1.26 (t, 3H), 2.14 (s, 3H), 2.34 (s, 3H), 3.19 (m, 1H), 3.40 (m, 1H), 5.24 (s, 1H), 5.92 (d, 1H), 7.11 (t, 1H), 7.29 (d, 1H), 7.46 (m, 2H), 9.26 (s, 1H), 10.87 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 22

34
[ 959984-59-9 ]
[ 38767-72-5 ]
[ 959984-43-1 ]

Yield	Reaction Conditions	Operation in experiment
8.3%	In isopropyl alcohol; at 100℃; for 24h;	155 mg (0.670 mmol) of the benzylidene compound obtained in this way are taken up in 5 ml of isopropanol and, after addition of 73.8 mg (0.67 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong>, reacted in a closed vessel at a bath temperature of 100 C. for 24 h. The mixture is then concentrated and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80?95:5). 18 mg (8.3% of theory based on the intermediate 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-fluorobenzonitrile) of the title compound are obtained. LC-MS (method 4): Rt=1.49 min; [M+H]+ (EIpos): m/z=324 1H-NMR (300 MHz, DMSO-d6): delta=2.13 (s, 3H), 2.30 (s, 3H), 5.25 (s, 1H), 5.91 (d, 1H), 7.15 (t, 1H), 7.41 (t, 1H), 7.54 (d, 1H), 7.65 (d, 1H), 9.34 (s, 1H), 10.98 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 24

35
[ 959984-45-3 ]
[ 38767-72-5 ]
[ 959984-44-2 ]

Yield	Reaction Conditions	Operation in experiment
45.3%	In isopropyl alcohol; for 24h;Reflux;	403 mg (1.63 mmol) of the benzylidene compound obtained in this way are taken up in 8 ml of isopropanol, mixed with 179.2 mg (1.63 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> and heated at the reflux temperature for 24 h. The mixture is then concentrated and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80?95:5). 251 mg (45.3% of theory based on the intermediate 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile) of the title compound are obtained. LC-MS (method 4): Rt=1.57 min; [M+H]+ (EIpos): m/z=340 1H-NMR (300 MHz, DMSO-d6): delta=2.13 (s, 3H), 2.27 (s, 3H), 5.38 (s, 1H), 5.89 (d, 1H), 7.13 (t, 1H), 7.47 (d, 1H), 7.66 (dd, 1H), 7.82 (d, 1H), 9.31 (s, 1H), 10.89 (d, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 24

36
[ 959984-46-4 ]
[ 38767-72-5 ]
[ 959984-47-5 ]

Yield	Reaction Conditions	Operation in experiment
22.5%	In isopropyl alcohol; for 72h;Reflux;	Example 40A 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-methylbenzonitrile 1.10 g (4.84 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-methylbenzonitrile are taken up in 30 ml of isopropanol and, after addition of 592 mg (4.84 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong>, heated at the reflux temperature for 72 h. The mixture is then concentrated, and the residue is again taken up in isopropanol and filtered through silica gel with isopropanol as eluent. The residue after concentration of the filtrate is mixed with a little methanol and crystallized. The precipitated product is filtered off, washed with diethyl ether and dried under high vacuum. 348 mg (22.5% of theory) of the title compound are obtained. LC-MS (method 1): Rt=1.32 min; [M+H]+ (EIpos): m/z=320 1H-NMR (300 MHz, DMSO-d6): delta=2.16 (s, 3H), 2.35 (s, 3H), 2.79 (s, 3H), 5.11 (s, 1H), 5.93 (d, 1H), 7.11 (d, 1H), 7.26 (d, 1H), 7.42-7.49 (m, 2H), 9.25 (s, 1H), 10.89 (d, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 25

37
[ 959984-50-0 ]
[ 38767-72-5 ]
[ 959984-51-1 ]

Yield	Reaction Conditions	Operation in experiment
21.2%	In isopropyl alcohol; for 72h;Reflux;	Example 44A 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile 325 mg (1.23 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-1-naphthonitrile are taken up in 20 ml of isopropanol and, after addition of 151 mg (1.23 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong>, heated at the reflux temperature for 72 h. The mixture is then concentrated and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80?95:5). The product fractions are combined, the solvent is removed, and the residue is stirred with diethyl ether. The precipitated product is filtered off and dried under high vacuum. 91 mg (21.2% of theory) of the title compound are obtained. LC-MS (method 1): Rt=1.51 min; [M+H]+ (EIpos): m/z=356 1H-NMR (300 MHz, DMSO-d6): delta=2.03 (s, 3H), 2.39 (s, 3H), 5.90 (s, 1H), 5.97 (d, 1H), 7.11 (d, 1H), 7.49 (d, 1H), 7.73 (m, 2H), 8.03 (d, 2H), 9.10 (d, 1H), 9.39 (s, 1H), 10.84 (s, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 26

38
C₁₄H₁₀F₃NO₂ [ No CAS ]
[ 38767-72-5 ]
[ 959984-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; for 24h;Reflux;	500 mg of the crude mixture obtained in this way (3-trifluoromethyl-4-formylbenzonitrile content about 1 mmol), 251.4 mg (2.511 mmol) of 2,4-pentanedione, 226.2 mg (3.77 mmol) of acetic acid and 42.8 mg (0.50 mmol) of piperidine are dissolved in 20 ml of dichloromethane and heated under reflux with an inverse water trap overnight. Cooling is followed by washing twice with water, and the organic phase is dried with magnesium sulfate. The solvent is removed in a rotary evaporator. The resulting crude material (288 mg) is mixed with 592 mg (4.84 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong>, dissolved in 15 ml of isopropanol and then heated at the reflux temperature for 24 h. The mixture is then concentrated, and the residue is again taken up in isopropanol and filtered through silica gel with isopropanol as eluent. The residue after concentration of the filtrate is mixed with a little methanol, whereupon crystallization occurs. The precipitated product is filtered, washed with diethyl ether and dried under high vacuum. 50 mg (13.3% of theory based on the amount of 3-trifluoromethyl-4-formylbenzonitrile employed) of the title compound are obtained.LC-MS (method 1): Rt=1.39 min; [M+H]+ (EIpos): m/z=3741H-NMR (300 MHz, DMSO-d6): delta=2.14 (s, 3H), 2.29 (s, 3H), 5.54 (s, 1H), 5.90 (d, 1H), 7.14 (t, 1H), 7.53 (d, 1H), 7.91 (d, 1H), 7.97 (d, 1H), 9.24 (s, 1H), 10.83 (d, 1H).

Reference： [1]Patent: US2010/305052,2010,A1 .Location in patent: Page/Page column 25

39
[ 38767-72-5 ]
[ 1163176-12-2 ]

Reference： [1]Patent: US2011/46162,2011,A1

40
[ 38767-72-5 ]
[ 1163176-13-3 ]

Reference： [1]Patent: US2011/46162,2011,A1

41
[ 38767-72-5 ]
[ 1163175-80-1 ]

Reference： [1]Patent: US2011/46162,2011,A1

42
[ 38767-72-5 ]
[ 1163175-94-7 ]

Reference： [1]Patent: US2011/46162,2011,A1

43
[ 38767-72-5 ]
[ 1163175-95-8 ]

Reference： [1]Patent: US2011/46162,2011,A1

44
[ 7357-70-2 ]
[ 38767-72-5 ]
[ 22042-73-5 ]
[ 1163175-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In isopropyl alcohol;	Example 6A4-[4-(2-Hydroxyethoxy)phenyl]-2-mercapto-5-oxo-5,6-dihydro-1,6-naphthyridine-3-carbonitrile 1 g (9.08 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)], 1.509 g (9.08 mmol) of 4-(2-hydroxyethoxy)benzaldehyde and 0.909 g (9.08 mmol) of 2-cyanoethanethioamide were initially charged in 50 ml of 2-propanol, 0.78 ml (13.62 mmol) of acetic acid was added and the mixture was stirred at reflux overnight.The reaction mixture was concentrated and the crude product was subjected to chromatographic purification: Chromasil 100 C 18, 7 mum, 250×20 mm; mobile phase: water/acetonitrile/1% trifluoroacetic acid gradient; flow rate: 25 ml/min; 40 C.; detection: 210 nm.Yield: 374 mg (12% of theory)1H-NMR (400 MHz, DMSO-d6): delta=14.10 (s, 1H), 11.59 (d, 1H), 7.64-7.60 (m, 1H), 7.21 (d, 2H), 6.97 (d, 2H), 6.42 (d, 1H), 4.88 (br s, 1H), 4.06 (t, 2H), 3.75 (t, 2H).LC-MS (Method 6): Rt=0.65 min; MS (ESIpos): m/z=340 [M+H]+. (purity about 81%)

Reference： [1]Patent: US2011/46162,2011,A1 .Location in patent: Page/Page column 26

45
[ 7357-70-2 ]
[ 3920-50-1 ]
[ 38767-72-5 ]
5-Oxo-4-(1H-pyrazol-3-yl)-2-sulfanyl-5,6-dihydro-1,6-naphthyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In isopropyl alcohol; for 48h;Reflux;	Example 19A5-Oxo-4-(1H-pyrazol-3-yl)-2-sulfanyl-5,6-dihydro-1,6-naphthyridine-3-carbonitrile 573 mg (5.20 mmol) of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong>, 500 mg (5.02 mmol) of pyrazole-3-carbaldehyde and 521 mg (5.20 mmol) of 2-cyanoethanethioamide were initially charged in 25 ml of 2-propanol, 0.45 ml (7.81 mmol) of acetic acid was added and the mixture was stirred at reflux for 48 h. The precipitate was removed by filtration, and the filtrate was evaporated and reacted further without further purification.Yield: 608 mg (4percent of theory, purity about 9percent)LC-MS (Method 13): Rt=1.09 min; MS (ESIpos): m/z=272 [M+H]+.

Reference： [1]Patent: US2011/46162,2011,A1 .Location in patent: Page/Page column 29-30

46
[ 86864-60-0 ]
[ 38767-72-5 ]
[ 1229704-12-4 ]

Yield	Reaction Conditions	Operation in experiment
41%		To a solution of <strong>[38767-72-5]4-aminopyridin-2(1H)-one</strong> (Molbridge) (0.9 g, 8.17 mmol) in DMF (30 mL) was added NaH (60%, 490 mg, 12.3 mmol). The mixture was stirred at room temperature for 30 min before (2-bromoethoxy)(tert-butyl)dimethylsilane (2.15 g, 8.99 mmol) was added. The reaction mixture was heated at 78 C. for 15 h. The mixture was cooled and poured into H2O (100 mL) and extracted with ethyl acetate (350 mL). The organic layers were combined, washed with H2O (550 mL), brine (50 mL), dried over MgSO4 and concentrated. The residue was purified by flash chromatography (silica gel, 40+S, 0% to 10% MeOH in EtOAc) to give 4-amino-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyridin-2-one as a white solid (0.9 g, 41%).

Reference： [1]Patent: US2011/130398,2011,A1 .Location in patent: Page/Page column 23

47
[ 38767-72-5 ]
[ 76-05-1 ]
[ 340736-76-7 ]
N-(2-hydroxypyridin-4-yl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To compound 12b, 4-(5-trifluoromethyl-[1 ,2,4]oxadiazol-3-yl)-benzoic acid, (30 mg, 0.1 16 mmol) in DMF (387 muIota_) were added TFFH (61.4 mg, 0.232 mmol) and DIPEA (60.9 muIota_, 0.349 mmol). It was stirred at RT for 1 h before the appropriate aminopyridine (0.232 mmol) was added and the reaction was stirred at 70C for 1.5h. The reaction mixture was subjected to purification by reverse phase prep-HPLC (gradient elution, water / MeCN both containing 0.1 % TFA). Fractions containing the desired compound were combined and freeze-dried. Due to their (moderate) volatility the compounds were tested in Test 1 as TFA salts.

Reference： [1]Patent: WO2013/8162,2013,A1 .Location in patent: Page/Page column 88

48
[ 38767-72-5 ]
[ 23735-43-5 ]
[ 1453213-30-3 ]

Yield	Reaction Conditions	Operation in experiment
136 mg		Preparation Example 205 A mixture of 4-aminopyridin-2(1H)-one (400 mg) and N-methylpyrrolidone (15 mL) was ice cooled, and sodium hydride (218 mg) was added thereto followed by stirring at room temperature for 30 minutes. To the reaction mixture, (S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (1.14 g) and sodium iodide (109 mg) in that order were added followed by stirring at room temperature for 4 hours. After sodium hydride (218 mg) was added to the reaction mixture followed by stirring at 80 C. overnight. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and then the resulting mixture was saturated with sodium chloride, and extraction with methanol/chloroform was performed. An organic layer obtained was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by basic silica gel column chromatography (ethyl acetate/methanol) to give (R)-4-amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]pyridin-2(1H)-one (136 mg).

Reference： [1]Patent: US2014/142084,2014,A1 .Location in patent: Paragraph 0318

49
[ 3745-79-7 ]
[ 38767-72-5 ]
[ 1609271-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	Step 1:<strong>[38767-72-5]4-amino-2-hydroxypyridine</strong> A12a (1.5 g, 14.0 mmcl) (Aconpharm) is dissolved in anhydrous MeCN (50 mL) at RT before being treated with acid chloride Aib (10.1 g, 68.1 mmol) and DIPEA (23.7 mL, 136.2 mmol). The resulting mixture is stirred at RT overnight, and then diluted with THF (20 mL) and MeOH (10 mL). The resulting solution is treated with 1 ON NaOH (4.0 mL, 40 mmol) at RT and then is stirred for 20 mm. The mixture is filtered and rinsed with water and acetone to afford A12b.

Reference： [1]Patent: WO2014/70978,2014,A1 .Location in patent: Page/Page column 31; 32

50
[ 24424-99-5 ]
[ 38767-72-5 ]
[ 1609249-89-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In acetonitrile;Inert atmosphere;	Solid Boc20 (28 g, 130 mmol) is added to a solution of B5a1 (Aconpharm, 4.0 g, 36 mmol, Tyger) in MeCN (250 ml_). Solid DMAP (250 mg, 2.0 mmol) is added in 50 mg portions at 20 min intervals. The reaction is stirred overnight and then concentrated, diluted with 1 :1 t- BME/EtOAc and washed with 10% citric acid, saturated NaHC03 and brine. The organic layer is dried over Na2S04 and evaporated to dryness. MeOH (80 ml.) and saturated NaHC03 (40 ml.) are added and the mixture is stirred 3 d. The reaction is filtered and the filter cake is washed with MeOH. The filtrate is evaporated and the residue is taken up in EtOAc and the solution is washed with water and brine. The organic layer is dried over Na2S04 and concentrated and the product purified by Combiflash to give B5a.

Reference： [1]Patent: WO2014/70979,2014,A1 .Location in patent: Page/Page column 24

51
[ 38767-72-5 ]
[ 1609249-90-2 ]

Reference： [1]Patent: WO2014/70979,2014,A1

52
[ 38767-72-5 ]
[ 1609249-91-3 ]

Reference： [1]Patent: WO2014/70979,2014,A1

53
[ 38767-72-5 ]
[ 1609249-92-4 ]

Reference： [1]Patent: WO2014/70979,2014,A1

54
[ 38767-72-5 ]
[ 1609249-93-5 ]

Reference： [1]Patent: WO2014/70979,2014,A1

55
[ 38767-72-5 ]
[ 1609249-56-0 ]

Reference： [1]Patent: WO2014/70979,2014,A1

56
[ 38767-72-5 ]
[ 96530-75-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tert.-butylnitrite; pyridine hydrogenfluoride; at -20 - 60℃; for 3.5h;	To a cooled solution of HF-pyridine complex (70%, 13.1 mL) at 0C was slowlyadded 4-amino-2-pyridone 5 (1.85 g, 16.8 mmol). The mixture was cooled to -20Cand tBuONO (3.0 mL, 25.2 mmol) was slowly added. The reaction mixture wasstirred at -20C for 0.5h, then allowed to warm to r.t. for 2h and finally heated at 60Cfor 1h. The mixture was cooled to 0C and sat. aq. Na2CO3 was added. The aqueouslayer was extracted with ethyl acetate (5x), and the combined organic layers weredried (Na2SO4), filtered and concentrated under reduced pressure. The crude waspurified by flash chromatography on silica gel (DCM/MeOH: 95/5) to give 1a (1.14 g,60%) as a colorless solid.

Reference： [1]Synlett,2016,vol. 27,p. 67 - 69

57
[ 38767-72-5 ]
[ 103-80-0 ]
N-(2-oxo-1,2-dihydropyridin-4-yl)-2-phenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With pyridine; In N,N-dimethyl-formamide; at 20℃; for 24h;	To a mixture of pyridine (0.220 ml, 2.72 mmol) and 4-aminopyridin-2(lH)-one (0.20 g, 1.8 mmol) in DMF (2 ml) was added 2-phenylacetyl chloride (0.290 ml, 2.36 mmol). The resulting mixture was stirred at RT for 24 h, diluted with water (20 mL), stirred at 0 C for 10 minutes and filtered. The solid was washed with cold water (5 mL) followed by Et20 (5 mL) to give the title compound as a white solid (261 mg, 63%). MS (ES+) C13H12N2O2 requires: 228, found: 229 [M+H]+.

Reference： [1]Patent: WO2016/4413,2016,A2 .Location in patent: Paragraph 0219

58
[ 38767-72-5 ]
N-(1-(but-3-yn-1-yl)-2-oxo-1,2-dihydropyridin-4-yl)-2-phenylacetamide [ No CAS ]

Reference： [1]Patent: WO2016/4413,2016,A2

59
[ 38767-72-5 ]
N-(1-(4-(6-benzyl-7H-pyrrolo[2,3-c]pyridazin-3-yl)but-3-yn-1-yl)-2-oxo-1,2-dihydropyridin-4-yl)-2-phenylacetamide [ No CAS ]

Reference： [1]Patent: WO2016/4413,2016,A2

60
[ 38767-72-5 ]
N-(1-(4-(6-benzyl-7H-pyrrolo[2,3-c]pyridazin-3-yl)butyl)-2-oxo-1,2-dihydropyridin-4-yl)-2-phenylacetamide [ No CAS ]

Reference： [1]Patent: WO2016/4413,2016,A2

61
[ 571178-40-0 ]
[ 21962-45-8 ]
[ 38767-72-5 ]
allyl 4-(4-cyano-2-methoxyphenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6-hexahydro-1,6-naphthyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;Reflux;	The title compound is 4-formyl-3-methoxy-benzonitrile in the stoichiometric amount (Example 10A), 4-aminopyridine -2 (1H) - one (lit. [Searls, T., McLaughlin, LW, Tetrahedron 55, 11985-11996 (1999)) and allyl 4,4,4-trifluoro-3-oxo-butanoate (lit. [Moseley, JD, Tetrahedron Lett. 46, 3179-3181 (2005)) prepared starting from was then, first over night at reflux temperature di-hydrochloride was performed without adding the additive from ethanol synthesis of pyridine. then, the resulting first intermediate allyl 4- (4-cyano-2-methoxyphenyl) -2-hydroxy-5-oxo-2- (trifluoromethyl) -1,2,3,4,5,6- hexahydro- 1,6-naphthyridine-3-carboxylate Process Based on the literature (literature [Moseley, J.D., Tetrahedron Lett. 46, 3179-3181 (2005)] reference) and dehydrated by using acetic acid. Then, Example 29A uihap performance similar manner as triethyl orthoformate and the reaction of allyl 4 - (4-cyano-2 - methoxyphenyl) -5-ethoxy-2- (trifluoromethyl) -1 , to give a 4-dihydro-1,6-naphthyridine-3-carboxylate. Finally, cutting the allyl ester of the acid using a Wilkinson (Wilkinson) catalyst [tris (triphenylphosphine) rhodium (I) chloride], To give the title compound (see the literature [Moseley, J.D., Tetrahedron Lett. 46, 3179-3181 (2005)])

Reference： [1]Patent: KR101614164,2016,B1 .Location in patent: Paragraph 0465-0468

62
[ 21962-45-8 ]
[ 65193-87-5 ]
[ 38767-72-5 ]
[ 1050477-35-4 ]

Yield	Reaction Conditions	Operation in experiment
27%	In isopropyl alcohol; for 72h;Reflux; Inert atmosphere;	Example 10A From the compound of 14.63 g (90.81 mmol), 4 - aminopyridine -2 (1H) - one 10.00 g (90.81 mmol) (literature [Searls, T., McLaughlin, LW, Tetrahedron 55, 11985-11996 (1999)]) and 2-cyanoethyl 3-oxo-butanoate 15.65 g (90.81 mmol) (literature [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)]) isopropanol dissolved in 300 mL and stirred for 3 days at reflux temperature under argon. Then, the mixture was concentrated, purified by column chromatography (silica gel; mobile phase: 1: first ethyl acetate, then dichloromethane / methanol to 10) of the And purified it. The resulting product fractions was concentrated, then dissolved in a small amount of ethyl acetate. The precipitated product was filtered, dried under vacuum overnight at 40 . To give the title compound 10.11 g (27% of theory).

Reference： [1]Patent: KR101614164,2016,B1 .Location in patent: Paragraph 0375-0378

63
[ 94420-03-8 ]
[ 65193-87-5 ]
[ 38767-72-5 ]
[ 1050477-46-7 ]

Yield	Reaction Conditions	Operation in experiment
35%	In ethanol;Reflux; Inert atmosphere;	Example 5A of the compound from 3.00 g (15.94 mmol), 4 - aminopyridine -2 (1H) - one 1.75 g (15.94 mmol) (literature [Searls, T., McLaughlin, LW, Tetrahedron 55, 11985-11996 (1999 )]) and 2-cyanoethyl 3-oxo-butanoate 2.47 g (15.94 mmol) (literature [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] ) was dissolved in 60 mL ethanol and stirred overnight at reflux temperature under argon. Thereafter, the precipitated product was filtered, washed with ethanol and diethyl ether, and dried under high vacuum. The title compound 2.30 g (35% of theory) of the title compound in the form of beige crystals.

Reference： [1]Patent: KR101614164,2016,B1 .Location in patent: Paragraph 0430-0433

64
[ 65193-87-5 ]
[ 38767-72-5 ]
[ 220996-80-5 ]
[ 1050477-49-0 ]

Yield	Reaction Conditions	Operation in experiment
36%	In isopropyl alcohol; for 72h;Reflux;	Example 6A from the compound 10.00 g (31.17 mmol) and 2-cyanoethyl 3-oxo-butanoate 6.41 g (31.17 mmol) (literature [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)) 2-propanol in 100 mL introduced, and 4-aminopyridine -2 (1H) - one 4.09 g (37.17 mmol) (literature [Searls, T., McLaughlin, LW, Tetrahedron 55,11985-11996 (1999)) was added, stirred for 3 days at reflux temperature. After cooling, the solvent removed under reduced pressure and the crude product was purified by column chromatography and purified by (silica gel, mobile phase: 1: dichloromethane / methanol 10). To give the title compound 7.38 g (36% of theory).

Reference： [1]Patent: KR101614164,2016,B1 .Location in patent: Paragraph 0445-0448

65
[ 38767-72-5 ]
[ 141699-59-4 ]
tert-butyl-4-(4-amino-2-oxopyridine-1-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43.9%		<strong>[38767-72-5]4-amino-2-hydroxypyridine</strong> (5.1 g, 46.6 mmol) was dissolved in DMF (80 mL) under ice-cooling, and sodium hydride (2.0 g, 51.3 mmol) was slowly added to the reaction system at 0 C for 15 minutes TheCompound 1-3 (13.0 g, 46.6 mmol) was added to the reaction system and heated to 45 C overnight.After cooling, it was poured into 500 mL of water, extracted with ethyl acetate, and concentrated by dryness and separated by silica gel column chromatography to give Compound 1-4 (6.0 g) in a yield of 43.9%.

Reference： [1]Patent: CN106146468,2016,A .Location in patent: Paragraph 0088; 0089; 0094; 0095

66
4-methanesulfonyloxypiperidine-1-acetamide [ No CAS ]
[ 38767-72-5 ]
2-(4-(4-amino-2-oxopyridine-1-yl)piperidinyl) acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.6%		In the ice bath conditions,<strong>[38767-72-5]4-amino-2-hydroxypyridine</strong> (3.0 g, 27.9 mmol) was dissolved in DMF (50 mL), Sodium hydride (1. 2 g, 30. 8 mmol) was slowly added to the reaction system at 0 C for 15 minutes. And then the compound1-2 (6. 6 g, 28. Ommol) was added to the reaction system and heated to 45 C overnight. After cooling into 400mL of water,Ethyl acetate, and the residue was separated by silica gel column chromatography to give Compound 1-3 (3.6 g) in a yield of 51.6%.

Reference： [1]Patent: CN106146468,2016,A .Location in patent: Paragraph 0144; 0148; 0149

67
[ 38767-72-5 ]
5-iodocytosine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 3077 - 3090

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Precautionary Statements-General
Code	Phrase
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P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
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P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 38767-72-5 ] {[proInfo.proName]}

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[ 38767-72-5 ] Synthesis Path-Upstream 1~7

[ 38767-72-5 ] Synthesis Path-Downstream 1~67

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Amides

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Pyridines

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[ 38767-72-5 ]

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