[ CAS No. 329-89-5 ] {[proInfo.proName]}

Name: 329-89-5|6-Aminopyridine-3-carboxamide|97%
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Quality Control of [ 329-89-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 329-89-5 ]

Product Details of [ 329-89-5 ]

CAS No. :	329-89-5	MDL No. :	MFCD00006327
Formula :	C₆H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZLWYEPMDOUQDBW-UHFFFAOYSA-N
M.W :	137.14	Pubchem ID :	9500
Synonyms :	6-AN;SR 4388;NSC 21206

Calculated chemistry of [ 329-89-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.74
TPSA :	82.0 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) :	-6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.48
Log Po/w (XLOGP3) :	0.7
Log Po/w (WLOGP) :	-0.23
Log Po/w (MLOGP) :	-0.61
Log Po/w (SILICOS-IT) :	-0.21
Consensus Log Po/w :	0.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	4.25 mg/ml ; 0.031 mol/l
Class :	Very soluble
Log S (Ali) :	-2.0
Solubility :	1.37 mg/ml ; 0.01 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.23
Solubility :	8.15 mg/ml ; 0.0594 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 329-89-5 ]

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 [ 329-89-5 ]

* 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 [ 329-89-5 ]
Downstream synthetic route of [ 329-89-5 ]

[ 329-89-5 ] Synthesis Path-Upstream 1~16

1
[ 4214-73-7 ]
[ 468068-28-2 ]
[ 329-89-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 6 h; Heating / reflux	A stirred mixture of commercially available 2-amino-5-cyano-pyridine [CAS-No. 4214-73-7] (5.0 g, 42 mmol), hydroxylamine hydrochloride (17.5 g, 0.25 mol) and sodium carbonate (31.1 g, 0.29 mol) in water (95 mL) and ethanol (21 mL) was heated under reflux conditions for 6 h. The reaction mixture was poured into water (150 mL) and extracted with ethyl acetate (4.x.100 mL). The combined organic layers were washed with brine (150 mL), dried (MgSO₄) and evaporated.The crude product was purified by column chromatography on silica gel (ethyl acetate/MeOH/NH₄OH 4:1:0.5) and crystallization (ethyl acetate/MeOH/hexane) to yield 6-amino-nicotinamide (1.39 g) and the title compound (1.42 g, 22percent) as an off-white solid. MS (EI) 152.1 [(M)⁺]; mp 300° C.

Reference： [1] Patent: US2007/232583, 2007, A1, . Location in patent: Page/Page column 43

2
[ 4214-73-7 ]
[ 329-89-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 6 h; Heating / reflux	Example B.4 6-Amino-N-hydroxy-nicotinamidine; A stirred mixture of commercially available 2-amino-5-cyano-pyridine [CAS-No. 4214-73-71 (5.0 g, 42 mmol), hydroxylamine hydrochloride (17.5 g, 0.25 mol) and sodium carbonate (31.1 g, 0.29 mol) in water (95 ml) and ethanol (21 ml) was heated under reflux conditions for 6h. The reaction mixture was poured into water (150 ml) and extracted with ethyl acetate (4.x.100 ml). The combined organic layers were washed with brine (150 ml), dried (MgSO₄) and evaporated. The crude product was purified by column chromatography on silica gel (ethyl acetate/MeOH/NH₄OH 4:1:0.5) and crystallization (ethyl acetate/MeOH/hexane) to yield 6-amino-nicotinamide (1.39 g) and the title compound (1.42 g, 22percent) as an off-white solid. MS (EI) 152.1 [(M)⁺]; mp 300° C.

Reference： [1] Patent: US2007/72879, 2007, A1, . Location in patent: Page/Page column 14

3
[ 4214-73-7 ]
[ 329-89-5 ]

Reference： [1] Journal of the American Chemical Society, 1947, vol. 69, p. 1147,1148
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482
[3] Chemicke Listy, 1952, vol. 46, p. 770[4] Chem.Abstr., 1953, p. 11191

4
[ 6271-78-9 ]
[ 329-89-5 ]

Reference： [1] Journal of Organic Chemistry, 1948, vol. 13, p. 834
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 1479,1482

5
[ 39658-41-8 ]
[ 329-89-5 ]

Reference： [1] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 369,371; engl. Ausg. S. 377

6
[ 77837-05-9 ]
[ 329-89-5 ]

Reference： [1] Bollettino Chimico Farmaceutico, 1957, vol. 96, p. 542,543

7
[ 3670-59-5 ]
[ 329-89-5 ]

Reference： [1] Journal of Organic Chemistry, 1948, vol. 13, p. 834

8
[ 1603-41-4 ]
[ 329-89-5 ]

Reference： [1] Bollettino Chimico Farmaceutico, 1957, vol. 96, p. 542,543

9
[ 4931-47-9 ]
[ 329-89-5 ]

Reference： [1] Bollettino Chimico Farmaceutico, 1957, vol. 96, p. 542,543

10
[ 36052-24-1 ]
[ 329-89-5 ]

Reference： [1] Bollettino Chimico Farmaceutico, 1957, vol. 96, p. 542,543

11
[ 98953-23-2 ]
[ 329-89-5 ]

Reference： [1] Bollettino Chimico Farmaceutico, 1957, vol. 96, p. 542,543

12
[ 21550-48-1 ]
[ 329-89-5 ]

Reference： [1] Bollettino Chimico Farmaceutico, 1957, vol. 96, p. 542,543

13
[ 3167-49-5 ]
[ 329-89-5 ]

Reference： [1] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 369,371; engl. Ausg. S. 377

14
[ 329-89-5 ]
[ 64-17-5 ]
[ 39658-41-8 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 40, p. 5757 - 5760

15
[ 329-89-5 ]
[ 113293-71-3 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 40, p. 5757 - 5760

16
[ 329-89-5 ]
[ 132213-07-1 ]

Reference： [1] Tetrahedron Letters, 1990, vol. 31, # 40, p. 5757 - 5760

[ 329-89-5 ] Synthesis Path-Downstream 1~80

1
[ 4214-73-7 ]
[ 329-89-5 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 1147,1148
[2]Journal of the American Chemical Society,1944,vol. 66,p. 1479,1482

2
[ 329-89-5 ]
[ 174485-82-6 ]
[ 861045-34-3 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1479,1482

3
[ 329-89-5 ]
[ 865-05-4 ]
6-aminonicotinamide adenine dinucleotide [ No CAS ]

Reference： [1]Journal of Biological Chemistry,1958,vol. 233,p. 964,967

4
[ 329-89-5 ]
[ 3167-49-5 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1479,1482

5
[ 6271-78-9 ]
[ 329-89-5 ]

Reference： [1]Journal of Organic Chemistry,1948,vol. 13,p. 834

6
[ 39658-41-8 ]
[ 329-89-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1954,vol. 24,p. 369,371; engl. Ausg. S. 377

7
[ 77837-05-9 ]
[ 329-89-5 ]

Reference： [1]Bollettino Chimico Farmaceutico,1957,vol. 96,p. 542,543

8
[ 329-89-5 ]
[ 38923-13-6 ]
[ 38923-03-4 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 982 - 985

9
[ 329-89-5 ]
[ 64-17-5 ]
[ 39658-41-8 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

10
[ 329-89-5 ]
[ 607-97-6 ]
[ 87745-88-8 ]
[ 87745-84-4 ]

Reference： [1]Pharmazie,1983,vol. 38,p. 218 - 220

11
[ 329-89-5 ]
[ 607-97-6 ]
[ 87745-84-4 ]

Reference： [1]Pharmazie,1983,vol. 38,p. 218 - 220

12
[ 329-89-5 ]
[ 156973-09-0 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3726 - 3733

13
[ 329-89-5 ]
[ 119072-55-8 ]
[ 100-52-7 ]
3-tert-Butylamino-2-phenyl-imidazo[1,2-a]pyridine-6-carboxylic acid amide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,1998,vol. 37,p. 2234 - 2237

14
[ 329-89-5 ]
[ 70-11-1 ]
[ 38922-97-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 1327 - 1334

15
[ 329-89-5 ]
[ 193979-81-6 ]
3-dipropylcarbamoylmethyl-2-phenyl-imidazo[1,2-<i>a</i>]pyridine-6-carboxylic acid amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 3934 - 3941

18
[ 329-89-5 ]
NADP [ No CAS ]
[ 652-81-3 ]

Reference： [1]Journal of Biological Chemistry,1958,vol. 233,p. 964,967

19
[ 19307-74-5 ]
[ 329-89-5 ]
7-ethyl-5-phenyl-1,8-naphthyridine-3-carboxamide [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2631 - 2636

20
[ 329-89-5 ]
[ 1817-61-4 ]
5-butyl-7-ethyl-1,8-naphthyridine-3-carboxamide [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2631 - 2636

21
[ 329-89-5 ]
[ 1817-57-8 ]
7-methyl-5-phenyl-1,8-naphthyridine-3-carboxamide [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2631 - 2636

22
[ 4214-73-7 ]
[ 468068-28-2 ]
[ 329-89-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; for 6h;Heating / reflux;	A stirred mixture of commercially available 2-amino-5-cyano-pyridine [CAS-No. 4214-73-7] (5.0 g, 42 mmol), hydroxylamine hydrochloride (17.5 g, 0.25 mol) and sodium carbonate (31.1 g, 0.29 mol) in water (95 mL) and ethanol (21 mL) was heated under reflux conditions for 6 h. The reaction mixture was poured into water (150 mL) and extracted with ethyl acetate (4.x.100 mL). The combined organic layers were washed with brine (150 mL), dried (MgSO4) and evaporated.The crude product was purified by column chromatography on silica gel (ethyl acetate/MeOH/NH4OH 4:1:0.5) and crystallization (ethyl acetate/MeOH/hexane) to yield 6-amino-nicotinamide (1.39 g) and the title compound (1.42 g, 22percent) as an off-white solid. MS (EI) 152.1 [(M)+]; mp 300° C.

Reference： [1]Patent: US2007/232583,2007,A1 .Location in patent: Page/Page column 43

23
[ 329-89-5 ]
[ 955885-17-3 ]
6-[4-(4-methanesulfonyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carbonyl]-amino}-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h;	Example 15; 6-[4-(4-Methanesulfonyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carbonyl]-amino}-nicotinamide; To a solution of 4-(4-methanesulfonyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (15a) (77 mg, 0.21 mmol) in DMF (3 mL) was added Et3N (90.0 uL, 0.65 mmol), 4-aminonicotinic amide (60.0 mg, 0.44 mmol) and HATU (250 mg, 0.66 mmol). The mixture was stirred at room temperature for 3 hr. The mixture was quenched with H2O (10 mL), extracted with EtOAc (2.x.10 mL). The organic layers was washed with H2O (2.x.20 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 15-30percent EtOAc in hexanes to give colorless oil (39 mg, 38percent yield). 1H NMR (400 MHz, CDCl3) delta 8.74 (dd, J=4.42, 1.39 Hz, 1H) 8.46 (dd, J=8.34, 1.26 Hz, 1H) 7.96 (d, J=8.84 Hz, 2H) 7.52 (s, 1H) 7.42-7.50 (m, 2H) 7.15 (d, J=8.84 Hz, 2H) 3.08 (s, 3H) 2.99 (s, 2H) 1.54 (s, 6H); LCMS for C24H23N3O6S m/z 482.00 (M+H)+.
38%	With triethylamine; HATU; at 20℃; for 3h;	Example 15:; 6-[4-(4-Methanesulfonyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carbonyl]- amino}-nicotinamide; To a solution of 4-(4-methanesulfonyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (15a) (77 mg, 0.21 mmol) in DMF (3 mL) was added Et3N (90.0 uL, 0.65 mmol), 4-aminonicotinic amide (60.0 mg, 0.44 mmol) and HATU (250 mg, 0.66 mmol). The mixture was stirred at room temperature for 3 hr. The mixture was quenched with H2O (10 mL), extracted with EtOAc (2x10 mL). The organic layers was washed with H2O (2x20 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 15-30percent EtOAc in hexanes to give colorless oil (39 mg, 38percent yield). 1H NMR (400 MHz, CDCI3) delta 8.74 (dd, ./=4.42, 1.39 Hz, 1 H) 8.46 (dd, J=8.34, 1.26 Hz, 1 H) 7.96 (d, J=8.84 Hz, 2 H) 7.52 (s, 1 H) 7.42 - 7.50 (m, 2 H) 7.15 (d, ./=8.84 Hz, 2 H) 3.08 (s, 3 H) 2.99 (s, 2 H) 1.54 (s, 6 H); LCMS for C24H23N3O6S m/z 482.00 (M+H)+.

Reference： [1]Patent: US2008/280875,2008,A1 .Location in patent: Page/Page column 32
[2]Patent: WO2007/122482,2007,A1 .Location in patent: Page/Page column 47

24
[ 329-89-5 ]
C₆H₇N₃⁽¹⁺⁾O₂^(1-) [ No CAS ]

Reference： [1]Molecular Pharmacology,2000,vol. 57,p. 529 - 538

25
[ 329-89-5 ]
[ 93-97-0 ]
C₁₃H₁₁N₃O₂ [ No CAS ]

Reference： [1]Molecular Pharmacology,2000,vol. 57,p. 529 - 538

26
[ 329-89-5 ]
[ 108-24-7 ]
[ 77837-05-9 ]

Reference： [1]Molecular Pharmacology,2000,vol. 57,p. 529 - 538

27
[ 329-89-5 ]
[ 4214-73-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5837 - 5844

28
[ 329-89-5 ]
(S)-1-((R)-2-Amino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid (6-amino-pyridin-3-ylmethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3726 - 3733

29
[ 329-89-5 ]
6-amino-3-pyridinylmethyl D-3,3-diphenylalanyl-L-prolinamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3726 - 3733

30
[ 329-89-5 ]
[ 183853-45-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3726 - 3733

31
[ 329-89-5 ]
[ 183853-48-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3726 - 3733

32
[ 329-89-5 ]
(S)-1-[(R)-3-(3,4-Dichloro-phenyl)-2-phenylmethanesulfonylamino-propionyl]-pyrrolidine-2-carboxylic acid (6-amino-pyridin-3-ylmethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3726 - 3733

33
[ 329-89-5 ]
[ 87745-88-8 ]

Reference： [1]Pharmazie,1983,vol. 38,p. 218 - 220

34
[ 329-89-5 ]
[ 87745-86-6 ]

Reference： [1]Pharmazie,1983,vol. 38,p. 218 - 220

35
[ 329-89-5 ]
[ 113293-71-3 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

36
[ 329-89-5 ]
[ 132213-03-7 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

37
[ 329-89-5 ]
[ 132213-07-1 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 5757 - 5760

38
[ 1603-41-4 ]
[ 329-89-5 ]

Reference： [1]Bollettino Chimico Farmaceutico,1957,vol. 96,p. 542,543

39
[ 4931-47-9 ]
[ 329-89-5 ]

Reference： [1]Bollettino Chimico Farmaceutico,1957,vol. 96,p. 542,543

40
[ 36052-24-1 ]
[ 329-89-5 ]

Reference： [1]Bollettino Chimico Farmaceutico,1957,vol. 96,p. 542,543

41
[ 98953-23-2 ]
[ 329-89-5 ]

Reference： [1]Bollettino Chimico Farmaceutico,1957,vol. 96,p. 542,543

42
[ 21550-48-1 ]
[ 329-89-5 ]

Reference： [1]Bollettino Chimico Farmaceutico,1957,vol. 96,p. 542,543

43
[ 329-89-5 ]
6-(5-amino-pyridine-2-sulfonylamino)-nicotinic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1479,1482

44
[ 329-89-5 ]
6-(5-amino-pyridine-2-sulfonylamino)-nicotinic acid amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1479,1482

45
[ 329-89-5 ]
[ 861044-94-2 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1479,1482

46
[ 3167-49-5 ]
[ 329-89-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1954,vol. 24,p. 369,371; engl. Ausg. S. 377

47
[ 3670-59-5 ]
[ 329-89-5 ]

Reference： [1]Journal of Organic Chemistry,1948,vol. 13,p. 834

48
[ 329-89-5 ]
[ 4637-24-5 ]
2-(dimethylaminomethyleneamino)-5-(dimethylaminomethyleneaminocarbonyl)pyridine [ No CAS ]

Reference： [1]Patent: US6362191,2002,B1 .Location in patent: Page column 36

49
[ 329-89-5 ]
[ 219768-41-9 ]
6-carbamoyl-3-(2,4-dichlorobenzyl)-2-methylimidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 100℃; for 64h;	A mixture of 3-bromo-4-(2,4-dichlorophenyl)-2-butanone (2.14 g), which was synthesized according to a method described in GB205177A, and <strong>[329-89-5]<strong>[329-89-5]6-aminonicotinamid</strong>e</strong> (2.10 g) in dimethylformamide (5 ml) was stirred at 100° C. for 64 hr. After concentration of the reaction mixture, the residue was washed with water and toluene and dried to give a crude product of the object compound (2.00 g) as a brown solid. The crude product was used in the next step without further purification.

Reference： [1]Patent: US6348474,2002,B1 .Location in patent: Page column 94,95

50
[ 571188-58-4 ]
[ 329-89-5 ]
[ 571188-78-8 ]
6-Bromo-8-cyclopentyl-2-methyl-8H-pyrido[2,3-d]pyrimidin-7-one; compound with 6-methyl-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	In diethyl ether; toluene;	EXAMPLE 14 6-Bromo-8-cyclopentyl-2-methyl-8H-pyrido[2,3-d]pyrimidin-7-one; compound with 6-methyl-nicotinamide 6-Bromo-8-cyclopentyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.09 g, 3.06 mmol) and <strong>[329-89-5]6-amino-nicotinamide</strong> (2.51 g, 18 mmol) were combined in toluene (8 ml) and heated to 100° C. for 18 hours. The mixture then was diluted with dimethylsulfoxide (8 ml) and heated to 120° C. for 2 hours. The mixture then was poured into water (120 ml) with rapid stirring. Diethyl ether was added and the resulting solid was collected by filtration. This solid was washed with 1:1 warm ethyl acetate/tetrahydrofuran and dried in vacuo to provide 6-bromo-8-cyclopentyl-2-methyl-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid (0.233 g, 18percent). MS (APCI); M++1: Calc'd, 429.06, Found, 429.1. Analyses for C18H17BrN6O2:

Reference： [1]Patent: US2003/149001,2003,A1

51
[ 329-89-5 ]
[ 1171622-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine; In acetic acid;	(1) To a suspension of <strong>[329-89-5]6-amino-nicotinamide</strong> (4.45 g, 32.4 mmol) in acetic acid (100 ml) was added dropwise bromine (1.84 ml, 35.7 mmol))at room temperature. The mixture was stirred at 55° C. for 3 hours. The resulting solution was added to 750 ml of 3N aqueous sodium hydroxide. The resulting sediment was filtered, washed with water and was dried over to afford 6-amino-5-bromonicotinamide. This was used for the next step without further purification. 1H-NMR (DMSO-d6, delta); 6.77 (2H, br), 7.19 (1H, br), 7.77 (1H, br), 8.15 (1H, d, J=2.0 Hz), 8.47 (1H, d, J=2.0 Hz),

Reference： [1]Patent: US2003/119877,2003,A1

52
[ 329-89-5 ]
[ 77837-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In dimethyl sulfoxide;	EXAMPLE 10 Synthesis of 6-Acetylamino nicotinamide 6-Amino nicotinamide 13.7 g (0.1 mole) is dissolved in 100 ml of dimethylsulfoxide and acetic anhydride 14.2 ml (0.15 mole) is added to the above solution. The mixture is stirred at room temperature for 16 hours. White crystals which are formed during the reaction are isolated by filtration and are purified by washing with 0.2 N HCl and ethanol.

Reference： [1]Patent: US4258052,1981,A

53
[ 4214-73-7 ]
6-amino-N-hydroxy-nicotinamidine [ No CAS ]
[ 329-89-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; for 6h;Heating / reflux;	Example B.4 6-Amino-N-hydroxy-nicotinamidine; A stirred mixture of commercially available 2-amino-5-cyano-pyridine [CAS-No. 4214-73-71 (5.0 g, 42 mmol), hydroxylamine hydrochloride (17.5 g, 0.25 mol) and sodium carbonate (31.1 g, 0.29 mol) in water (95 ml) and ethanol (21 ml) was heated under reflux conditions for 6h. The reaction mixture was poured into water (150 ml) and extracted with ethyl acetate (4.x.100 ml). The combined organic layers were washed with brine (150 ml), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica gel (ethyl acetate/MeOH/NH4OH 4:1:0.5) and crystallization (ethyl acetate/MeOH/hexane) to yield 6-amino-nicotinamide (1.39 g) and the title compound (1.42 g, 22percent) as an off-white solid. MS (EI) 152.1 [(M)+]; mp 300° C.

Reference： [1]Patent: US2007/72879,2007,A1 .Location in patent: Page/Page column 14

54
[ 329-89-5 ]
[ 348111-64-8 ]
[ 501921-60-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1784 - 1787

55
[ 329-89-5 ]
diammonium pentachloronitrosylruthenate [ No CAS ]
[ 198835-24-4 ]

Reference： [1]Russian Journal of Inorganic Chemistry,1997,vol. 42,p. 42 - 47

56
[ 329-89-5 ]
diammonium pentachloronitrosylruthenate [ No CAS ]
2(HNC₅H₃NH₂CONH₂)⁽¹⁺⁾ pentachloronitrosoruthenate [ No CAS ]

Reference： [1]Russian Journal of Inorganic Chemistry,1997,vol. 42,p. 42 - 47

57
[ 329-89-5 ]
[ 1196875-89-4 ]
[ 1196873-75-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20 - 80℃;	Compound 14: 6-(2-(4-(cyclopropylsulfonyl)-1H-indazol-1-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamido)nicotinamide ; Compound 14A was synthesized using 4-bromo-1H-indazole and methyl 2-bromo-3-(tetrahydro-2H-pyran-4-yl)propanoate as starting material using the analogous procedure described in connection with Compound 10. A mixture (3:1) of the N-1 vs. N-2 alkylated product was obtained. Purification using flash column chromatography (4:1, hexane:ethyl acetate) gave compound 14A.Compound 14B was synthesized by treating 14A (0.4 g, 1.0 mmol) in THF-H2O (5:1, 10 mL) with 1M LiOH (3.0 mmol) at 0° C. for 15 min. and the mixture was stirred for 18 h at room temperature. The reaction mixture was acidified with 1N HCl and extracted with EtOAc. The organics were dried over Na2SO4 and concentrated under vacuum. The resulting material was dried under high vacuum prior to use in the next step.Compound 14 was synthesized from 14B (0.15 g, 0.39 mmol) which was dissolved in NMP (5 mL). To this solution was added <strong>[329-89-5]<strong>[329-89-5]6-aminonicotinamid</strong>e</strong> (0.109 g, 0.79 mmol). 2-chloro-1-methylpyridiniumidodide (0.15 g, 0.58 mmol) was subsequently added along with DIPEA (0.092 mL, 0.53 mmol) at RT and the mixture was stirred for 18 h at 80° C. The reaction mixture was cooled and partitioned between EtOAc and sat. NaCl soln. The organic layer were dried and purified by prep HPLC (Waters System: Column is SunFire C18, 5mu, 30.x.75 mm, mobile phase A: 0.05percent TFA in H2O and mobile phase B is 0.035percent TFA in acetonitrile, Solvent gradient is 30-45percent B); to afford compound 14 (158 mg). [M+H] calc'd for C24H28N5O5S, 498.3; found 498.6. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.94-1.13 (m, 2H) 1.13-1.43 (m, 5H) 1.43-1.67 (m, 2H) 2.12-2.28 (m, 1H) 2.50 (ddd, J=14.21, 10.42, 5.18 Hz, 1H) 2.93-3.22 (m, 3H) 3.79-3.95 (m, 2H) 5.89 (dd, J=9.47, 4.93 Hz, 1H) 7.48 (br. s., 1H) 7.61-7.77 (m, 2H) 7.95-8.12 (m, 2H) 8.12-8.28 (m, 2H) 8.43 (s, 1H) 8.83 (d, J=1.77 Hz, 1H) 11.32 (s, 1H).Compound 14 was subjected to chiral separation on a Berger SFC instrument using Chiralpak AD-H media eluting with 40percent MeOH to afford Compounds 107 and 108.

Reference： [1]Patent: US2009/286800,2009,A1 .Location in patent: Page/Page column 108-109

58
[ 329-89-5 ]
[ 403-29-2 ]
[ 733-02-8 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 72; 2-(4-FIuorophenyl)-3-(hydroxymethyI)imidazo [ 1 ,2-a] pyridine-6-carboxamide; 6-Aminonicotinamide (41 mg, 0.30 mmol) and 4-fluorophenacyl bromide (43 mg, 0.20 mmol) were mixed in ethanol (0.5 mL) and stirred at it over the weekend. The mixture was then heated at 70 0C overnight. 0.5 M NaOH (1.2 mL) was added slowly with stirring. The precipitate that formed was collected by centrifugation and washed with water (1.5 mL) to give the intermediate compound 2-(4-fluorophenyl)imidazo[l,2-a]pyridine-6-carboxamide. MS (ESI+) m/z 256 [M+H]+.

Reference： [1]Patent: WO2010/64020,2010,A1 .Location in patent: Page/Page column 67

59
[ 329-89-5 ]
[ 536-38-9 ]
[ 1228304-31-1 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 71; 5 2-(4-Chlorophenyl)-3-(hydroxymethyl)imidazo[l,2-a]pyridine-6-carboxamide; 6-Aminonicotinamide (41 mg, 0.30 mmol) and 4-chlorophenacyl bromide (47 mg, 0.20 mmol) were mixed in ethanol (0.5 mL) and stirred at rt over the weekend. The mixture was then heated at 70 °C overnight. 0.5 M NaOH (1.2 mL) was added slowly with stirring. The0 precipitate that formed was collected by centrifugation and washed with water (1.5 mL) to give the intermediate compound 2-(4-chlorophenyl)imidazo[l,2-a]pyridine-6-carboxamide. MS (ESI+) m/z 272, 274 [M+H]+.

Reference： [1]Patent: WO2010/64020,2010,A1 .Location in patent: Page/Page column 66-67

60
[ 329-89-5 ]
[ 4252-78-2 ]
[ 1228304-35-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 74; 2-(2,4-Dichlorophenyl)-3-(hydroxymethyl)imidazo[l,2-a]pyridine-6-carboxamide; 6-Aminonicotinamide (41 mg, 0.30 mmol) and 2,4-dichlorophenacyl chloride (45 mg, 0.20 mmol) were mixed in ethanol (0.5 mL) and stirred at rt over the weekend. The mixture was then heated at 70 °C for 2 days. 0.5 M NaOH (1.2 mL) was added slowly with stirring. The precipitate that formed was collected by centrifugation and washed with water (1.5 mL) to give the intermediate compound 2-(2,4-dichlorophenyl)imidazo[l,2-a]pyridine-6- carboxamide. MS (ESI+) m/z 306, 308 [M+H]+.

Reference： [1]Patent: WO2010/64020,2010,A1 .Location in patent: Page/Page column 68

61
[ 329-89-5 ]
[ 102429-07-2 ]
[ 1228304-33-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 73; 2-(2,4-DifluorophenyI)-3-(hydroxymethyl)imidazo[l,2-a]pyridine-6-carboxamide; 6-Aminonicotinamide (41 mg, 0.30 mmol) and 2,4-difluorophenacyl bromide (47 mg, 0.20 mmol) were mixed in ethanol (0.5 mL) and stirred at rt over the weekend. The mixture was then heated at 70 °C overnight. 0.5 M NaOH (1.2 mL) was added slowly followed by CH2Cl2 (2 mL). The aqueous phase was collected, concentrated and dried in vacuo to give the intermediate compound 2-(2,4-difluorophenyl)imidazo[l,2-a]pyridine-6-carboxamide. MS (ESI+) m/z 274 [M+H]+.

Reference： [1]Patent: WO2010/64020,2010,A1 .Location in patent: Page/Page column 67-68

62
[ 329-89-5 ]
[ 5000-65-7 ]
[ 1228304-30-0 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 70; S^Hydroxymethyl^-beta-methoxyphenytyimidazotl^-alpyridine-beta-carboxamide; 6-Aminonicotinamide (41 mg, 0.30 mmol) and 2-bromo-3'-methoxyacetophenone (46 mg, 0.20 mmol) were mixed in ethanol (0.5 mL) and stirred at rt over the weekend. Theo mixture was then heated at 70 0C for 2 h. 0.5 M NaOH (1.2 mL) was added slowly with stirring. The precipitate that formed was collected by centrifugation and washed with water (1.5 mL) to give the intermediate 2-(3-methoxyphenyl)imidazo[l,2-a]pyridine-6- carboxamide. MS (ESI+) m/z 268 [M+H]+.

Reference： [1]Patent: WO2010/64020,2010,A1 .Location in patent: Page/Page column 66

63
[ 329-89-5 ]
[ 40706-98-7 ]
[ 1228304-36-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 75; 2-(3,4-Difluorophenyl)-3-(hydroxymethyl)imidazo[l,2-a]pyridine-6-carboxamide; 6-Aminonicotinamide (41 mg, 0.30 mmol) and 2-bromo-3',4'-difluoroacetophenone (47G mg, 0.20 mmol) were mixed in ethanol (0.5 mL) and stirred at rt over the weekend. The mixture was then heated at 70 °C overnight. 0.5 M NaOH (1.2 mL) was added slowly with stirring. The precipitate that formed was collected by centrifugation and washed with water (1.5 mL) to give the intermediate compound 2-(3,4-difIuorophenyl)imidazo[l,2-a]pyridine- 6-carboxamide. MS (ESI+) m/z 274 [M+H]+. s

Reference： [1]Patent: WO2010/64020,2010,A1 .Location in patent: Page/Page column 69

64
[ 329-89-5 ]
[ 935850-47-8 ]
6-{2-[2-(3,4-Dimethoxy-benzyl)-3-oxo-2,3,4,5,6,7-hexahydro-1H-isoindol-1-ylsulfanyl]-acetylamino}-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		Example 13; 6-{2-[2-(3,4-Dimethoxy-benzyl)-3-oxo-2,3,4,5,6,7-hexahydro-1H-isoindol-1-ylsulfanyl]-acetylamino}-nicotinamide; The product from Example 9, Part A (240 mg, 0.64 mmol) and <strong>[329-89-5]<strong>[329-89-5]6-aminonicotinamid</strong>e</strong> (132 mg, 0.96 mmol) were converted to the title compound by the method described in Example 4, Part C, without HOBt (25 mg, 8percent). 1H NMR (400 MHz, CDCl3) delta 9.53 (s, 1H), 8.79 (s, 1H), 8.20 (m, 2H), 6.82 (m, 3H), 5.06 (d, J=15 Hz, 1H), 4.68 (s, 1H), 4.14 (d, J=15 Hz, 1H), 3.84 (s, 6H), 3.07 (s, 2H), 2.46 (m, 1H), 2.22 (m, 3H), 1.62 (m, 4H). MS: m/z (MH+) 497.

Reference： [1]Patent: US2007/117808,2007,A1 .Location in patent: Page/Page column 21

65
[ 329-89-5 ]
[ 935850-65-0 ]
6-{2-[2-(4-Fluorobenzyl)-3-oxo-2,3,4,5,6,7-hexahydro-1H-isoindol-1-ylsulfanyl]-acetylamino}-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		C. 6-{2-[2-(4-Fluorobenzyl)-3-oxo-2,3,4,5,6,7-hexahydro-1H-isoindol-1-ylsulfanyl]-acetylamino}-nicotinamide:; The product from Part B (350 mg, 1.1 mmol) and <strong>[329-89-5]<strong>[329-89-5]6-aminonicotinamid</strong>e</strong> (220 mg, 1.6 mmol) were converted to the title compound by the method described in Example 4, Part C, without HOBt. 1H NMR (400 MHz, CDCl3) delta 9.11 (s, 1H), 8.76 (s, 1H), 8.23 (d, J=8 Hz, 1H), 8.15 (d, J=8 Hz, 1H), 7.23 (m, 2H), 6.99 (t, J=8 Hz, 2H), 6.2 (br s, 2H), 5.06 (d, J=15 Hz, 1H), 4.67 (s, 1H), 4.19 (d, J=15 Hz, 1H), 3.01 (s, 2H), 2.44 (m, 1H), 2.23 (m, 2H), 2.15 (m, 1H), 1.62 (m, 4H). MS: m/z (MH+) 455.

Reference： [1]Patent: US2007/117808,2007,A1 .Location in patent: Page/Page column 23

66
[ 329-89-5 ]
[ 931-53-3 ]
[ 13246-46-3 ]
[ 1251607-07-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With montmorillonite clay K10; In 1,4-dioxane; at 110℃; for 40h;	6-Aminonicotinamide (0.500 g, 3.64 mmol), 2,4-bis(benzyloxy)benzaldehyde (1.160 g, 3.64 mmol), cyclohexyl isocyanide (0.398 g, 3.64 mmol) and K10 (0.50 g) was dissolved in 1,4-dioxane (20 mL) at rt. The reaction mixture was refluxed for 40 h at 110 °C while monitoring the reaction progress with TLC. After work-up of the reaction as described previously, the residue obtained was subjected column chromatography on silica gel (ethyl acetate) to furnish a yellow compound which was crystallized from hexane to give pure desired product 2-(2,4-bis(benzyloxy)phenyl)-3-(cyclohexylamino)imidazo[1,2-a]pyridine-6-carboxamide 7 (1.70 g, 85percent) as a yellow solid. Mp = 112-115 °C; IRnumax (cm-1) = 2924, 1667, 1607, 1504, 1452, 1366; 1H NMR (300 MHz, CDCl3) delta 8.75 (s, 1H), 7.80 (d, J = 9.1, 1H), 7.49-7.27 (m, 12H), 6.81-6.72 (m, 2H), 6.52 (br s, 1H), 5.08 (s, 2H), 5.05 (s, 2H), 3.88 (d, J = 8.1, 1H), 2.71-2.55 (m, 1H), 1.68-1.40 (m, 5H), 1.13-0.83 (m, 5H); 13C NMR (75 MHz, CDCl3) delta 167.8, 159.9, 156.2, 141.7, 136.7, 136.0, 135.0, 132.6, 128.8, 128.7, 128.5, 128.2, 127.8, 127.7, 124.9, 121.6, 118.3, 117.2, 116.4, 107.4, 101.6, 71.7, 70.3, 56.6, 34.0, 25.7, 24.8; HRMS (m/z) calculated for C34H35N4O3, (M + H), 547.2709, found 547.2707.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4573 - 4583

67
[ 329-89-5 ]
[ 100-52-7 ]
[ 1228040-46-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 4438 - 4444

68
[ 329-89-5 ]
[ 100-52-7 ]
[ 5350-40-3 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 4438 - 4444

69
[ 329-89-5 ]
[ 1885-14-9 ]
[ 1313036-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In tetrahydrofuran; acetonitrile; at 20℃; for 2.5h;Cooling with ice;	<Step 1> Synthesis of phenyl N-(6-carbamoylpyridine-3-yl) carbamateUnder ice cooling, a tetrahydrofuran solution (3 mL) of phenyl chloroformate (0.62 mL) was added to a tetrahydrofuran-acetonitrile solution (1:2, 9 mL) of <strong>[329-89-5]<strong>[329-89-5]6-aminonicotinamid</strong>e</strong> (0.61 g) and pyridine(0.40 mL), and the mixture was stirred for 0.5 hours.The mixture was stirred at room temperature for further 2 hours.The solid precipitated was taken out by filtration and washed with ethyl acetate to give the title compound (0.84 g) as a pale yellow solid.

Reference： [1]Patent: EP2518064,2012,A1 .Location in patent: Page/Page column 64

70
[ 329-89-5 ]
[ 58092-40-3 ]
[ 76-05-1 ]
[ 651310-83-7 ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared by method B. lH NMR (500 MHz, CDCl3): delta 9.96 (1H, s), 8.87 (1H, s), 8.71 (1H, dd, 9.1 Hz, 1.5 Hz), 8.11 (2H, dd, 8.2 Hz, 1.2 Hz), 7.81 (1H, d, 9.1 Hz), 7.74 (1H, t, 7.6 Hz), 7.61 (2H, m), 5.92 (1H, s), 2.66 (3H, s). Method B: In an one dram vial fitted with a TEFLON® lined cap, substituted 2-aminopyridine (0.6mmol) was dissolved in 400mul DMF at room temperature and 2-arylsulfony1-3,3-bis-methylsulfanyl-acrylonitrile 4 in dimethylformamide (120mul, 0.12mmol) was added. The reaction mixture was subjected to heating at 80°C in a metal heating block with shaking overnight. After cooling to room temperature, the reaction mixture was further diluted with DMF and/or MeOH and subjected directly to reverse phase preparative HPLC using TFA (trifiuoroacetic acid, 0.1percent) buffered MeOH/H2O mixture as the eluent. The product was collected after fractions were concentrated in vacuo.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1782 - 1790

71
[ 329-89-5 ]
[ 361473-14-5 ]
[ 1586822-71-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	General procedure: To a stirred solution of the amine (0.169mmol), the carboxylic acid (5?22, 0.154mmol), and with or without DMAP (0.154mmol) in DCM (10mL) at room temperature was added EDCI (0.308mmol). The reaction mixture was stirred overnight and then concentrated in vacuo. The crude material was purified by flash chromatography (EtOAc/hexane) to afford the desired product (23?152, 169, 170, 175, 176).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 414 - 426

72
[ 500-22-1 ]
[ 329-89-5 ]
1-(4-(isocyanomethyl)phenyl)-2,3-di-Boc-guanidine [ No CAS ]
(Z)-3-((4-(2,3-di-Boc-guanidino)benzyl)amino)-2-(pyridin-3-yl)-imidazo[1,2-a]pyridine-6-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9238 - 9257

73
[ 329-89-5 ]
C₁₅H₁₃F₃IN₃O₂ [ No CAS ]
6-amino-N-[(7S)-5-[3-(fluoromethyl)-4-(trifluoromethyl)phenyl]-7-methyl-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazin-3-yl]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/16395,2016,A1

74
[ 329-89-5 ]
C₁₅H₁₃F₃IN₃O₂ [ No CAS ]
6-amino-N-[(7S)-5-[3-(hydroxymethyl)-4-(trifluoromethyl)phenyl]-7-methyl-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazin-3-yl]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/16395,2016,A1 .Location in patent: Page/Page column 128; 129

75
[ 329-89-5 ]
6-chloro-1-(4-methoxybenzyl)-2-(3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine [ No CAS ]
C₂₇H₂₁F₃N₆O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4213 - 4227

76
[ 329-89-5 ]
[ 100-51-6 ]
[ 13426-20-5 ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 3044 - 3049

77
[ 329-89-5 ]
6-(benzenesulfonylcarbamoyl)-3-(2,4-dichlorobenzyl)-2-methylimidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Patent: US6348474,2002,B1

78
[ 329-89-5 ]
6-carboxy-3-(2,4-dichlorobenzyl)-2-methylimidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Patent: US6348474,2002,B1

79
[ 329-89-5 ]
3-(2,4-dichlorobenzyl)-2-methyl-6-(1-n-pentanesulfonylcarbamoyl)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Patent: US6348474,2002,B1

80
[ 329-89-5 ]
[ 105-13-5 ]
[ 1494954-89-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With water; palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In n-heptane at 120℃; for 17h; Sealed tube;

Reference： [1]Azumaya, Isao; Hikawa, Hidemasa; Kikkawa, Shoko; Nakayama, Taku [RSC Advances, 2021, vol. 11, # 37, p. 23144 - 23150]

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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.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
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

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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
H227	Combustible liquid
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. 329-89-5 ] {[proInfo.proName]}

Quality Control of [ 329-89-5 ]

Related Doc. of [ 329-89-5 ]

Product Details of [ 329-89-5 ]

Calculated chemistry of [ 329-89-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 329-89-5 ]

Application In Synthesis of [ 329-89-5 ]

[ 329-89-5 ] Synthesis Path-Upstream 1~16

[ 329-89-5 ] Synthesis Path-Downstream 1~80

Related Functional Groups of [ 329-89-5 ]

Amides

Amines

Related Parent Nucleus of [ 329-89-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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Inquiry

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[ 329-89-5 ]

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[ 329-89-5 ]