[ CAS No. 23794-16-3 ]

Name: 23794-16-3|2-Bromo-1-(2-chloro-4-pyridyl)ethanone|95%
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Quality Control of [ 23794-16-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 23794-16-3 ]

CAS No. :	23794-16-3	MDL No. :	MFCD09702373
Formula :	C₇H₅BrClNO	Boiling Point :	321.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	234.48 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 23794-16-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.31
TPSA :	29.96 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.61
Log Po/w (XLOGP3) :	2.29
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	1.2
Log Po/w (SILICOS-IT) :	2.84
Consensus Log Po/w :	2.05

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.01
Solubility :	0.23 mg/ml ; 0.000982 mol/l
Class :	Soluble
Log S (Ali) :	-2.56
Solubility :	0.651 mg/ml ; 0.00278 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.85
Solubility :	0.0328 mg/ml ; 0.00014 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 23794-16-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 23794-16-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 23794-16-3 ]

[ 23794-16-3 ] Synthesis Path-Downstream 1~33

1
[ 14294-11-2 ]
[ 23794-16-3 ]
[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-pyridin-2-yl-amine [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2007,vol. 182,p. 7 - 14

2
[ 23794-15-2 ]
[ 23794-16-3 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2007,vol. 182,p. 7 - 14
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5028 - 5037

3
[ 948914-01-0 ]
[ 23794-16-3 ]
4-nitro-1H-indole-2-carboxylic acid N'-[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol Heating;

Reference： [1]Ashalatha; Narayana; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 12, p. 2785 - 2795]

4
[ 948914-03-2 ]
[ 23794-16-3 ]
6-nitro-1H-indole-2-carboxylic acid N'-[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In methanol Heating;

Reference： [1]Ashalatha; Narayana; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 12, p. 2785 - 2795]

5
[ 948914-04-3 ]
[ 23794-16-3 ]
7-nitro-N'-[4-(2-chloropyridin-4-yl)-1,3-thiazol-2-yl]-1H-indole-2-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In methanol Heating;

Reference： [1]Ashalatha; Narayana; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 12, p. 2785 - 2795]

6
[ 23794-16-3 ]
[ 622-52-6 ]
[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-p-tolyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol for 6h; Heating;

Reference： [1]Narayana; Vijaya Raj; Ashalatha; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 1, p. 7 - 14]

7
[ 23794-16-3 ]
[ 614-78-8 ]
[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-o-tolyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In ethanol for 6h; Heating;

Reference： [1]Narayana; Vijaya Raj; Ashalatha; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 1, p. 7 - 14]

8
[ 23794-16-3 ]
[ 4947-89-1 ]
(3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-amine [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2007,vol. 182,p. 7 - 14

9
[ 23794-16-3 ]
[ 117174-84-2 ]
(3-chloro-4-methyl-phenyl)-[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-amine [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2007,vol. 182,p. 7 - 14

10
[ 23794-16-3 ]
[ 41440-07-7 ]
[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-(3-methyl-pyridin-2-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol for 6h; Heating;

Reference： [1]Narayana; Vijaya Raj; Ashalatha; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 1, p. 7 - 14]

11
[ 23794-16-3 ]
[ 17356-08-0 ]
4-(2-chloro-pyridin-4-yl)-thiazol-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol for 6h; Heating;
	In ethanol at 70℃;

Reference： [1]Narayana; Vijaya Raj; Ashalatha; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 1, p. 7 - 14]
[2]Green, Jeremy; Cao, Jingrong; Bandarage, Upul K.; Gao, Huai; Court, John; Marhefka, Craig; Jacobs, Marc; Taslimi, Paul; Newsome, David; Nakayama, Tomoko; Shah, Sundeep; Rodems, Steve [Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5028 - 5037]

12
[ 23794-16-3 ]
[ 3696-23-9 ]
(4-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-thiazol-2-yl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In ethanol for 6h; Heating;

Reference： [1]Narayana; Vijaya Raj; Ashalatha; Kumari, N. Suchetha [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 1, p. 7 - 14]

13
[ 23794-16-3 ]
[ 1015242-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Ethyl isobutyrate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one In tetrahydrofuran at -78 - 20℃;	141.a a) 2-[2-(2-Chloro-pyridin-4-yl)-2-oxo-ethyl]-4-methyl-3-oxo-pentanoic acid ethyl ester. 2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (500 mg) is stirred in a mixture of 20 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Ethyl isobutyrate (337 mg) in 5 ml THF is added drop wise to a solution of LiHMDS (2.1 ml 1.0 M solution) in 5 ml THF at - 78 0C. After stirring for 2 hours at -78 0C 2-bromo-1-(2- chloro-pyridin-4-yl)-ethanone (see above) dissolved in 3 ml THF is added drop wise. The reaction mixture is allowed to warm to room temperature overnight. Aqueous NH4Cl solution is added and the mixture is extracted with ethyl acetate. After removal of the solvent the title compound is obtained as a pale yellow oil. 1H-NMR (400 MHz, DMSO-d6): 1.07 (d, 3H), 1.10 (d, 3H), 1.19 (t, 3H), 2.98 (sept, 1 H), 3.50- 3.68 (m, 2H), 4.13 (q, 2H), 4.33 (t, 1H), 7.84 (d, 1H), 7.96 (s, 1H), 8.63 (d, 1H). MS (ESI+) m/z: 312 [MH]+.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2008/34600, 2008, A1 Location in patent: Page/Page column 126-127

14
[ 23794-16-3 ]
4-(5-(2-chloropyridin-4-yl)-3-ethoxycarbonyl-1H-pyrrol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(2-ethoxycarbonylacetyl)piperidine-1-carboxylic acid tert-butyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one In tetrahydrofuran at 0 - 20℃; Stage #3: With ammonium acetate In ethanol at 20℃;	144.b b) 4-[5-(2-Chloro-pyridin-4-yl)-3-ethoxycarbonyl-1 H-pyrrol-2-yl]-piperidine-1 -carboxylic acid tert-butyl ester. NaH (660 mg, 14.5 mmol) is added to a solution of 4-(2-ethoxycarbonyl-acetyl)-piperidine-1- carboxylic acid tert-butyl ester in 150 ml of THF at 0 0C the mixture is allowed to react for 15 min at room temperature to give a clear solution. A solution of 3.5 g (14.9 mmol) 1-(2-chloro- pyridin-4-yl)-ethanone (free base, example 1c) in THF is added. The reaction is stirred for 1 h at 0 0C and at room temperature over night. Ice is added, followed by extraction with ethyl acetate. The combined organic layers are washed with sat. NaHCO3 and brine, dried over Na2SO4 and concentrated. The residue is dissolved in 50 ml of ethanol. After adding 4.20 g(54.5 mmol) NH4OAc the reaction is stirred at room temperature over night. Ice is added, followed by extraction with ethyl acetate. The combined organic layers are washed with sat. NaHCO3 and brine, dried over Na2SO4 and concentrated. The crude product is purified by silica gel chromatography (hexanes-ethyl acetate gradient).1H-NMR (400 MHz, DMSO-d6): 1.27 (t, 3H), 1.47 (s, 9H), 1.75-1.81 (m, 2H), 1.90-1.97 (m,2H), 2.85-2.95 (m, 2H), 3.86 (t, 1H), 4.09-4.14 (m, 2H), 4.31 (q, 2H), 7.09 (s, 1H), 7.39 (d,1H), 7.52 (s, 1H), 8.28 (d, 1 H), 9.91 (s, 1H, NH).MS (ESI+) m/z: 434 [MH]+.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2008/34600, 2008, A1 Location in patent: Page/Page column 131-132

15
[ 286440-10-6 ]
[ 23794-16-3 ]
BrCH₃OC₆H₃CON₂H₂C₃HNSC₅H₃NCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In ethanol for 10h; Heating;

Reference： [1]Vijaya Raj; Narayana; Ashalatha; Suchetha Kumari; Sarojini [European Journal of Medicinal Chemistry, 2007, vol. 42, # 3, p. 425 - 429]

16
[ 23794-16-3 ]
[ 151094-90-5 ]
C₁₀H₁₀N₃OS₂CH₂COC₅H₃NCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium acetate In methanol Heating;

Reference： [1]Ashalatha; Narayana; Vijaya Raj; Suchetha Kumari [European Journal of Medicinal Chemistry, 2007, vol. 42, # 5, p. 719 - 728]

17
[ 23794-16-3 ]
4-[4-(2-chloro(4-pyridyl))(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetone / 5 h / Heating 2: AlMe₃; NH₄Cl / toluene / Heating

Reference： [1]Subasinghe, Nalin L.; Illig, Carl; Hoffman, James; Rudolph; Wilson, Kenneth J.; Soll, Richard; Randle, Troy; Green, David; Lewandowski, Frank; Zhang, Marie; Bone, Roger; Spurlino, John; DesJarlais, Renee; Deckman, Ingrid; Molloy, Christopher J.; Manthey, Carl; Zhou, Zhau; Sharp, Celia; Maguire, Diane; Crysler, Carl; Grasberger, Bruce [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1379 - 1382]

18
[ 23794-16-3 ]
[ 933986-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: carbethoxyacetamidine hydrochloride With sodium ethanolate In ethanol at 0℃; for 0.333333h; Stage #2: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one In ethanol at 0 - 20℃; for 16h;	1.b b) 2-Amino-5-(2-chloro-pyridin-4-yl)-1 H-pyrrole-3-carboxylic acid ethyl ester2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (3.0 g, 12.8 mmol) is stirred in a mixture of 35 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Carbamimidoyl-acetic acid ethyl ester hydrochloride (4.26 g, 25.6 mmol) (Liebigs Ann. Chem. 1977, 1895) is suspended in 10 ml ethanol and cooled to 0 oC. To this mixture sodium ethoxide (1.74 g, 25.6 mmol) is added. The mixture is stirred for 20 minutes, then 2- bromo-1-(2-chloro-pyridin-4-yl)-ethanone in 10 ml ethanol is added dropwise. After stirring at r.t. for 16 hours the reaction is stopped by adding 100 ml water and the mixture is extracted with ethylacetate. The material obtained after removal of the solvent is used for further steps without purification.1H-NMR (400 MHZ1 DMSO-d6): 1.27 (t, 3H), 4.16 (q, 2H), 5.97 (s, 2H), 6.98 (d, 1 H), 7.44 (dd, 1H), 7.55 (d, 1 H), 8.14 (d, 1H), 11.1 (s, 1 H). MS (ESI+) m/z: 266 [MH]+

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/39285, 2007, A1 Location in patent: Page/Page column 18

19
[ 23794-16-3 ]
[ 56-06-4 ]
[ 933986-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In ethanol; for 16h;Heating / reflux;	To a solution of <strong>[56-06-4]2,6-diamino-4-hydroxypyrimidine</strong> (269 mg, 2.1 mmol) and sodium ethoxide (159 mg, 2.3 mmol) in 8 ml ethanol is added 2-bromo-1-(2-chloro-pyridin-4-yl)-ethanone (500 mg, 2.1 mmol) (free base prepared as described in example 1 b). The mixture is heated under reflux for 16 hours and then quenched by addition of water. The white precipitate which forms is filtered and titurated with ether to give the target molecule.1H-NMR (400 MHZ, DMSO-d6): 6.34 (s, 2H), 7.17 (s, 1H), 7.65 (d, 1 H), 7.77 (s, 1 H), 8.22 (d, 1 H), 10.41 (brs, 1 H), 11.7 (brs, 1 H). MS (ESI+) m/z: 262 [MH]+

Reference： [1]Patent: WO2007/39285,2007,A1 .Location in patent: Page/Page column 21-22

20
2-bromo-1-(2-chloro-4-pyridinyl)-ethanone hydrobromide [ No CAS ]
[ 23794-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In diethyl ether; water	1.b 2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (3.0 g, 12.8 mmol) is stirred in a mixture of 35 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Carbamimidoyl-acetic acid ethyl ester hydrochloride (4.26 g, 25.6 mmol) (Liebigs Ann. Chem. 1977, 1895) is suspended in 10 ml ethanol and cooled to 0 oC. To this mixture sodium ethoxide (1.74 g, 25.6 mmol) is added. The mixture is stirred for 20 minutes, then 2- bromo-1-(2-chloro-pyridin-4-yl)-ethanone in 10 ml ethanol is added dropwise. After stirring at r.t. for 16 hours the reaction is stopped by adding 100 ml water and the mixture is extracted with ethylacetate. The material obtained after removal of the solvent is used for further steps without purification.1H-NMR (400 MHZ1 DMSO-d6): 1.27 (t, 3H), 4.16 (q, 2H), 5.97 (s, 2H), 6.98 (d, 1 H), 7.44 (dd, 1H), 7.55 (d, 1 H), 8.14 (d, 1H), 11.1 (s, 1 H). MS (ESI+) m/z: 266 [MH]+
	With sodium hydrogencarbonate In water	141.a a) 2-[2-(2-Chloro-pyridin-4-yl)-2-oxo-ethyl]-4-methyl-3-oxo-pentanoic acid ethyl ester. 2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (500 mg) is stirred in a mixture of 20 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Ethyl isobutyrate (337 mg) in 5 ml THF is added drop wise to a solution of LiHMDS (2.1 ml 1.0 M solution) in 5 ml THF at - 78 0C. After stirring for 2 hours at -78 0C 2-bromo-1-(2- chloro-pyridin-4-yl)-ethanone (see above) dissolved in 3 ml THF is added drop wise. The reaction mixture is allowed to warm to room temperature overnight. Aqueous NH4Cl solution is added and the mixture is extracted with ethyl acetate. After removal of the solvent the title compound is obtained as a pale yellow oil. 1H-NMR (400 MHz, DMSO-d6): 1.07 (d, 3H), 1.10 (d, 3H), 1.19 (t, 3H), 2.98 (sept, 1 H), 3.50- 3.68 (m, 2H), 4.13 (q, 2H), 4.33 (t, 1H), 7.84 (d, 1H), 7.96 (s, 1H), 8.63 (d, 1H). MS (ESI+) m/z: 312 [MH]+.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/39285, 2007, A1 Location in patent: Page/Page column 18
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2008/34600, 2008, A1 Location in patent: Page/Page column 126-127

21
[ 23794-16-3 ]
[ 5699-40-1 ]
C₁₀H₁₁ClN₄O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6142 - 6146

22
[ 23794-16-3 ]
[ 68572-18-9 ]
[ 933986-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In methanol at 20℃; for 16h;

Reference： [1]Location in patent: scheme or table Schlapbach, Achim; Feifel, Roland; Hawtin, Stuart; Heng, Richard; Koch, Guido; Moebitz, Henrik; Revesz, Laszlo; Scheufler, Clemens; Velcicky, Juraj; Waelchli, Rudolf; Huppertz, Christine [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6142 - 6146]

23
[ 23794-16-3 ]
[ 621-40-9 ]
[ 1187669-37-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol for 1h; Reflux;
94%	Stage #1: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one; (3-methylphenyl)thiourea In ethanol for 1h; Heating; Reflux; Stage #2: With ammonia In ethanol; water at 0 - 20℃; for 1h;	1-87 Example 1-87 4-(2-Chloro-4-pyridinyl)-7V-(3-methylphenyl)-l,3-thiazol-2-amine (150). [0359] 4-(2-Chloro-4-pyridinyl)-7V-(3-methylphenyl)-l,3-thiazol-2-amine (150). A mixture of 2-bromo-l-(2-chloro-4-pyridinyl)ethanone (0.51 g, 2.2 mmol) and 3-methylphenylthiourea (4) (0.36 g, 2.2 mmol) in EtOH (35 mL) was stirred at reflux temperature for 1 h. The mixture was cooled to 20 0C, diluted with water (80 niL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 °C for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with EtOAc, to give amine 150 (0.62 g, 94%) as a white powder: mp (EtO Ac/pet, ether) 195-197 0C; 1H NMR δ 10.30 (s, 1 H, NH), 8.45 (br d, J= 5.1 Hz, 1 H, H-6'), 7.93 (br d, J= 1.2 Hz, 1 H, H-3'), 7.87 (dd, J= 5.2, 1.4 Hz, 1 H, H-5'), 7.84 (s, 1 H, H-5), 7.55 (br d, J= 8.0 Hz, 1 H, H-6"), 7.47 (br s, 1 H, H-2"), 7.25 (br t, J= 7.8 Hz, 1 H, H-5"), 6.82 (br d, J= 7.4 Hz, 1 H, H-4"), 2.33 (s, 3 H, CH3); 13C NMR δ 163.6, 151.0 (2), 150.3, 146.2, 144.4, 140.6, 138.1, 128.8, 122.3, 119.7, 117.6, 114.2, 109.1, 21.9; MS m/z 302.5 (MH+, 100%). Anal, calcd for Ci5Hi2ClN3S: C, 59.70; H, 4.01; N, 13.92. Found: C, 59.75; H, 4.07; N, 13.82%.

Reference： [1]Hay, Michael P.; Turcotte, Sandra; Flanagan, Jack U.; Bonnet, Muriel; Chan, Denise A.; Sutphin, Patrick D.; Nguyen, Phuong; Giaccia, Amato J.; Denny, William A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797]
[2]Current Patent Assignee: STANFORD UNIVERSITY - WO2009/114552, 2009, A1 Location in patent: Page/Page column 157-158

24
[ 23794-16-3 ]
[ 15827-84-6 ]
[ 1289555-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one; 4-aminopyridine-3-carbonitrile In ethanol for 2h; Reflux; Stage #2: With sodium hydrogencarbonate In ethanol for 4h; Reflux;	1.3 6-Aminonicotinonitnle (2 g, 16.8 mmoi) and 2-bromo-1-(2-ch]oro-4-yl)-ethanone (3.9 g, 16.8 mmol) were refluxed in ethanol (100 ml) for 2h. Pale-yellow precipitate formed. NaHC03 (2 g) was added to the cooled reaction mixture and the mixture was refluxed for another 4h. After cooling, the precipitate was filtrated, washed with water and recrystalized from ethyl acetate to give the 2-(2-chloropyridin-4-yl)-6-cyano-imidazo[1 ,2-a]pyridine (1.7 g). 1 H NMR (300 MHz, D SO~cf6) δ: 8.70 (d, 1H) 8.30 (d, 1 H) 7.63 (s, 1 H) 7.35 (d, 1H) 7.29 (d, 1 H) 7.21 (dd, 1 H) 7.14 (dd, H) ; MS (ES) miz (M+H) 255.7

Reference： [1]Current Patent Assignee: GUERBET - WO2011/45415, 2011, A2 Location in patent: Page/Page column 41

25
[ 23794-16-3 ]
[ 1312814-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5

Reference： [1]Oubrie, Arthur; Kaptein, Allard; De Zwart, Edwin; Hoogenboom, Niels; Goorden, Rianne; Van De Kar, Bas; Van Hoek, Maaike; De Kimpe, Vera; Van Der Heijden, Ruud; Borsboom, Judith; Kazemier, Bert; De Roos, Jeroen; Scheffers, Michiel; Lommerse, Jos; Schultz-Fademrecht, Carsten; Barf, Tjeerd [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 613 - 618]

26
[ 23794-16-3 ]
[ 1312814-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5

27
[ 23794-16-3 ]
[ 1312814-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C

28
[ 23794-16-3 ]
[ 1312814-67-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5

29
[ 23794-16-3 ]
[ 1354531-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C

30
[ 23794-16-3 ]
[ 1312814-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5

31
[ 23794-16-3 ]
[ 1312814-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C

32
[ 23794-16-3 ]
[ 1312814-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C

33
[ 23794-16-3 ]
[ 1312814-57-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C

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Code	Phrase
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P222	Do not allow contact with air.
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P322
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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.
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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.
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P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
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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.
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P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 23794-16-3 ]

Quality Control of [ 23794-16-3 ]

Related Doc. of [ 23794-16-3 ]

Product Details of [ 23794-16-3 ]

Calculated chemistry of of [ 23794-16-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 23794-16-3 ]

Application In Synthesis of [ 23794-16-3 ]

[ 23794-16-3 ] Synthesis Path-Downstream 1~33

Related Functional Groups of [ 23794-16-3 ]

Chlorides

Bromides

Ketones

Related Parent Nucleus of [ 23794-16-3 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 23794-16-3 ]

Related Parent Nucleus of
[ 23794-16-3 ]