[ CAS No. 78607-32-6 ] {[proInfo.proName]}

Name: 78607-32-6|3-Amino-2,5-dichloropyridine|98%
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SKU: A776438
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Quality Control of [ 78607-32-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 78607-32-6 ]

SDS Specification

Alternatived Products of [ 78607-32-6 ]

Product Details of [ 78607-32-6 ]

CAS No. :	78607-32-6	MDL No. :	MFCD00204157
Formula :	C₅H₄Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OLZPJUVEGSNIJL-UHFFFAOYSA-N
M.W :	163.00	Pubchem ID :	2799999
Synonyms :

Calculated chemistry of [ 78607-32-6 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.66
TPSA :	38.91 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) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.47
Log Po/w (XLOGP3) :	1.8
Log Po/w (WLOGP) :	1.98
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	1.65

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.542 mg/ml ; 0.00333 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	0.946 mg/ml ; 0.00581 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.89
Solubility :	0.211 mg/ml ; 0.00129 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 78607-32-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 78607-32-6 ]

* 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 [ 78607-32-6 ]
Downstream synthetic route of [ 78607-32-6 ]

[ 78607-32-6 ] Synthesis Path-Upstream 1~11

1
[ 21427-62-3 ]
[ 78607-32-6 ]

Reference： [1] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[2] Science, 2013, vol. 342, # 6162, p. 1073 - 1076
[3] Patent: US4935051, 1990, A,
[4] Patent: US4713109, 1987, A,
[5] Journal of the Chemical Society, 1952, p. 2042,2044
[6] Patent: US4831148, 1989, A,
[7] Green Chemistry, 2015, vol. 17, # 2, p. 898 - 902

2
[ 21427-61-2 ]
[ 78607-32-6 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044
[2] Journal of the Chemical Society, 1952, p. 2042,2044

3
[ 90902-83-3 ]
[ 78607-32-6 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044

4
[ 75806-86-9 ]
[ 78607-32-6 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044

5
[ 5409-39-2 ]
[ 78607-32-6 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2042,2044

6
[ 78607-32-6 ]
[ 89402-43-7 ]

Reference： [1] Patent: US4831148, 1989, A,

7
[ 78607-32-6 ]
[ 103999-77-5 ]

Reference： [1] Patent: US4831148, 1989, A,
[2] Patent: US4831148, 1989, A,
[3] Patent: US4831148, 1989, A,
[4] Patent: US4831148, 1989, A,

8
[ 78607-32-6 ]
[ 103999-77-5 ]

Reference： [1] Patent: US4935051, 1990, A,

9
[ 78607-32-6 ]
[ 103999-77-5 ]

Reference： [1] Patent: US4713109, 1987, A,

10
[ 78607-32-6 ]
[ 7440-44-0 ]
[ 103999-77-5 ]

Reference： [1] Patent: US4831148, 1989, A,

11
[ 78607-32-6 ]
[ 122413-35-8 ]
[ 103999-77-5 ]

Reference： [1] Patent: US4831148, 1989, A,

[ 78607-32-6 ] Synthesis Path-Downstream 1~88

1
[ 49609-84-9 ]
[ 78607-32-6 ]
[ 866422-00-6 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241

2
[ 78607-32-6 ]
[ 90-02-8 ]
[ 96830-45-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 100 - 103
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 122 - 125

3
[ 78607-32-6 ]
[ 635-93-8 ]
[ 96830-44-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 100 - 103
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 122 - 125

4
[ 78607-32-6 ]
[ 1761-61-1 ]
[ 96830-47-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 100 - 103
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 122 - 125

5
[ 78607-32-6 ]
[ 134698-38-7 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241

6
[ 78607-32-6 ]
N-(2,5-Dichloro-pyridin-3-yl)-2-ethylamino-nicotinamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241

7
[ 78607-32-6 ]
[ 133627-14-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241

8
[ 78607-32-6 ]
[ 133627-28-8 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241

9
[ 78607-32-6 ]
[ 135794-93-3 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241

10
[ 78607-32-6 ]
[ 96830-57-8 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 100 - 103
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 122 - 125

11
[ 78607-32-6 ]
[ 96830-56-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 100 - 103
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 122 - 125

12
[ 5409-39-2 ]
[ 78607-32-6 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044

13
[ 21427-61-2 ]
[ 78607-32-6 ]

Reference： [1]Journal of the Chemical Society,1952,p. 2042,2044
[2]Journal of the Chemical Society,1952,p. 2042,2044

14
resin bound 3-[4-(3,5-dichloropyrid-4-ylcarboxamido)phenyl]-2-diazopropanoic acid [ No CAS ]
[ 78607-32-6 ]
3-[4-(3,5-dichloropyrid-4-ylcarboxamido)phenyl]-2-(2,5-dichloropyrid-3-ylamino)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 137 3-[4-(3,5-Dichloropyrid-4-ylcarboxamido)phenyl]-2-(2,5-dichloropyrid-3-ylamino)propanoic acid 3-Amino-2,5-dichloropyridine gave the title compound (1.0 mg) HPLC-MS Retention time 2.68 min; MH+ 501.

Reference： [1]Patent: US6348463,2002,B1 .Location in patent: Page column 52

15
[ 78607-32-6 ]
3-amino-5-chloro-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of trimethylchlorosilane and 1,2-dibromoethane (7:5 v/v, 0.125 ml) was added dropwise (keeping the T°C below 50°C) to a suspension of zinc powder (422 mg) in dimethylacetamide (3 ml). The mixture was stirred 20 min at room temperature then a solution of l-(t-butoxycarbonyl)-4-iodo-piperidine (1.62 g, prepared in 2 steps from l-(t-butoxycarbonyl)-piperidin-4-one according to J. Org. Chem. 2004, 5120) indimethylacetamide (3 ml) was added dropwise over 5 min (slightly exothermic). The resulting mixture was stirred at room temperature for 30 min then cannulated into a mixture of <strong>[78607-32-6]2,5-dichloro-3-aminopyridine</strong> (603 mg), copper(I) iodide (42 mg) and PdCl2(dppf) (91 mg) in dimethylacetamide (5 ml). The resulting mixture was stirred at 80°C for 3 hours, cooled to room temperature, poured into water, extracted with ethyl acetate, dried over sodium sulfate and concentrated in vacuo. The residue was subjected to silica gel chromatography (ethyl acetate: cyclohexane 3:7) to afford 3-amino-5-chloro-3',6'-dihydro-2'H-[2,4']bipyridinyl-r-carboxylic acid tert-butyl ester (535 mg) as a yellow solid. H NMR (400 MHz, CDC13) 1.4 (s, 9H), 1.8 (m, 4H), 2.6 (m, 1H), 2.8 (m, 2H), 3.7 (br s, 2H), 4.2 (m, 2H), 6.9 (s, 1H), 7.9 (s, 1H).The product thus obtained (448 mg) was treated as described in Example 1, Steps D and E to afford the title product (455 mg) as a white solid. M.p. 63-67 °C; H NMR (400 MHz, CDCI3) 1.9 (m, 2H), 2.2 (m, 4H), 2.7 (m, 1H), 3.2 (m, 2H), 3.3 (m, 2H), 6.2 (dt, J = 18, 9 Hz, 1H), 6.5 (d, J = 18 Hz, 1H), 7.1-7.3 (m, 4H), 7.7 (d, J = 5.2 Hz, 1H), 7.8 (s, 1H), 7.9 (m, 1H, NH), 8.3 (d, J = 2.4 Hz, 1H), 8.4 (d, J = 2.4 Hz, 1H), 8.6 (d, J = 4.8 Hz, 1H), 8.7 (d, J = 5.5 Hz, 1H); Retention Time HPLC 1.53 min; MS (ES+) 501/503/505 (M+H+).

Reference： [1]Patent: WO2006/3494,2006,A2 .Location in patent: Page/Page column 141-142

16
[ 78607-32-6 ]
Polytetrafluoroethylene [ No CAS ]
[ 89402-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride; hydrogen fluoride; tetrabutylammomium bromide; sodium nitrite; In sulfolane; dichloromethane;	Example P9 5-Chloro-2,3-difluoropyridine A 500 ml polytetrafluoroethylene reactor equipped with stirrer, thermometer and reflux condenser is charged with 120 g of hydrogen fluoride. A solution of 40.7 g (0.25 mol) of <strong>[78607-32-6]3-amino-2,5-dichloropyridine</strong> in 100 ml of sulfolane is added dropwise at a temperature in the range from 0° C. to +10° C. Then 20.7 g (0.3 mol) of sodium nitrite are introduced into this solution at +50° C. The resultant nitrogen is removed from the reactor through reflux condenser. Gas evolution ceases after 2 hours at +50° C. 150 ml of methylene chloride are added to the reaction mixture which is then poured into ice water. The two-phase mixture is neutralised with ammonia solution. The organic phase is separated and dried over sodium sulfate. The solvent is distilled off and then 200 ml of sulfolane, 166 g (2.879 mol) of potassium fluoride and 2 g of tetrabutylammonium bromide are added to the mixture of sulfolane and the product. This reacton mixture is stirred for 7 hours at 179° C. The product is subsequently distilled off directly from the sulfolane solution. The crude product is purified by distillation, affording the 5-chloro-2,3-difluoropyridine, b.p. 137°-139° C.

Reference： [1]Patent: US4831148,1989,A

17
[ 78607-32-6 ]
[ 942216-39-9 ]
C₂₁H₁₇Cl₂N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane;Heating / reflux;	A solution of oxalyl chloride (351 muL, 2 M in CH2Cl2, 0.702 mmol) was added to a stirred suspension of 4-[(2-methylphenoxy)acetyl]amino}benzoic acid (100 mg, 0.351 mmol) in CH2Cl2 (20 mL) followed by a few drops of DMF at room temperature under N2. The reaction was stirred at room temperature for 2 h after which time the suspension dissolved. The reaction mixture was concentrated under reduced pressure and azeotroped with toluene (10 mL). A mixture of the crude acid chloride, 2,5- dichloropyridin-3 -amine (63 mg, 0.386 mmol) and 1,4-dioxane (10 mL) was heated at reflux overnight under N2. The reaction mixture was concentrated under reduced pressure to afford the crude amide product. Separately, a mixture OfP2O5 (109.5 mg, 0.386 mmol), hexamethyldisilane (245 mg, 321 muL, 1.51 mmol) and 1,2-dichlorobenzene (1 mL) was heated at reflux for 10 min under N2 until the reaction became clear. The mixture was transferred by cannula to a suspension of the crude amide above in 1,2- dichlorobenzene (2 mL). The resulting mixture was heated at reflux under N2 for 2 days. The reaction mixture was cooled, diluted with CH2Cl2 (25 mL) and washed with saturated NaHCO3 (25 mL). The aqueous layer was extracted with CH2Cl2 (2 x 25 mL) and EtOAc (25 mL) and the combined organic extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure to afford the crude product. This was purified by flash column chromatography (Si, 30 x 130 mm, 0-10percent EtOAc in CHCl3 gradient) to afford N-[4-(6-chloro[l,3]oxazolo[5,4-b]pyridin-2-yl)phenyl]-2-(2- methylphenoxy)acetamide as a colorless solid. LCMS calc. = 394.10; found = 394.1 (M+l)+. 1H NMR (500 MHz, DMSO-d6) delta 10.49 (s, IH), 8.43 (d, J = 2.3 Hz, IH), 8.40 (d, J = 2.3 Hz, IH), 8.19 (d, J = 8.7 Hz, 2H), 7.90 (d, J = 8.7 Hz, 2H), 7.19-7.12 (m, 2H), 6.87 (m, 2H), 4.78 (s, 2H), 2.25 (s, 3H).

Reference： [1]Patent: WO2007/70173,2007,A2 .Location in patent: Page/Page column 96-97

18
[ 78607-32-6 ]
[ 19810-31-2 ]
[ 1227628-86-5 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3927 - 3936

19
[ 78607-32-6 ]
[ 75-36-5 ]
[ 1256478-46-2 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7946 - 7949

20
[ 78607-32-6 ]
[ 79-04-9 ]
[ 1256478-40-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7946 - 7949

21
[ 78607-32-6 ]
[ 623-51-8 ]
[ 439931-16-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of ethyl 2-mercaptoacetate (2.0 mL, 18.4 mmol) in water (5.03 mL, 12.27 mmol) was added NaOH (0.491 g, 12.27 mmol). The reaction was stirred at rt for 10 min. After this time a solution of 2,5-dichloropyridin-3- amine (2.0 g, 12.27 mmol) in EtOH (20 mL) was added and the reaction was heated at reflux for 4 days and cooled to rt. The resulting precipitate was filtered and washed with hexanes (50 mL) and MeOH (5 mL) to give 7-chloro-1H-pyrido- [2,3-b][1,4]thiazin-2(3H)-one as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 10.76 (1 H, d, J=0.6 Hz), 8.15 (1 H, d, J=2.2 Hz), 7.31 (1 H, d, J=2.3 Hz), 3.59 - 3.74 (2 H, m). Mass Spectrum (ESI) m/e = 201.0 (M + 1).

Reference： [1]Patent: WO2010/151737,2010,A2 .Location in patent: Page/Page column 168

22
[ 78607-32-6 ]
[ 1196698-32-4 ]

Reference： [1]Patent: WO2011/3684,2011,A1

23
[ 78607-32-6 ]
[ 1261551-76-1 ]

Reference： [1]Patent: WO2011/3684,2011,A1

24
[ 78607-32-6 ]
[ 375853-82-0 ]
3-amino-5-chloro-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester [ No CAS ]