[ CAS No. 184416-83-9 ] {[proInfo.proName]}

Name: 184416-83-9|2,3-Dichloropyridin-4-amine|98%
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SKU: A265712
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3d Animation Molecule Structure of 184416-83-9

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Quality Control of [ 184416-83-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 184416-83-9 ]

SDS Specification

Alternatived Products of [ 184416-83-9 ]

Product Details of [ 184416-83-9 ]

CAS No. :	184416-83-9	MDL No. :	MFCD01646113
Formula :	C₅H₄Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DVUKWILERQFZFC-UHFFFAOYSA-N
M.W :	163.01	Pubchem ID :	595728
Synonyms :

Calculated chemistry of [ 184416-83-9 ]

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) :	-6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	1.76
Log Po/w (WLOGP) :	1.98
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	1.63

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.45
Solubility :	0.575 mg/ml ; 0.00353 mol/l
Class :	Soluble
Log S (Ali) :	-2.19
Solubility :	1.04 mg/ml ; 0.00639 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 :	1.59

Safety of [ 184416-83-9 ]

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 [ 184416-83-9 ]

* 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 [ 184416-83-9 ]
Downstream synthetic route of [ 184416-83-9 ]

[ 184416-83-9 ] Synthesis Path-Upstream 1~7

1
[ 889865-45-6 ]
[ 184416-83-9 ]
[ 1152617-24-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2688 - 2701

2
[ 55934-02-6 ]
[ 184416-83-9 ]
[ 188577-69-7 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
[2] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690

3
[ 2402-77-9 ]
[ 184416-83-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2688 - 2701

4
[ 626-03-9 ]
[ 184416-83-9 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690

5
[ 103792-81-0 ]
[ 184416-83-9 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690

6
[ 96245-97-5 ]
[ 184416-83-9 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690

7
[ 184416-83-9 ]
[ 28443-69-8 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690

[ 184416-83-9 ] Synthesis Path-Downstream 1~17

1
[ 184416-83-9 ]
[ 28443-69-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 673,690

2
[ 55934-02-6 ]
[ 184416-83-9 ]
[ 188577-69-7 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 673,690
[2]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 673,690

3
[ 626-03-9 ]
[ 184416-83-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 673,690

4
[ 103792-81-0 ]
[ 184416-83-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 673,690

5
[ 96245-97-5 ]
[ 184416-83-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 673,690

Yield	Reaction Conditions	Operation in experiment
		Then, 3.5 g of diphenylphosphorylazide, 1.3 g of triethylamine and 30 ml of -butanol were added thereto, and the mixture was refluxed under heating for 6 hours. After cooling, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. To the residue, 20 ml of trifluoroacetic acid was added, and the mixture was stirred for 2 hours at room temperature. Then, trifluoroacetic acid was distilled off under reduced pressure, and then ethyl acetate was added. The mixture was washed sequentially with an aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained solid was washed with a mixture of isopropyl ether and n-hexane to obtain 1.3 g of the desired product as a white powder (melting point: 146 to 148 C.).

7
[ 2402-77-9 ]
[ 184416-83-9 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2688 - 2701

8
[ 889865-45-6 ]
[ 184416-83-9 ]
[ 1152617-24-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2688 - 2701

9
[ 184416-83-9 ]
tert-butyl ((1S)-1'-(3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyrazin-6-yl)-1,3-dihydrospiro[indene-2,4'-piperidin]-1-yl)carbamate [ No CAS ]
tert-butyl N-[(3S)-1'-{3-[(2,3-dichloropyridin-4-yl)amino]-1-(oxan-2-yl)-1H-pyrazolo[3,4-b]pyrazin-6-yl}-1,3-dihydrospiro[indene-2,4'-piperidin]-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With 9-[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenyl-lambda4-phosphanyl}-O-methanesulfonyl-8-methyl-8lambda4-aza-9-palladatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene-9,9-bis(ylium)-10-uid-9-olate; caesium carbonate; In toluene; at 100.0℃; for 12.0h;	A mixture of tert-butyl ((l S)-l'-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH- pyrazolo[3,4-b]pyrazin-6-yl)-l,3-dihydrospiro[indene-2,4'-piperidin]-l-yl)carbamate (350.0 mg, 555.0 pmol, from Intermediate J), <strong>[184416-83-9]2,3-dichloropyridin-4-amine</strong> (135.0 mg, 832.0 pmol, CAS 184416-83-9), XantPhos-Pd-G4 (47.6 mg, 55.4 pmol) and Cs2C03 (270.0 mg, 832.0 pmol) in PhMe (10 mL) was stirred at 100 C for 12 hours. The reaction mixture was concentrated and purified by silica gel column (EtOAc in petroleum ether = 0-30%) to give tert-butyl N-[(3S)-l'-{3-[(2,3-dichloropyridin-4-yl)amino]-l-(oxan-2-yl)-lH-pyrazolo[3,4- b]pyrazin-6-yl}-l,3-dihydrospiro[indene-2,4'-piperidin]-3-yl]carbamate (200.0 mg, 54% yield) as a yellow solid. LCMS m/z [M+H]+ = 665.1.

Reference： [1]Patent: WO2019/183367,2019,A1 .Location in patent: Paragraph 0399

10
[ 184416-83-9 ]
[ 24424-99-5 ]
C₁₅H₂₀Cl₂N₂O₄ [ No CAS ]