[ CAS No. 1361224-53-4 ] {[proInfo.proName]}

Name: 1361224-53-4|(S)-2-(4-(4-((6-Aminopyridin-3-yl)sulfonyl)-2-(prop-1-yn-1-yl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol|99%
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SKU: A491672
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Quality Control of [ 1361224-53-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1361224-53-4 ]

SDS Specification

Alternatived Products of [ 1361224-53-4 ]

Product Details of [ 1361224-53-4 ]

CAS No. :	1361224-53-4	MDL No. :	MFCD28386194
Formula :	C₂₁H₂₀F₆N₄O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SIFKNECWLVONIH-INIZCTEOSA-N
M.W :	522.46	Pubchem ID :	73053709
Synonyms :		Chemical Name :	(S)-2-(4-(4-((6-Aminopyridin-3-yl)sulfonyl)-2-(prop-1-yn-1-yl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Calculated chemistry of [ 1361224-53-4 ]

Physicochemical Properties

Num. heavy atoms :	35
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.38
Num. rotatable bonds :	6
Num. H-bond acceptors :	11.0
Num. H-bond donors :	2.0
Molar Refractivity :	121.3
TPSA :	108.14 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.46
Log Po/w (XLOGP3) :	3.1
Log Po/w (WLOGP) :	5.7
Log Po/w (MLOGP) :	1.95
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	3.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.89
Solubility :	0.00673 mg/ml ; 0.0000129 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.04
Solubility :	0.00478 mg/ml ; 0.00000914 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.17
Solubility :	0.00352 mg/ml ; 0.00000673 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.08

Safety of [ 1361224-53-4 ]

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 [ 1361224-53-4 ]

* 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 [ 1361224-53-4 ]

[ 1361224-53-4 ] Synthesis Path-Downstream 1~24

1
[ 289483-92-7 ]
[ 1361224-72-7 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1

2
[ 504-29-0 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1

3
[ 6684-39-5 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1
[2]Patent: WO2013/123444,2013,A1
[3]Nature,2013,vol. 504,p. 437 - 440

4
[ 1361224-48-7 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Chiralpak ADH column; In methanol; carbon dioxide;Resolution of racemate;Purification / work up;	The individual enantiomers were isolated using chiral SFC. The method used was as follows: Chiralpak ADH column (21 x 250 mm, 5 muiotaeta) using 35% methanol in supercritical C02 (total flow was 70 mL/min). This produced the two enantiomers with enantiomeric excesses greater than 98%.2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(l -propyn- 1-yl)- 1 - piperazinyl)phenyl)- 1,1,1 ,3 ,3 ,3 -hexafluoro-2-propanol and 2-(4-((2R)-4-((6- amino-3 -pyridinyl)sulfonyl)-2-( 1 -propyn- 1 -yl)- 1 -piperazinyl)phenyl)- 1,1,1,3,3,3- hexafluoro-2-propanol.FIRST ELUTING PEAK (PEAK No.1)1H NMR (400 MHz, CDC13) delta 8.48 (d, J= 2.3 Hz, 1 H), 7.77 (dd, J= 2.5, 8.8 Hz, 1 H), 7.57 (d, J= 8.8 Hz, 2 H), 6.95 (d, J= 9.2 Hz, 2 H), 6.52 (d, J= 8.8 Hz, 1 H), 4.94 (s, 2 H), 4.44 (br. s., 1 H), 3.82 - 3.71 (m, 2 H), 3.58 - 3.33 (m, 3 H), 2.81 (dd, J= 3.2, 11.1 Hz, 1 H), 2.67 (dt, J= 3.9, 11.0 Hz, 1 H), 1.78 (d, J = 2.2 Hz, 3 H). m/z (ESI, +ve ion) 523.2 (M+H)+. GK-GKRP IC50 (Binding) = 0.002 muMu.SECOND ELUTING PEAK (PEAK No.2) 1H NMR (400 MHz, CDC13) delta 8.49 (d, J= 1.8 Hz, 1 H), 7.78 (dd, J= 2.3, 8.8 Hz, 1 H), 7.59 (d, J= 8.6 Hz, 2 H), 6.97 (d, J= 9.0 Hz, 2 H), 6.54 (d, J= 8.8 Hz, 1 H), 4.97 (s, 2 H), 4.46 (br. s., 1 H), 3.77 (t, J= 11.7 Hz, 2 H), 3.67 (br. s., 1 H), 3.51 - 3.33 (m, 2 H), 2.82 (dd, J= 3.3, 11.0 Hz, 1 H), 2.68 (dt, J= 3.9, 11.1 Hz, 1 H), 1.79 (d, J= 2.0 Hz, 3 H). m/z (ESI, +ve ion) 523.2 (M+H)+. GK-GKRP IC50 (Binding) = 0.342 muMu.
	With Chiralpak ADH column; In methanol;Resolution of racemate;	The individual enantiomers were isolated using chiral SFC. The method used was as follows: Chiralpak ADH column (21 x 250 mm, 5 muiotaeta) using 35% methanol in supercritical C02 (total flow was 70 mL/min). This produced the two enantiomers with enantiomeric excesses greater than 98%. 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(l -propyn- 1-yl)- 1 - piperazinyl)phenyl)- 1,1,1 ,3 ,3 ,3 -hexafluoro-2-propanol and 2-(4-((2R)-4-((6- amino-3 -pyridinyl)sulfonyl)-2-( 1 -propyn- 1 -yl)- 1 -piperazinyl)phenyl)- 1,1,1,3,3,3- hexafluoro-2-propanol. FIRST ELUTING PEAK (PEAK 1) 1H NMR (400 MHz, CDC13) delta ppm 8.48 (d, J= 2.3 Hz, 1 H), 7.77 (dd, J= 2.5, 8.8 Hz, 1 H), 7.57 (d, J= 8.8 Hz, 2 H), 6.95 (d, J= 9.2 Hz, 2 H), 6.52 (d, J= 8.8 Hz, 1 H), 4.94 (s, 2 H), 4.44 (br. s., 1 H), 3.82 - 3.71 (m, 2 H), 3.58 - 3.33 (m, 3 H), 2.81 (dd, J= 3.2, 11.1 Hz, 1 H), 2.67 (dt, J= 3.9, 11.0 Hz, 1 H), 1.78 (d, J = 2.2 Hz, 3 H). m/z (ESI, +ve ion) 523.2 (M+H)+. SECOND ELUTING PEAK (PEAK 2) 1H NMR (400 MHz, CDC13) delta ppm 8.49 (d, J= 1.8 Hz, 1 H), 7.78 (dd, J = 2.3, 8.8 Hz, 1 H), 7.59 (d, J= 8.6 Hz, 2 H), 6.97 (d, J= 9.0 Hz, 2 H), 6.54 (d, J = 8.8 Hz, 1 H), 4.97 (s, 2 H), 4.46 (br. s., 1 H), 3.77 (t, J= 11.7 Hz, 2 H), 3.67 (br. s., 1 H), 3.51 - 3.33 (m, 2 H), 2.82 (dd, J= 3.3, 11.0 Hz, 1 H), 2.68 (dt, J = 3.9, 11.1 Hz, 1 H), 1.79 (d, J= 2.0 Hz, 3 H). m/z (ESI, +ve ion) 523.2 (M+H)+.
	With Chiralpak ADH column; In methanol;	The individual enantiomers were isolated using chiral SFC (Chiralpak ADH column (21 x 250mm, 5 mm) eluting with 35% methanol in supercritical CO2 (total flow was 70 ml min-1).This produced the two analogues with enantiomeric excesses of >98%. The analytical data for 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulphonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (AMG-3969, first eluting peak) are listed below. 1H-NMR (400 MHz, CDCl3) delta 8.48 (d,J=52.3 Hz, 1 H), 7.77 (dd, J=52.5, 8.8 Hz, 1 H), 7.57 (d, J=58.8 Hz, 2 H), 6.95 (d,J=59.2 Hz, 2 H), 6.52 (d, J=58.8 Hz, 1 H), 4.94 (s, 2 H), 4.44 (br s, 1 H), 3.82-3.71 (m, 2 H), 3.58-3.33 (m, 3 H), 2.81 (dd, J=53.2, 11.1Hz, 1H), 2.67 (dt, J=53.9, 11.0 Hz,1 H), 1.78 (d, J=52.2 Hz, 3 H); m/z (ESI, positive ion) 523.2 (M+H)+.

Reference： [1]Patent: WO2012/27261,2012,A1 .Location in patent: Page/Page column 540; 541
[2]Patent: WO2013/123444,2013,A1 .Location in patent: Page/Page column 80; 81
[3]Nature,2013,vol. 504,p. 437 - 440

5
[ 1361224-49-8 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1
[2]Patent: WO2012/27261,2012,A1
[3]Patent: WO2013/123444,2013,A1
[4]Nature,2013,vol. 504,p. 437 - 440

6
[ 1361224-50-1 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1
[2]Patent: WO2012/27261,2012,A1
[3]Patent: WO2013/123444,2013,A1
[4]Nature,2013,vol. 504,p. 437 - 440

7
[ 1361224-51-2 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1
[2]Patent: WO2012/27261,2012,A1
[3]Patent: WO2013/123444,2013,A1
[4]Nature,2013,vol. 504,p. 437 - 440

8
[ 1361224-52-3 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1
[2]Patent: WO2013/123444,2013,A1
[3]Nature,2013,vol. 504,p. 437 - 440

9
[ 1361224-72-7 ]
[ 1361224-54-5 ]
[ 1361224-53-4 ]

Reference： [1]Patent: WO2012/27261,2012,A1
[2]Patent: WO2013/123444,2013,A1
[3]Nature,2013,vol. 504,p. 437 - 440

10
[ 1361224-53-4 ]
[ 1450621-61-0 ]

Yield	Reaction Conditions	Operation in experiment
75 mg	With quinoline; hydrogen; palladium(II) hydroxide; In ethanol; at 20℃; for 1.0h;Inert atmosphere;	To a degassed solution of 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2- (1 -propyn- 1 -yl)- 1 -piperazinyl)phenyl)- 1,1,1 ,3 ,3 ,3-hexafluoro-2-propanol (200 mg, 0.383 mmol, Intermediate P) and quinoline (0.045 mL, 0.383 mmol, Alfa- Aesar, Ward Hill, MA) in EtOH (50 ml) under argon at rt was added palladium hydroxide (53.8 mg, 0.077 mmol, Sigma- Aldrich, St. Louis, MO). The reaction was evacuated and flushed with hydrogen three times before stirring under a balloon of hydrogen for lh. After that time, the reaction was filtered through a pad of diatomaceous earth, washing with EtOH and the filtrate was concentrated. The resulting product was purified via column chromatography on silica gel (0 to 100% EtOAc in hexanes) to give 2-(4-((2S)-4-((6-amino-3- pyridinyl)sulfonyl)-2-(( 1 Z)- 1 -propen- 1 -yl)- 1 -piperazinyl)phenyl)- 1,1,1,3,3,3- hexafluoro-2-propanol (75 mg). 1H NMR (400 MHz, MeOD) delta ppm 8.37 - 8.20 (m, 1 H), 7.74 (dd, J= 2.4, 8.9 Hz, 1 H), 7.54 (d, J= 8.8 Hz, 2 H), 7.00 (d, J= 9.0 Hz, 2 H), 6.65 (d, J= 9.0 Hz, 1 H), 5.73 - 5.46 (m, 2 H), 4.70 - 4.52 (m, 1 H), 3.57 - 3.47 (m, 1 H), 3.41 - 3.36 (m, 2 H), 3.30 - 3.24 (m, 1 H), 3.08 - 2.93 (m, 1 H), 2.93 - 2.76 (m, 1 H), 1.64 (d, J = 5.7 Hz, 3 H). m/z (ESI, +ve ion) 525.0 (M+H)+. GK-GKRP IC50 (Binding) = 0.095 muMu.

Reference： [1]Patent: WO2013/123444,2013,A1 .Location in patent: Page/Page column 167; 168

11
[ 1450620-20-8 ]
[ 1361224-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 325 - 338

12
[ 1526937-49-4 ]
[ 1361224-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 325 - 338

13
C₁₅H₁₈N₂O₃ [ No CAS ]
[ 1361224-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 325 - 338

14
C₁₇H₁₆F₆N₂O₃ [ No CAS ]
[ 1361224-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 325 - 338

15
[ 1361224-49-8 ]
[ 1361224-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 325 - 338

16
[ 1361224-50-1 ]
[ 1361224-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 325 - 338

17
C₁₉H₂₂N₂O₄ [ No CAS ]
[ 1361224-53-4 ]