[ CAS No. 937174-76-0 ] {[proInfo.proName]}

Name: 937174-76-0|(S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol|98+%
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SKU: A111141
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Quality Control of [ 937174-76-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 937174-76-0 ]

SDS Specification

Alternatived Products of [ 937174-76-0 ]

Product Details of [ 937174-76-0 ]

CAS No. :	937174-76-0	MDL No. :	MFCD14105605
Formula :	C₂₁H₂₇N₇O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KGPGFQWBCSZGEL-ZDUSSCGKSA-N
M.W :	425.48	Pubchem ID :	16725726
Synonyms :		Chemical Name :	(S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol

Calculated chemistry of [ 937174-76-0 ]

Physicochemical Properties

Num. heavy atoms :	31
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.52
Num. rotatable bonds :	5
Num. H-bond acceptors :	8.0
Num. H-bond donors :	3.0
Molar Refractivity :	119.98
TPSA :	137.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.7
Log Po/w (XLOGP3) :	0.27
Log Po/w (WLOGP) :	1.29
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	1.73
Consensus Log Po/w :	1.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.65
Solubility :	0.948 mg/ml ; 0.00223 mol/l
Class :	Soluble
Log S (Ali) :	-2.71
Solubility :	0.827 mg/ml ; 0.00194 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.72
Solubility :	0.00816 mg/ml ; 0.0000192 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.57

Safety of [ 937174-76-0 ]

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 [ 937174-76-0 ]

* 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 [ 937174-76-0 ]
Downstream synthetic route of [ 937174-76-0 ]

[ 937174-76-0 ] Synthesis Path-Upstream 1~9

1
[ 937174-75-9 ]
[ 937174-76-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 2.5 h; Stage #2: With sodium hydroxide In tetrahydrofuran; dichloromethane; water; ethyl acetate	The compound of Example 1 (c) (35.0 g, 66.6 mmol) and TFA (350 ml. of a 20percent solution in methylene chloride, 808 mmol) was stirred at ambient temperature for 2.5 h. The solution was poured slowly into rapidly stirring mixture of water, NaOH (36 g, 900 mmol), ethyl acetate (200 ml.) and THF (1000 ml_). The organic layer was separated and the aqueous layer was extracted with additional ethyl acetate/THF (1 :5 v/v, 150 ml_). The combined organic extract were washed with sat. NaCI, dried over Na₂SO₄. The solvent was removed under vacuum and the resulting solid was recrystallized from hot ethanol (1200 ml.) to give 26.3 g (93percent yield) of the title compound as a white crystalline solid. MS (ES+) m/z 426 (M+H)⁺.

Reference： [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5663 - 5679
[2] Patent: WO2008/121685, 2008, A1, . Location in patent: Page/Page column 39

2
[ 607371-01-7 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

3
[ 842144-03-0 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

4
[ 842144-05-2 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

5
[ 842144-04-1 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

6
[ 842149-46-6 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

7
[ 158406-99-6 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

8
[ 937174-74-8 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

9
[ 140695-84-7 ]
[ 937174-76-0 ]

Reference： [1] Patent: WO2008/121685, 2008, A1,

[ 937174-76-0 ] Synthesis Path-Downstream 1~12

1
[ 937174-75-9 ]
[ 937174-76-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With trifluoroacetic acid In dichloromethane at 20℃; for 2.5h; Inert atmosphere;
93%	Stage #1: 1,1-dimethylethyl (3S)-3-([2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-1-piperidinecarboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 2.5h; Stage #2: With sodium hydroxide In tetrahydrofuran; dichloromethane; water; ethyl acetate	1.d The compound of Example 1 (c) (35.0 g, 66.6 mmol) and TFA (350 ml. of a 20% solution in methylene chloride, 808 mmol) was stirred at ambient temperature for 2.5 h. The solution was poured slowly into rapidly stirring mixture of water, NaOH (36 g, 900 mmol), ethyl acetate (200 ml.) and THF (1000 ml_). The organic layer was separated and the aqueous layer was extracted with additional ethyl acetate/THF (1 :5 v/v, 150 ml_). The combined organic extract were washed with sat. NaCI, dried over Na2SO4. The solvent was removed under vacuum and the resulting solid was recrystallized from hot ethanol (1200 ml.) to give 26.3 g (93% yield) of the title compound as a white crystalline solid. MS (ES+) m/z 426 (M+H)+.

Reference： [1]Location in patent: experimental part Heerding, Dirk A.; Rhodes, Nelson; Leber, Jack D.; Clark, Tammy J.; Keenan, Richard M.; Lafrance, Louis V.; Li, Mei; Safonov, Igor G.; Takata, Dennis T.; Venslavsky, Joseph W.; Yamashita, Dennis S.; Choudhry, Anthony E.; Copeland, Robert A.; Lai, Zhihong; Schaber, Michael D.; Tummino, Peter J.; Strum, Susan L.; Wood, Edgar R.; Duckett, Derek R.; Eberwein, Derek; Knick, Victoria B.; Lansing, Timothy J.; McConnell, Randy T.; Zhang, ShuYun; Minthorn, Elisabeth A.; Concha, Nestor O.; Warren, Gregory L.; Kumar, Rakesh [Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5663 - 5679]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/121685, 2008, A1 Location in patent: Page/Page column 39

2
[ 607371-01-7 ]
[ 937174-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: hydrogenchloride; water; tin(ll) chloride / 85 °C / Heating / reflux 1.2: 0 °C / pH 12 2.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C 3.1: acetic acid / 3 h / 100 °C 4.1: sodium nitrate / 16 h / 20 °C 5.1: hydroxylamine hydrochloride; triethylamine / 1,4-dioxane; water / 6 h / Heating / reflux 6.1: methanol / 0.5 h / 65 °C 7.1: isopropyl magnesium chloride / tetrahydrofuran; diethyl ether / 0.17 h / -75 - -70 °C / Cooling with acetone-dry ice 7.2: 19 h / 20 °C / Cooling with acetone-dry ice 8.1: caesium carbonate / N,N-dimethyl-formamide / 26 h / 35 - 40 °C 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dimethyl sulfoxide / 4.17 h / 80 °C 10.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C