[ CAS No. 753440-87-8 ] {[proInfo.proName]}

Name: 753440-87-8|Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one|97%
Brand: Ambeed
SKU: A137230
Rating: 97 (29 reviews)

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2D 3D

Structure of 753440-87-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 753440-87-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 753440-87-8 ]

SDS Specification

Alternatived Products of [ 753440-87-8 ]

Product Details of [ 753440-87-8 ]

CAS No. :	753440-87-8	MDL No. :	MFCD13195370
Formula :	C₁₁H₁₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HNGKYJPFWVQZSF-UHFFFAOYSA-N
M.W :	219.24	Pubchem ID :	56763854
Synonyms :

Calculated chemistry of [ 753440-87-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	0
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	64.72
TPSA :	63.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	0.25
Log Po/w (WLOGP) :	0.16
Log Po/w (MLOGP) :	0.3
Log Po/w (SILICOS-IT) :	1.18
Consensus Log Po/w :	0.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.63
Solubility :	5.09 mg/ml ; 0.0232 mol/l
Class :	Very soluble
Log S (Ali) :	-1.14
Solubility :	15.9 mg/ml ; 0.0726 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.41
Solubility :	0.0845 mg/ml ; 0.000385 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.05

Safety of [ 753440-87-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 753440-87-8 ]

* 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 [ 753440-87-8 ]
Downstream synthetic route of [ 753440-87-8 ]

[ 753440-87-8 ] Synthesis Path-Upstream 1~1

1
[ 883984-95-0 ]
[ 753440-87-8 ]

Reference： [1] Patent: WO2007/16087, 2007, A2, . Location in patent: Page/Page column 49; 66
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6368 - 6372
[3] Patent: WO2006/41830, 2006, A2, . Location in patent: Page/Page column 55
[4] Patent: WO2006/44504, 2006, A1, . Location in patent: Page/Page column 80
[5] Patent: WO2006/99268, 2006, A2, . Location in patent: Page/Page column 66

[ 753440-87-8 ] Synthesis Path-Downstream 1~16

1
[ 883984-95-0 ]
[ 753440-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 24h;	10% Palladium on carbon (300 mg) was added to a solution of benzyl 7'-chloro-2'-oxo- r,2'-dihydro-lH-spiro[piperidme-4,4'-pyrido[2,3-(i][l,3]oxazine]-l-carboxylate (1.85 g, 1.77 mmol) in EtOH (250 mL). The reaction vessel was evacuated and back-filled with nitrogen (3x), then back-filled with hydrogen (1 atm). After 24 h, the mixture was filtered though celite and concentrated to give the title compound (1.07 g). MS: m/z = 220.1 (M + 1). lEta NMR (500 MHz, CD3OD) delta 8.26 (dd, J=1.7, 5.0 Hz, IH), 7.69 (dd, J=I.6, 7.7 Hz, IH), 7.16 (dd, J=5.0, 7.7 Hz, IH), 3.49-3.42 (m, 4H), 2.38-2.25 (m, 4H).
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 24h;	Step C. Spirorpiperidine-4.4'-pyridor2.3-c?\|'L31oxazin1-2'(rH)-one; 10% Palladium on carbon (300 mg) was added to a solution of benzyl 7'-chloro-2'-oxo- r,2'-dihydro-lH-spiro[piperidine-4,4'-pyrido[2,3-(f][l,3]oxazine]-l-carboxylate (1.85 g, 1.77 mmol) in EtOH (250 mL). The reaction vessel was evacuated and back-filled with nitrogen (3x), then back-filled with hydrogen (1 atm). After 24 h, the mixture was filtered though celite and concentrated to give the title compound (1.07 g). MS 220.1 (M + 1). lEta NMR (500 MHz, CD3OD) delta 8.26 (dd, J=I.7, 5.0 Hz,IH), 7.69 (dd, 3=1.6, 7.7 Hz, IH), 7.16 (dd, J=5.0, 7.7 Hz, IH), 3.49-3.42 (m, 4H), 2.38-2.25 (m, 4H).
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 28h;	Step C. Spirorpiperidine-4.4'-pyridor2.3-^ [1.31oxazinl-2'f 1 'ifl-one; Palladium (10% on carbon ;1.5 g) was added to a solution of benzyl 7'-chloro-2'- oxo- 1 ',2'-dibydro- 1 /f-spiro [piperidine-4,4l-pyrido [2,3 -d [ 1 ,3 ] oxazine] - 1 -carboxylate (3.01 g, 7.76 mmol) in ethanol (150 niL). The reaction vessel was evacuated and back-filled with nitrogen (3x), then back-filled with hydrogen (1 atm). After 24 h, additional palladium (10% on carbon; 0.5 g) was added. After 4 h, the mixture was filtered through celite and concentrated to give the title compound (1.62 g). MS 220.1 (M+l). lH NMR (500 MHz, CD3OD) delta 8.26 (dd, J= 1.7, 5.0 Hz, IH), 7.69 (dd, J= 1.6, 7.7 Hz, IH), 7.16 (dd, J= 5.0, 7.7 Hz, IH), 3.49-3.42 (m, 4H), 2.38-2.25 (m, 4H).

With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 24h;

10% Palladium on carbon (300 mg) was added to a solution of benzyl 7'-chloro-2'-oxo- r,2'-dihydro-lH-spiro[piperidine-4,4'-pyrido[2,3-T|[l,3]oxazine]-l-carboxylate (1.85 g, 1.77 mmol) in EtOH (250 mL). The reaction vessel was evacuated and back-filled with nitrogen (3x), then back-filled with hydrogen (1 atm). After 24 h, the mixture was filtered though celite and concentrated to give the title compound (1.07 g). MS 220.1 (M + 1). lEta NMR (500 MHz, CD3OD) delta 8.26 (dd, J=I.7, 5.0 Hz,IH), 7.69 (dd, J=I.6, 7.7 Hz, IH), 7.16 (dd, J=5.0, 7.7 Hz, IH), 3.49-3.42 (m, 4H), 2.38-2.25 (m, 4H).

Reference： [1]Patent: WO2007/16087,2007,A2 .Location in patent: Page/Page column 49; 66
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6368 - 6372
[3]Patent: WO2006/41830,2006,A2 .Location in patent: Page/Page column 55
[4]Patent: WO2006/44504,2006,A1 .Location in patent: Page/Page column 80
[5]Patent: WO2006/99268,2006,A2 .Location in patent: Page/Page column 66

2
[ 753440-87-8 ]
[ 7693-46-1 ]
[ 1354640-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; benzene; at 20℃;	4-Nitrophenyl 2'-oxo-1',2'-dihydrospiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazine]-1-carboxylate. In a 50 mL round-bottomed flask was <strong>[753440-87-8]spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one</strong> (187 mg, 0.853 mmol) (azeotroped with dry benzene) and 4-nitrophenyl carbonochloridate (174 mg, 0.861 mmol) in CH2Cl2 (6 mL) to give a tan solution. Et3N (0.238 mL, 1.706 mmol) was added, and the mixture was stirred at rt under nitrogen overnight (4:00 pm) and then over the weekend. The mixture still had some solids. 5 ml CHCl3 was added to dissolve the solids and the clear yellow solution was stirred for another day. TLC showed no starting amine. It was concentrated to dryness and further dried over high vacuum. The residue was then used as it is.

Reference： [1]Patent: US2009/258866,2009,A1 .Location in patent: Page/Page column 42

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[ 781650-41-7 ]
[ 753440-87-8 ]
[ 7693-46-1 ]
C₂₆H₂₆F₅N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 10; N-rr3i?.6S)-6-r2.3-difluorophenylV2-oxo-l-(2.2.2-trifluoroethvnazepan-3-yll-2-oxo-1.2-dihvdro-rH- spiro [3 , 1 -benzoxazine-4,4'-piperidine] - 1 '-carboxamide; Triethylamine (0.027 mL, 0.192 mmol) was added to a solution of (3i?,6S)-3-amino-6- (2,3-difluorophenyl)-l-(2,2,2-trifluoroethyl)azepan-2-one (62 mg, 0.192 mmol) and 4-nitrophenyl chloroformate (39 mg, 0.192 mmol) in tetrahydrofuran (3 mL) at 0 0C. After 60 min, spiro [piperidine- 4,4'-pyrido[2,3-^[l,3]oxazin]~2'(rH)-one (33 mg, 0.164 mmol), triethylamine (0.054 mL, 0.38 mmol), and chloroform (3 mL) were added and the mixture allowed to warm to ambient temperature. The reaction was stirred overnight, concentrated, diluted with saturated aqueous sodium bicarbonate and extracted with dichloromethane (2x). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane -> 91% dichloromethane/ methanol] gave the title compound (55 mg). MS 568.2023 (M+l). 1H NuMR (500 MHz, CDCl3) delta 8.26 (dd, J= 5.0 Hz, 1.5 Hz, IH), 7.95 (brs, IH), 7.43 (d, J= 7.3 Hz, IH), 7.08 (m, 3H), 6.95 (m, IH), 6.07 (d, J= 5.4 Hz, IH), 4.82 (dd, J= 10.6, 5.0 Hz, IH), 4.4 (m,lH), 4.0 (m, 4H), 3.45 (appq, 2H), 3.36 (d, J= 15.6 Hz, IH), 3.05 (dd, J= 10, 10 Hz, IH), 2.3-1.7 (m, 8H).

Reference： [1]Patent: WO2006/41830,2006,A2 .Location in patent: Page/Page column 77

4
[ 753440-87-8 ]
[ 880144-50-3 ]
[ 7693-46-1 ]
[ 885030-22-8 ]