[ CAS No. 1023595-19-8 ] {[proInfo.proName]}

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Quality Control of [ 1023595-19-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1023595-19-8 ]

SDS Specification

Alternatived Products of [ 1023595-19-8 ]

Product Details of [ 1023595-19-8 ]

CAS No. :	1023595-19-8	MDL No. :	MFCD10700117
Formula :	C₁₄H₂₆N₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QDWTYWWOUAIWGI-UHFFFAOYSA-N
M.W :	254.37	Pubchem ID :	46912008
Synonyms :

Calculated chemistry of [ 1023595-19-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.93
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	80.16
TPSA :	41.57 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.16
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	1.97
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	1.18 mg/ml ; 0.00463 mol/l
Class :	Soluble
Log S (Ali) :	-2.26
Solubility :	1.39 mg/ml ; 0.00548 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.66
Solubility :	0.559 mg/ml ; 0.0022 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.9

Safety of [ 1023595-19-8 ]

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

Application In Synthesis of [ 1023595-19-8 ]

* 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.

Downstream synthetic route of [ 1023595-19-8 ]

[ 1023595-19-8 ] Synthesis Path-Downstream 1~15

1
[ 1023595-19-8 ]
[ 7379-35-3 ]
[ 1246507-83-4 ]

Yield	Reaction Conditions	Operation in experiment
51.4%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 15h;Reflux;	Step (i): tert-Butyl 2-(pyridin-4-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate tert-Butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate (1 g, 3.931 mmol), 4-chloropyridinium chloride (1.765 g, 11.794 mmol) and N-ethyl-diisopropylamine (2.7 ml, 15.724 mmol) were refluxed in 2-propanol (8 ml) for 15 h, saturated NaHCO3 solution (20 ml) and ethyl acetate (8 ml) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2*80 ml). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica; ethyl acetate/methanol/ammonia (25 aq.) 100:10:0.25). Yield: 0.67 g (51.4%)

Reference： [1]Patent: US2010/249095,2010,A1 .Location in patent: Page/Page column 121

2
[ 1023595-19-8 ]
[ 1246506-61-5 ]
[ 1246508-28-0 ]

Yield	Reaction Conditions	Operation in experiment
70%		Step 1: (R)-tert-Butyl 2-(3-(2-chlorobenzamido)-2,3-dihydro-1H-indene-5-carbonyl)-2,9-diazaspiro[5.5]undecane-9-carboxylate N-Ethyl-diisopropylamine (4 eq.) was added to a solution of (3R)-3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid (E-03) (0.952 mmol, 1 eq.) in methylene chloride (18 ml). The reaction mixture was cooled to 0 C. and N-ethyl-N'-3-(dimethylamino)-propyl-carbodiimide hydrochloride (1.2 eq.) and 1-hydroxybenzotriazole hydrate (0.2 eq.) were then added. The mixture was stirred at this temperature for 15 min, before <strong>[1023595-19-8]tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate</strong> (1.1 eq.) was added. The reaction mixture was stirred at room temperature for 2.5 d. Then, the reaction mixture was washed in each case 1* with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica; ethyl acetate/hexane/ammonia (25 aq.) 70:10:0.8). Yield: 70%

Reference： [1]Patent: US2010/249095,2010,A1 .Location in patent: Page/Page column 174-175

3
[ 1023595-19-8 ]
[ 1313733-33-3 ]
[ 1313802-12-8 ]
[ 1313802-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: <strong>[1023595-19-8]2,9-diaza-spiro[5.5]undecane-9-carboxylic acid tert-butyl ester</strong>HPLC-MS (method 1 ): Rt = 3.44 min, [M+H]+ m/z 504.3.1H NMR (300 MHz, MeOD) S 8.40 (m, 2H), 7.71 (m, 1 H), 7.50 (d, J = 7.8 Hz, 1 H), 4.46 (m, 2H), 3.70 (m, 2H), 3.54 (m, 2H), 3.41 (m, 2H), 3.15 (m, 4H), 3.02 (s, 3H), 1.82 (m, 8H).Example 685-(2,9-Diaza-spiro[5.5]undec-2-yl)-6-methyl-3-(3-trifluoromethoxy-phenyl)- 7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta[a]naphthalene; HCI saltAmine: <strong>[1023595-19-8]2,9-diaza-spiro[5.5]undecane-9-carboxylic acid tert-butyl ester</strong>HPLC-MS (method 1): Rt = 4.50 min, [M+H)+ m/z 504.3.1H NMR (300 MHz, MeOD) delta 8.52 (s, 1 H), 8.38 (d, J = 7.5 Hz, 1 H), 7.74 (m, 1 H), 7.54 (d, J = 8.3 Hz, 1 H), 4.49 (m, 2H), 3.54 (m, 2H), 3.43 (m, 4H), 3.21 (m, 4H), 3.02 (s, 3H), 1.83 (m, 8H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 118

4
[ 1023595-19-8 ]
[ 1276676-86-8 ]
[ 1276676-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; N,N-dimethyl acetamide;bis(tri-t-butylphosphine)palladium(0); at 100℃; for 18h;	Anhydrous dimethylacetamide (95 mu, degassed prior to use) was added to a mixture of 5-chloro-l-(2,2-dimethylpropyl)-3-methyl-l,3-dihydro-2H-imidazo[4,5-?]pyridin-2- one (1-4, 20 mg, 0.079 mmol), potassium phosphate tribasic (33.5 mg, 0.158 mmol), bis(tri-t- butylphosphine)palladium(O) (1.61 mg, 3.15 muiotaetaomicron), and tert-butyl 2,9-diazaspiro-[5.5]undecane- 9-carboxylate (30.1 mg, 0.118 mmol). The resulting suspension was heated to 100 C for 18 h. Following this duration, the reaction contents were cooled to room temperature, filtered, and washed with acetonitrile . Purification using reverse-phase chromatography (10-100%, 0.1% TFA in F￡20: acetonitrile) affordedJert-butyl 2-[l-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3- dihydro-lH-imidazo[4,5-?]pyridin-5-yl]-2,9-diazaspiro[5.5]undecane-9-carboxylate (22-1) as a white solid. MS m/z (Mu+Eta): calculated = 472.3282; observed = 472.3275.

Reference： [1]Patent: WO2011/34741,2011,A1 .Location in patent: Page/Page column 105

5
[ 1023595-19-8 ]
[ 1417848-17-9 ]
[ 1417839-87-2 ]

Reference： [1]Patent: WO2013/4984,2013,A1

6
[ 1023595-19-8 ]
[ 1417848-17-9 ]
C₃₁H₃₇F₃N₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Exam le: Synthesis of final product 19A solution of Intermediate 1-46 (120 mg, 0.291 mmol) and 2,9-diaza- spiro[5.5]undecane-9-carboxylic acid fert-butyl ester (296 mg, 1.16 mmol) in DMA (10 ml.) was heated at 100 C for 48 h. Et3N (0.081 mL, 0.58 mmol) was added ad the reaction was heated at 100 C for 24 h. The solvent was removed in vacuo, water was added (20 mL) and the mixture was extracted with DCM. The combined organic layers were dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (Biotage, EtOAc:cHex 70:30). The product obtained was dissolved in MeOH (4 mL) and HCI 4M in dioxane (10 mL) was added. The reaction was stirred at rt for 4 h. The mixture was evaporated, and the residue was treated with 7N NH3 in MeOH. The residue was purified by column chromatography (Biotage, 7N NH3 in MeOH: DCM, 0:100 to 8:92) to afford Final Product 19 (100 mg, 65%) as a white solid.

Reference： [1]Patent: WO2013/4984,2013,A1 .Location in patent: Page/Page column 91

7
[ 1023595-19-8 ]
[ 87-42-3 ]
C₁₉H₂₈N₆O₂ [ No CAS ]