[ CAS No. 886766-28-5 ] {[proInfo.proName]}

Name: 886766-28-5|tert-Butyl 4,7-diazaspiro[2.5]octane-7-carboxylate|95%
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SKU: A130297
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Quality Control of [ 886766-28-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 886766-28-5 ]

Product Details of [ 886766-28-5 ]

CAS No. :	886766-28-5	MDL No. :	MFCD08685931
Formula :	C₁₁H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XXKCYKIJWLFVDG-UHFFFAOYSA-N
M.W :	212.29	Pubchem ID :	46942212
Synonyms :

Calculated chemistry of [ 886766-28-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	66.04
TPSA :	41.57 Å²

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) :	-7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.79
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	0.53
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	1.05
Consensus Log Po/w :	1.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.48
Solubility :	7.01 mg/ml ; 0.033 mol/l
Class :	Very soluble
Log S (Ali) :	-1.29
Solubility :	11.0 mg/ml ; 0.0518 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.82
Solubility :	3.19 mg/ml ; 0.015 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.74

Safety of [ 886766-28-5 ]

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 [ 886766-28-5 ]

* 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 [ 886766-28-5 ]

[ 886766-28-5 ] Synthesis Path-Downstream 1~11

1
[ 591-50-4 ]
[ 886766-28-5 ]
[ 1254981-66-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	With cesium hydroxide; In dimethyl sulfoxide; at 120℃; for 0.666667h;Sealed tube;	A stirred solution of <strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong> (0.1 g, 0.471 mmol) [C.A.S. 886766-28-5] , iodobenzene (0.026 ml, 0.236) and CsOH (0.079 g, 0.471 mmol) in DMSO (1 ml) was heated in a sealed tube at 1200C for 20 min. After cooling, additional <strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong> (2 eq.) was added, and the mixture was then heated at 1200C for 20 min. The mixture was cooled.The mixture was washed with NH4Cl (aqueous sat. solution) was added and extracted with Et2O. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by manifold (Sep-Pak.(R). silica cartridge; DCM as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D61 (0.021 g, 31percent) as a white solid.

Reference： [1]Patent: WO2010/130424,2010,A1 .Location in patent: Page/Page column 121-122

3
[ 886766-28-5 ]
[ 1200114-08-4 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2:4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane hydrochloridePyridine (500 mul) and trifluoroacetic anhydride (786 mul, 5.64 mmol) were added to a dichloromethane (10 ml) solution of the compound (1.0 g, 4.70 mmol) obtained in Step 1 above under ice cooling and the resulting mixture was stirred for 15 minutes.After completion of the reaction, trifluoroacetic acid (6 ml) was added and the resulting mixture was stirred at room temperature for 1 hour.The reaction solvent was evaporated under reduced pressure and then the residue was subjected to azeotropic distillation with toluene.The residue was diluted with chloroform and the organic layer was washed with saturated aqueous sodium bicarbonate solution and brine and dried over anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [chloroform:methanol = 40:1 (v/v)].The residue obtained was subjected to azeotropic distillation with 4 N hydrochloric acid/dioxane and then dried under reduced pressure to give the title compound (751 mg, 65percent) as a colorless solid.1H-NMR (400 MHz, DMSO-d6) delta: 1.15-1.21 (4H, m), 3.14-3.19 (2H, m), 3.24 (2H, t, J=5.4 Hz), 3.84-3.91 (2H, m).MS (ESI) m/z: 209 [(M+H)+].

Reference： [1]Patent: EP2298778,2011,A1 .Location in patent: Page/Page column 98

4
[ 886766-28-5 ]
[ 1403676-74-3 ]
tert-butyl 4-((1s,4s)-4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexyl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]
tert-butyl 4-((1r,4r)-4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexyl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.4%; 2.3%		To a solution of tert-b tyl 4,7-diazaspiro[2.5]octane-7-carboxylate (0.16 g, 0.73 mmol) and 4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexanone (0.20 g, 0.67 mmol) in DCE (5 mL) at room temperature under nitrogen was added acetic acid (76.0 mu, 1.30 mmol) and sodium triacetoxyborohydride (0.35 g, 1.7 mmol). The mixture was heated at 45 °C for 3 days. The reaction formed a major side product (alcohol) from ketone starting material. The mixture was quenched with saturated NaHC03 (aq.). The organic layer was separated and the aqueous layer was extracted once with DCM. The combined organic phases were concentrated under reduced pressure and purified by preparative HPLC. The pure fractions were combined, neutralized with saturated NaHC03 (aq.), and concentrated under reduced pressure. The aqueous residue was extracted twice with DCM and the combined organic layers were dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the more polar title compound as an off-white gum (7.7 mg, 2.3percent). The less polar cis analog was also obtained as an off-white gum (1.2 mg, 0.4percent). Exact mass calculated for C25H37FN2O5S: 496.2, found: LCMS m/z = 497.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 0.55-0.64 (m, 2H), 0.66-0.72 (m, 2H), 1.08-1.36 (m, 4H), 1.45 (s, 9H), 1.75-1.89 (m, 1H), 1.93-2.02 (m, 2H), 2.09-2.18 (m, 2H), 2.87-2.97 (m, 1H), 3.03 (s, 3H), 3.08-3.13 (m, 2H), 3.17 (s, 2H), 3.40 (bs, 2H), 3.90 (d, J = 6.32 Hz, 2H), 7.06 (t, J = 8.21 Hz, 1H), 7.62-7.66 (m, 1H), 7.66-7.70 (m, 1H).

Reference： [1]Patent: WO2012/145361,2012,A1 .Location in patent: Page/Page column 201

5
[ 886766-28-5 ]
3-methyl-1-(tetrahydropyran-2-yl)-6-[4-(tetrahydropyran-2-yloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid sodium salt [ No CAS ]
4-{3-methyl-1-(tetrahydropyran-2-yl)-6-[4-(tetrahydropyran-2-yloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carbonyl}-4,7-diazaspiro[2.5]octane-7-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a suspension of 300 mg of 3-methyl-1 -(tetrahydro-pyran-2-yl)-6-[4-(tetrahydro- pyran-2-yloxy)-phenyl]-1 H-pyrazolo[3,4-b]pyridine-4-carboxylic acid sodium salt in 7.5 ml of DCM were added 0.12 ml of Hunig's base, 376 mg of BEP and 146 mg of<strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong>. The reaction was stirred overnight at r.t.. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 280 mg (66%) of the title compound. LC/MS (Method LC4): Rt = 1 .24 min; m/z = 632.20 [M+H]+.

Reference： [1]Patent: WO2013/167403,2013,A1 .Location in patent: Page/Page column 218; 219

6
[ 886766-28-5 ]
[ 823-62-1 ]
tert-butyl 4-(5-amino-6-chloro-1,2,4-triazin-3-yl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 155℃; for 9.5h;Microwave irradiation;	A vial was charged with 5-amino-3,6-dichloro-l,2,4-triazine (108.5 mg, 0.658 mmol), diisopropylethylamine (0.5 mL, 2.87 mmol), tert-butyl 2-(4,7-diazaspiro[2.5]octan-7- yl)acetate (154.8 mg, 0.650 mmol) in dioxane (2.5 mL). The mixture was heated at 155 C for 9.5 h using microwave. The mixture was concentrated to remove all of solvent. The residue was dissolved in dichloromethane, washed with aqueous sodium bicarbonate solution. The organic solution was separated. The aqueous solution was mixed with brine, extracted with dichloromethane (2 x 35 mL). The combined organic solution was dried over anhydrous sulfate, concentrated to afford a residue. The residue was purified with flash column chromatography on silica using 1-10% methanol in dichloromethane to afford product (118.3 mg) in 53% yield. NMR (500 MHz, Chloroform-d) delta 5.24 (s, 2H), 3.91 (t, J = 4.5 Hz, 2H), 3.42 (m, 2H), 3.33 (s, 2H), 1.43 (s, 9H), 0.96 (m, 4H). MS for C14H21 CIN6O2: 341.2 (MH+).

Reference： [1]Patent: WO2015/92819,2015,A2 .Location in patent: Paragraph 0715; 0716

7
[ 886766-28-5 ]
[ 98-88-4 ]
C₁₈H₂₄N₂O₃ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 10218 - 10225

8
[ 886766-28-5 ]
[ 98-88-4 ]
tert-butyl 4-benzoyl-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 10218 - 10225

9
[ 39079-62-4 ]
[ 886766-28-5 ]
(E)-tert-butyl 4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4800 - 4811

10
ethyl 2-((1-(((tert-butoxy)carbonyl)amino)cyclopropyl)carbonylamino)acetate [ No CAS ]
[ 886766-28-5 ]

Reference： [1]Patent: CN105111155,2018,B

11
[ 24424-99-5 ]
4,7-diazaspiro[2.5]octane [ No CAS ]
[ 886766-28-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydroxide; In ethanol; at 5 - 30℃; for 13h;	In the 1L three-mouth reaction bottle,64.9 g of 4,7-diazaspiro[2.5]octane and 650 mL of EtOH were added in sequence.Temperature control below 30 °C,Slowly add 51g NaOH,Temperature control below 5 °C,Add 252.6g (Boc) 2O dropwise,After the addition is completed, slowly rise to room temperature. Stir the reaction at room temperature for 13 h,TLC monitors the reaction completely,filter,Desolvent,Purified by the column49.7-diazaspiro[2.5]octane-7-carboxylic acid tert-butyl ester 89.7 g,The yield was 73percent.

Reference： [1]Patent: CN105111155,2018,B .Location in patent: Paragraph 0050; 0051; 0067; 0068

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 886766-28-5 ] {[proInfo.proName]}

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[ 886766-28-5 ] Synthesis Path-Downstream 1~11

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Aliphatic Heterocycles

Piperazines

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[ 886766-28-5 ]

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