[ CAS No. 885270-84-8 ] {[proInfo.proName]}

Name: 885270-84-8|tert-Butyl 2,6-diazaspiro[3.4]octane-2-carboxylate|97%
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SKU: A216997
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Quality Control of [ 885270-84-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 885270-84-8 ]

CAS No. :	885270-84-8	MDL No. :	MFCD08234737
Formula :	C₁₁H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJIOQJJFPYXAEM-UHFFFAOYSA-N
M.W :	212.29	Pubchem ID :	49757941
Synonyms :

Calculated chemistry of [ 885270-84-8 ]

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 :	65.74
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) :	-7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.71
Log Po/w (XLOGP3) :	0.7
Log Po/w (WLOGP) :	0.46
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	1.05
Consensus Log Po/w :	1.21

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.4
Solubility :	8.47 mg/ml ; 0.0399 mol/l
Class :	Very soluble
Log S (Ali) :	-1.15
Solubility :	15.0 mg/ml ; 0.0707 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 :	2.71

Safety of [ 885270-84-8 ]

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 [ 885270-84-8 ]

* 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 [ 885270-84-8 ]

[ 885270-84-8 ] Synthesis Path-Downstream 1~87

1
[ 1336911-04-6 ]
[ 885270-84-8 ]
[ 1392889-12-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5326 - 5329

2
[ 1336911-04-6 ]
[ 885270-84-8 ]
C₂₈H₃₆N₈O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5326 - 5329

3
[ 885270-84-8 ]
trans-2-(pyridin-4-yl)cyclopropanecarboxylic acid [ No CAS ]
[ 1541194-32-4 ]
[ 1541194-35-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792

4
[ 885270-84-8 ]
1-(2,6-diazaspiro[3.4]octan-6-yl)prop-2-en-1-one hydrochloride [ No CAS ]

Reference： [1]Patent: US2014/288045,2014,A1

5
[ 885270-84-8 ]
1-(2-((4,5-dichloro-2-hydroxyphenyl)glycyl)-2,6-diazaspiro[3.4]octan-6-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Patent: US2014/288045,2014,A1
[2]Patent: WO2016/44772,2016,A1

6
[ 885270-84-8 ]
[ 814-68-6 ]
2,6-diazaspiro[3.4]octane-6-acryloyl-2-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; In dichloromethane; at 20℃; for 1h;	Example 10 2,6-Diaza-spiro[3.4]octane-6-acryloyl-2-carboxylic acid tert-butyl ester To a mixture of 2,6-diaza-spiro[3.4]octane-2-carboxylic acid tert-butyl ester (80 mg, 0.38 mmol), Et3N (0.2 mL, 1.44 mmol) in DCM (20 mL), acryloyl chloride (34 mg, 0.38 mmol) was added and the resulting mixture was stirred at room temperature for 1 h. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (DCM/MeOH=40:1) to afford the desired product (50 mg, 50% yield). ESI-MS m/z: 289.2[M+Na]+.
50%	With triethylamine; In dichloromethane; at 20℃; for 1h;	To a mixture of <strong>[885270-84-8]2,6-diaza-spiro [3 .4]octane-2-carboxylic acid tert-butyl ester</strong> (80 mg, 0.38 mmol), Et3N (0.2 mL, 1.44 mmol) in DCM (20 mL), acryloylchloride (34 mg, 0.38 mmol) was added and the resulting mixture was stirred at room temperature for 1 h. The mixture was poured into water and extracted with ethylacetate. The organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2504 and concentrated in vacuo. The residue was purified by flash columnchromatography on silica gel (DCM/MeOH = 40:1) to afford the desired product (50mg, 50% yield). ESI-MS m/z: 289.2 [M+Na]b.

Reference： [1]Patent: US2014/288045,2014,A1 .Location in patent: Paragraph 0496
[2]Patent: WO2016/44772,2016,A1 .Location in patent: Paragraph 302

7
[ 885270-84-8 ]
N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-formamide [ No CAS ]
C₃₁H₃₇ClN₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 4h;	In absolute anhydrous THF (10 mL) were dissolved N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2 -(methylsulfinyl)pyrimidine-5-formamide (170 mg, 0.38 mmol) and <strong>[885270-84-8]tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate</strong> (74 mg, 0.35 mmol). Triethylamine (101 mg, 1.0 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 4 h, followed by addition of water and extraction with DCM. The organic phase was dried over sodium sulfate and concentrated. The obtained solid was purified by silica gel column chromatography (DCM / methanol = 80/1) to give a white solid (100 mg). The product was dissolved in DCM (15 mL), and trifluoroacetic acid (1 mL) was added. The reaction mixture was stirred at ambient temperature for 2 h. The solvent was removed to give N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(2,6-diazaspiro[3.4] octan-6-yl)pyrimidine-5-formamide (38 mg, 20 % total yield). Molecular formula: C26H29ClN6O2 Molecular weight: 493.0 MS (m/e): 493.0 (M+H+) 1H-NMR (400 MHz, DMSO-d6, trifluoroacetate salt): delta ?9.90 (brs, 1H), 9.18 (m, 3H), 8.41 (s, 1H), 7.24-7.48 (m, 7H), 7.10 (m, 1H), 4.58 (m, 2H), 4.22 (d, 2H), 4.04 (m, 2H), 3.94 (m, 2H), 3.83 (d, 2H), 3.81 (s, 3H), 3.74 (m, 2H), 3.56 (m, 2H), 2.27 (m, 2H).

Reference： [1]Patent: EP2886540,2015,A1 .Location in patent: Paragraph 0261

8
[ 885270-84-8 ]
[ 79-22-1 ]
2-tert-butyl 6-methyl-2,6-diaza-spiro[3.4]octane-2,6-di-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	[00403] Step 1: Synthesis of 2-tert-butyl 6-methyl 2,6-diazaspiro[3.4]octane-2,6-di- Carboxylate. To a solution of <strong>[885270-84-8]tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate</strong> (100 mg, 0.47 mmol) in DCM (2 mL) stirred at 0oC was treated with Et3N (95 mg, 0.94 mmol) followed by slow addition of methyl chloroformate (89 mg, 0.94 mmol), and the reaction mixture further stirred at room temperature for 16 h., diluted with EtOAc (20 mL) and consecutively washed with H2O (20 mL), aqueous NH4Cl solution (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give 2-tert-butyl 6-methyl 2,6-diazaspiro[3.4]octane-2,6-dicarboxylate (100 mg, 78% yield) as a yellow solid. ESI-LCMS (m/z): 293.1 [M+Na]+.

Reference： [1]Patent: WO2016/44641,2016,A2 .Location in patent: Paragraph 00403

9
[ 885270-84-8 ]
methyl 2,6-diazaspiro[3.4]octane-6-carboxylate TFA salt [ No CAS ]

Reference： [1]Patent: WO2016/44641,2016,A2

10
[ 885270-84-8 ]
methyl 2-(2-(5-((R)-3-(tert-butoxycarbonyl(methyl)amino)-2-(tert-butyldimethylsilyloxy)propoxy)-2-chlorophenyl)-6-(3,5-dimethylisoxazol-4-yl)-5-methylpyrimidin-4-yl)-2,6-diazaspiro[3.4]octane-6-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/44641,2016,A2

11
[ 885270-84-8 ]
methyl 2-(2-(2-chloro-5-((R)-2-hydroxy-3-(methylamino)propoxy)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-5-methylpyrimidin-4-yl)-2,6-diaza-spiro[3.4]octane-6-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/44641,2016,A2

12
[ 885270-84-8 ]
1-(2,6-diazaspiro[3.4]octan-6-yl)prop-2-en-1-one hydrochloride [ No CAS ]

Reference： [1]Patent: WO2016/44772,2016,A1

13
[ 885270-84-8 ]
(6-(5-chlorobenzo[d]oxazol-2-yl)-2,6-diazaspiro[3.4]octan-2-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 2132 - 2146

14
[ 885270-84-8 ]
C₁₃H₁₄ClN₃O*ClH [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 2132 - 2146

15
[ 885270-84-8 ]
(2-(5-chlorobenzo[d]oxazol-2-yl)-2,6-diazaspiro[3.4]octan-6-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 2132 - 2146

16
[ 885270-84-8 ]
C₁₆H₁₉N₅O*ClH [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 2132 - 2146

17
[ 956317-36-5 ]
[ 885270-84-8 ]
C₂₁H₂₇N₅O₃ [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 2132 - 2146

18
[ 3621-81-6 ]
[ 885270-84-8 ]
C₁₈H₂₂ClN₃O₃ [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 2132 - 2146

19
[ 95-49-8 ]
[ 885270-84-8 ]
C₁₈H₂₆N₂O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 466 - 469

20
[ 623-12-1 ]
[ 885270-84-8 ]
C₁₈H₂₆N₂O₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 466 - 469

21
[ 352-33-0 ]
[ 885270-84-8 ]
C₁₇H₂₃FN₂O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 466 - 469

22
[ 885270-84-8 ]
[ 89763-93-9 ]
tert-butyl 6-(2-formyl-5-(trifluoromethyl)phenyl)-2,6-diazaspiro[3.4]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In dimethyl sulfoxide; at 80℃;Inert atmosphere;	A 100-mL round-bottom flask was charged with 2-fluoro-4- (trifluoromethyl)benzaldehyde (1.00 g, 5.21 mmol, 1.00 equiv), DMSO (20 mL), tert-butyl 2,6- diazaspiro[3.4]octane-2-carboxylate (1.66 g, 7.82 mmol, 1.50 equiv), and potassium carbonate (2.16 g, 15.6 mmol, 3.00 equiv) under nitrogen. The resulting solution was stirred overnight at 80 C and quenched with water (20 mL). The resulting solution was extracted with EtOAc (3 x20 mL) and the organic layers were combined, washed with brine (2 x 20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 1.40 g (70% yield) of tert-butyl 6-(2-formyl- 5 -(trifluoromethyl)phenyl)-2,6-diazaspiro[3 .4] octane-2-carboxylate as a yellow oil. LCMS (ESI, m/z): 385 [M+Hfb.

Reference： [1]Patent: WO2017/87854,2017,A1 .Location in patent: Paragraph 00201

23
[ 885270-84-8 ]
2-(2,6-diazaspiro[3.4]octan-6-yl)-4-(trifluoromethyl)benzaldehyde [ No CAS ]

Reference： [1]Patent: WO2017/87854,2017,A1

24
[ 885270-84-8 ]
2-(2-(methylsulfonyl)-2,6-diazaspiro[3.4]octan-6-yl)-4-(trifluoromethyl)benzaldehyde [ No CAS ]

Reference： [1]Patent: WO2017/87854,2017,A1

25
[ 885270-84-8 ]
C₁₀H₁₀N₂O₄ [ No CAS ]
C₁₆H₂₀N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2017/197036,2017,A1 .Location in patent: Page/Page column 346

26
[ 885270-84-8 ]
C₁₀H₁₀N₂O₄ [ No CAS ]
C₅₂H₅₉ClFN₉O₁₂S [ No CAS ]

Reference： [1]Patent: WO2017/197036,2017,A1

27
[ 885270-84-8 ]
3-bromo-5-fluoro-9H-xanthen-9-one [ No CAS ]
tert-butyl 7-(5-fluoro-9-oxo-xanthen-3-yl)-2,7-diazaspiro[3.4]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34.5%	With potassium phosphate; In 1-methyl-pyrrolidin-2-one; at 25 - 90℃; for 16h;	To a mixture of 3-bromo-5-fluoro-xanthen-9-one (0.1 g, 0.341 mmol) in NMP (2 mL) was added <strong>[885270-84-8]tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate</strong> (86.9 mg, 0.341 mmol, vendor: PharmaBlock (Nanjing) R&D Co. Ltd, CAS : 885270-84-8, Cat.: as PB00717) and K3P04 (0.145 g, 0.682 mmol) at 25C. Then the mixture was stirred at 90C for 16 hours. The resulting mixture was poured into water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (elution with PE: EtOAc= 20: 1 to 1: 1) to give tert-butyl 7-(5-fluoro-9-oxo-xanthen-3-yl)-2,7- diazaspiro[3.4]octane-2-carboxylate (50.0 mg, 34.5%), MS obsd. (ESI+) [(M+H)+]: 425.1.

Reference： [1]Patent: WO2017/202798,2017,A1 .Location in patent: Page/Page column 66-67

28
[ 885270-84-8 ]
4-chloro-6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine [ No CAS ]
tert-butyl 6-[6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl]-2,6-diazaspiro[3.4]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-ethyl-N,N-diisopropylamine; In ethanol; at 20℃; for 18h;	To a mixture of 4-chloro-6- (2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine (3.00 g, 11.9mmol) and tert-butyl 2,6-diazaspiro[3.4] octane-2-carboxylate (2.5 g, 11.8 mmol) inEtOH (50 mL) was added DIPEA (2 g, 15.5 mmol) in one portion. The mixture was stirred at room temperature for 18 h. The mixture was evaporated and the residue was diluted in EA (200 mL). The solution was washed with water (100 mL*2), dried over Na2SO4, filtered and evaporated to give intermediate 3 (5.10 g, 11.9 mmol, 100% yield)as brown oil.

Reference： [1]Patent: WO2018/50686,2018,A1 .Location in patent: Page/Page column 65; 66
[2]Patent: WO2017/207387,2017,A1 .Location in patent: Page/Page column 102

29
[ 885270-84-8 ]
[ 18520-07-5 ]
tert-butyl-6-(6-chloro-3,5-dicyano-4-ethylpyridin-2-yl)-2,6-diazaspiro[3.4]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In dichloromethane; for 0.5h;	To a solution of 2,6-dichloro-4-ethylpyridine-3,5-dicarbonitrile (synthesis described in example 3 step 2, 900 mg, 4 mmol) and <strong>[885270-84-8]tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate</strong> (840 mg, 4 mmol) in dichloromethane (100 mL) was added triethylamine (400 mg, 4 mmol). The reaction was stirred for 30 minutes, was then washed with brine (2 x 100 mL), and the organic phase was dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether- ethyl acetate (3:1) to give the title compound (1.3 g, 81% yield). LCMS m/z = 346 [M+H-isobutylene]+.

Reference： [1]Patent: WO2017/216726,2017,A1 .Location in patent: Page/Page column 596

30
[ 885270-84-8 ]
C₁₃H₁₈N₂O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9905 - 9910

31
[ 885270-84-8 ]
6-(2-methoxyphenyl)-2-(3-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)thio)propyl)-2,6-diazaspiro[3.4]octane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9905 - 9910

32
[ 885270-84-8 ]
1-halide-2-methoxybenzene [ No CAS ]
C₁₈H₂₆N₂O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9905 - 9910

33
[ 885270-84-8 ]
C₂₅H₃₄F₃N₅O₂S [ No CAS ]