191805-29-5|tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate| Ambeed

Structure of 191805-29-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 191805-29-5 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 191805-29-5 ]

CAS No. :	191805-29-5
Formula :	C₁₄H₂₃NO₃
M.W :	253.34
SMILES Code :	O=C(N(CC1)CCC21CCCC2=O)OC(C)(C)C
MDL No. :	MFCD18074085
InChI Key :	VFNVAGFIJXCMPA-UHFFFAOYSA-N
Pubchem ID :	10848487

Safety of [ 191805-29-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 191805-29-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	0
Fraction Csp3	0.86
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	73.65
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.61 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.88
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.38
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.86
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.2
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.19

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.23
Solubility	1.48 mg/ml ; 0.00584 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.21
Solubility	1.56 mg/ml ; 0.00615 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.5
Solubility	0.81 mg/ml ; 0.0032 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.7 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.82

Application In Synthesis of [ 191805-29-5 ]

* 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 [ 191805-29-5 ]

[ 191805-29-5 ] Synthesis Path-Downstream 1~35

1
[ 191805-27-3 ]
[ 191805-29-5 ]
tert-butyl 2-benzoyl-1-oxo-8-azaspiro[4.5]decane-8-carboxate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2374 - 2385.

2
[ 142851-03-4 ]
[ 191805-29-5 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2374 - 2385.
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 1781 - 1792.

3
[ 849203-09-4 ]
[ 191805-29-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; In tetrahydrofuran; ethanol; water; at 90℃; for 60h;	To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90 C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20-30% ethyl acetate in hexanes to give the title compound (9.41 g). 1H NMR (400 MHz, CDCl3): delta 1.29-1.37 (m, 2 H), 1.47 (s, 9 H), 1.62-1.69 (m, 2 H), 1.92-1.95 (m, 4 H), 2.30-2.34 (m, 2 H), 3.05-3.10 (m, 2 H), 3.87-3.92 (m, 2 H).
	With lithium hydroxide; In tetrahydrofuran; ethanol; water; at 90℃; for 60h;	Pulverized lithium hydroxide (26 g, 1.10 mol) was added to a solution of (&S)-8-(l,l-dimethylethyl) 2- methyl l-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate (Description 51, 17.2 g, 0.055 mol) in ethanol/THF/water (2:2:1, 555 mL) and the mixture was stirred at 90 0C for 60 h. The mixture was cooled and the solvent was evaporated under reduced pressure. Water was added and the mixture was EPO <DP n="30"/>extracted with CH2Cl2 (3x). The combined organic fractions were washed with brine, dried (Na2SO4), filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography, eluting with 20-30% EtOAc in hexanes, to give the title compound (9.41 g). 1H NMR (400MHz, CDCl3) delta 1.29-1.37 (m, 2H), 1.47 (s, 9H), 1.62-1.69 (m, 2H), 1.92-1.95 (m, 4H), 2.30-2.34 (m, 2H), 3.05-3.10 (m, 2H), 3.87-3.92 (m, 2H).

References: [1]Patent: US2005/70609,2005,A1 .Location in patent: Page/Page column 51-52; 58.
[2]Patent: WO2007/3965,2007,A1 .Location in patent: Page/Page column 28-29.

4
[ 123-38-6 ]
[ 191805-29-5 ]
[ 849203-10-7 ]

Yield	Reaction Conditions	Operation in experiment
		tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Step G (4.5 g, 17.8 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in tetrahydrofuran (100 mL), and cooled to -78 C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (24 mL, 36 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 30 min at -78 C. before adding propionaldehyde (2.6 mL, 36 mmol). After 5 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20-30% ethyl acetate in hexanes to give the title compound (4.75 g). 1H NMR (400 MHz, CDCl3): delta 0.97 (t, 3 H), 1.33-1.37 (m, 2 H), 1.47 (s, 9 H), 1.54-1.68 (m, 5 H), 1.75-1.78 (m, 1 H), 2.07-2.13 (m, 2 H), 2.30-2.33 (m, 1 H), 2.95-3.15 (m, 2 H), 3.62-3.63 (m, 1 H), 3.84-3.94 (m, 2 H).
		1,1-Dimethylethyl l-oxo-8-azaspiro[4.5]decane-8-carboxylate (Description 52, 4.5 g, 17.8 mmol) was dried by adding and evaporating toluene (3 x 10 mL) under reduced pressure, dissolved in THF (100 mL) and cooled to -78 0C. Lithium diisopropylamide mono(tetrahydrofuran) (1.5M in cyclohexane, 24 mL, 36 mmol,) was added and the mixture was stirred at -78 0C for 30 min. Propionaldehyde (2.6 mL, 36 mmol) was added and the mixture was stirred at -78 0C for 5 min. The mixture was diluted with Et2O, poured into saturated aqueous ammonium chloride and extracted with Et2O (3x). The combined organic fractions were washed with brine, dried (Na2SO4), filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography, eluting with 20-30% EtOAc in hexanes, to give the title compound (4.75 g).1H NMR (400MHz, CDCl3) delta 0.97 (t, 3H), 1.33-1.37 (m, 2H), 1.47 (s, 9H), 1.54-1.68 (m, 5H), 1.75-1.78 (m, IH), 2.07-2.13 (m, 2H), 2.30-2.33 (m, IH), 2.95-3.15 (m, 2H), 3.62-3.63 (m, IH), 3.84-3.94 (m, 2H).

References: [1]Patent: US2005/70609,2005,A1 .Location in patent: Page/Page column 52; 58-59.
[2]Patent: WO2007/3965,2007,A1 .Location in patent: Page/Page column 29.

5
[ 75-07-0 ]
[ 191805-29-5 ]
[ 849203-23-2 ]

Yield	Reaction Conditions	Operation in experiment
		tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (1.2 g, 4.70 mmol) was dried by evaporating with toluene (5 mL) three times in vacuo, dissolved in tetrahydrofuran (50 mL), and cooled to -78 C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (6.3 mL, 9.4 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 35 min at -78 C. before adding acetaldehyde (0.527 mL, 9.4 mmol). After 10 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20-40% ethyl acetate/hexanes to give the title compound (0.620 g). 1H NMR (400 MHz, CDCl3): delta 1.20 (d, 3 H), 1.31-1.37 (m, 2 H), 1.47 (s, 9 H), 1.52-1.81 (m, 4 H), 2.06-2.14 (m, 2 H), 2.25 (q, 1 H), 2.96-3.11 (m, 2 H), 3.79-3.96 (m, 3 H).

References: [1]Patent: US2005/70609,2005,A1 .Location in patent: Page/Page column 52; 60.

6
[ 191805-29-5 ]
[ 109-94-4 ]
C₁₅H₂₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tert-butyl methyl ether; at -78℃; for 48h;	tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to -78 C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min.

References: [1]Patent: US2005/70609,2005,A1 .Location in patent: Page/Page column 52; 62.

7
[ 191805-29-5 ]
[ 74-88-4 ]
racemic tert-butyl 2-methyl-1-oxo-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.3 g		To a solution of fer?-butyl l-oxo-8-azaspiro[4.5]decane-8-carboxylate (2.2 g, 8.68 mmol) in THF (24 mL) was added LiHMDS (1 M in THF, 8.68 mL, 8.68 mmol) at 0- 5 C. After stirring the mixture for 30 min at this temperature, iodomethane (0.543 mL, 8.68 mmol) was added. The resulting mixture was allowed to warm to RT and stirred for 2 h. The reaction mixture was diluted with EtO Ac and quenched with sat. aq NaHCC^. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting brown oil was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to give fer?-butyl 2-methyl-l-oxo-8-azaspiro[4.5]decane-8-carboxylate (1.3 g, 4.86 mmol). MS m/z 268.1. (M+H)+.
1.3 g		Step a: To a solution of tert-butyl 1 -oxo-8-azaspiro[4.Sjdecane-8-carboxylate (2.2 g, 8.68 mmol) in THF (24 mL) was added LHMDS (1 M in THF, 8.68 mL, 8.68 mmol) at 0-5C. After stirring the mixture for 30 mm at this temperature, iodomethane (0.543 mL, 8.68 mmol) was added. The resulting mixture was allowed to warm to RT and stirred for additional 2 h. The reaction mixture was diluted with EtOAc and sat. aq. NaHCO3. The organic phase was washed with brine, dried over Na2504, filtered and concentrated under reduced pressure. The resulting brown oil was purified by silica chromatography (0 to 25% gradient of EtOAc/heptane) to give racemic tert-butyl 2-methyl-1-oxo-8-azaspiro[4.Sjdecane-8-carboxylate (1.3 g, 4.86 mmol). MS m/z 268.1. (M+H).
1.3 g		Intermediate B-21 ( R)-tert -butyl 1 -((R)- 1 , 1 -dimethylethylsulfinamino)-2-methyl-8-azaspiro[4.51decane-8- carboxylate Step a: To a solution of ferf-butyl l-oxo-8-azaspiro[4.5]decane-8-carboxylate (2.2 g, 8.68 mmol) in THF (24 mL) was added LHMDS (1 M in THF, 8.68 mL, 8.68 mmol) at 0-5 C. After stirring the mixture for 30 min at this temperature, iodomethane (0.543 mL, 8.68 mmol) was added. The resulting mixture was allowed to warm to RT and stirred for additional 2 h. The reaction mixture was diluted with EtOAc and sat. aq. NaHC(. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting brown oil was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to give racemic ferf-butyl 2-methyl-l-oxo-8-azaspiro[4.5]decane-8-carboxylate (1.3 g, 4.86 mmol). MS m/z. 268.1. (M+H)+.

1.3 g

To a solution of tert-butyl 1-oxo-8-azaspiro [4.5]decane-8-carboxylate (2.2 g, 8.68 mmol) in THF (24 mE) was added LiHMDS (1 M in THF, 8.68 mE, 8.68 mmol) at 0-5 C. Afier stirring the mixture for 30 mm at this temperature, iodomethane (0.543 mE, 8.68 mmol) was added. The resulting mixture was allowed to warm to RT and stirred for 2 h. The reaction mixture was diluted with EtOAc and quenched with sat. aq NaHCO3. The organic phase was washed with brine, dried over Na2504, filtered and concentrated under reduced pressure. The resulting brown oil was purified by silica chromatography (0 to 25% gradient of EtOAc/heptane) to give tert-butyl 2-methyl-i -oxo-8- azaspiro[4.5]decane-8-carboxylate (1.3 g, 4.86 mmol). MS mlz 268.1. (M+H).

References: [1]Patent: WO2015/107495,2015,A1 .Location in patent: Paragraph 00333.
[2]Patent: WO2016/203405,2016,A1 .Location in patent: Paragraph 00342.
[3]Patent: WO2016/203406,2016,A1 .Location in patent: Paragraph 00343.
[4]Patent: US2017/15680,2017,A1 .Location in patent: Page/Page column 0385; 0386.

8
[ 191805-29-5 ]
racemic tert-butyl 2-fluoro-1-oxo-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]
tert-butyl 2,2-difluoro-1-oxo-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
351 mg; 573 mg		To a -78 C solution of NaHMDS (1 M in THF, 8.68 mL, 8.68 mmol) was added a solution of fer?-butyl l-oxo-8-azaspiro[4.5]decane-8-carboxylate (2.0 g, 7.89 mmol) in THF (5 mL). After stirring for 30 min at this temperature, a solution of N- fluorobenzenesulfonamide (2.49 g, 7.89 mmol) in THF (10 mL) was added. After 3 h stirring at - 78 C, it was diluted with sat. aq NaHC03 (100 mL) and extracted with DCM (3 x 100 mL). The combined organic phases were washed with brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to give racemic fer?-butyl 2-fluoro-l-oxo-8-azaspiro[4.5]decane-8- carboxylate (351 mg, 1.29 mmol). MS m/z 272.1 (M+H)+ and difluoro ketone which coelutes with starting material. The combined coeluted fractions of difluoro ketone/starting were repurified by silica chromatography (0 to 5% gradient of MeOH/DCM) to give fer?-butyl 2,2-difluoro-l- oxo-8-azaspiro[4.5]decane-8-carboxylate (573 mg, 1.98 mmol). MS m/z 290.1 (M+H)+.

References: [1]Patent: WO2015/107495,2015,A1 .Location in patent: Paragraph 00329.

9
[ 191805-29-5 ]
(1R)-tert-butyl 1-((R)-1,1-dimethylethylsulfinamido)-2-methyl-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

References: [1]Patent: WO2015/107495,2015,A1 .
[2]Patent: WO2016/203405,2016,A1 .
[3]Patent: WO2016/203406,2016,A1 .

10
[ 191805-29-5 ]
8-(6-amino-5-((2-(trifluoromethyl)pyridin-3-yl)thio)pyrazin-2-yl)-8-azaspiro[4.5]decan-1-amine [ No CAS ]

References: [1]Patent: WO2015/107495,2015,A1 .
[2]Patent: WO2016/151501,2016,A1 .
[3]Patent: US2017/15680,2017,A1 .

11
[ 191805-29-5 ]
(R)-8-(6-amino-5-((2-(trifluoromethyl)pyridin-3-yl)thio)pyrazin-2-yl)-8-azaspiro[4.5]decan-1-amine [ No CAS ]
(S)-8-(6-amino-5-((2-(trifluoromethyl)pyridin-3-yl)thio)pyrazin-2-yl)-8-azaspiro[4.5]decan-1-amine [ No CAS ]

References: [1]Patent: WO2015/107495,2015,A1 .
[2]Patent: WO2016/151501,2016,A1 .
[3]Patent: US2017/15680,2017,A1 .

12
[ 191805-29-5 ]
racemic tert-butyl 1-(1,1-dimethylethylsulfinamido)-2,2-difluoro-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

References: [1]Patent: WO2015/107495,2015,A1 .
[2]Patent: WO2016/203405,2016,A1 .
[3]Patent: WO2016/203406,2016,A1 .
[4]Patent: US2017/15680,2017,A1 .

13
[ 191805-29-5 ]
N-(2,2-difluoro-8-azaspiro[4.5]decan-1-yl)-2-methylpropane-2-sulfinamide [ No CAS ]

References: [1]Patent: WO2015/107495,2015,A1 .
[2]Patent: US2017/15680,2017,A1 .

14
[ 191805-29-5 ]
N-(8-(6-amino-5-((2-(trifluoromethyl)pyridin-3-yl)thio)pyrazin-2-yl)-2,2-difluoro-8-azaspiro[4.5]decan-1-yl)-2-methylpropane-2-sulfinamide [ No CAS ]

References: [1]Patent: WO2015/107495,2015,A1 .
[2]Patent: US2017/15680,2017,A1 .

15
[ 191805-29-5 ]
(R)-N-(8-(6-amino-5-((2-(trifluoromethyl)pyridin-3-yl)thio)pyrazin-2-yl)-2,2-difluoro-8-azaspiro[4.5]decan-1-yl)-2-methylpropane-2-sulfinamide [ No CAS ]