[ CAS No. 561314-57-6 ] {[proInfo.proName]}

Name: 561314-57-6|2,8-Diazaspiro[4.5]decan-3-one|95%
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Quality Control of [ 561314-57-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 561314-57-6 ]

CAS No. :	561314-57-6	MDL No. :	MFCD11044206
Formula :	C₈H₁₄N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASPBBYVNTMIKLA-UHFFFAOYSA-N
M.W :	154.21	Pubchem ID :	10559599
Synonyms :

Safety of [ 561314-57-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 561314-57-6 ]

* 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 [ 561314-57-6 ]
Downstream synthetic route of [ 561314-57-6 ]

[ 561314-57-6 ] Synthesis Path-Upstream 1~5

1
[ 169206-67-1 ]
[ 561314-57-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trifluoroacetic acid In dichloromethane at 30℃; for 12 h;	Example 3C (920 mg, 3.62 mmol) in DCM /TFA (5mL / 5mL) mixture. Stirred for 12 hours at 30 deg.C. TLC (PE: ethyl acetate = 1: 1) showed complete. The reaction mixture was concentrated under reduced pressure to give the crude product, the crude product was dissolved in water (30 mL) with sodium hydroxide solution(1N) was adjusted to pH 10; the mixture was extracted with dichloromethane(15mL × 4). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give the title compound (550mg, yield 98percent) as a yellow oil.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2288 - 2294
[2] Patent: CN105330698, 2016, A, . Location in patent: Paragraph 0232; 0233; 0234; 0235

2
[ 945892-88-6 ]
[ 561314-57-6 ]

Reference： [1] Patent: US2009/181996, 2009, A1, . Location in patent: Page/Page column 25

3
[ 79099-07-3 ]
[ 561314-57-6 ]

Reference： [1] Patent: CN105330698, 2016, A,

4
[ 135716-08-4 ]
[ 561314-57-6 ]

Reference： [1] Patent: CN105330698, 2016, A,

5
[ 1462385-41-6 ]
[ 561314-57-6 ]

Reference： [1] Patent: CN105330698, 2016, A,

[ 561314-57-6 ] Synthesis Path-Downstream 1~29

1
[ 561314-57-6 ]
[ 847233-56-1 ]
[ 945893-14-1 ]

Yield	Reaction Conditions	Operation in experiment
50%		Example 68A1-Cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-{3-oxo-2,8-diazaspiro[4,5]decan-8-yl}-1,4-dihydroquinoline-3-carboxylic Acid; From 99 mg (0.52 mmol) of <strong>[561314-57-6]3-oxo-2,8-diazaspiro[4,5]decane</strong> hydrochloride (Example 13A) the free base is liberated by stirring with 1 g of tris(aminoethyl)polystyrene in dichloromethane/methanol 10:1 for 20 minutes and subsequent filtration and removal of the solvents on a rotary evaporator. The residue is taken up in 3 ml of acetonitrile and stirred with 89 mg (0.26 mmol) of (T-4)-(1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolincarboxylato-O3,O4)boron difluoride (for preparation see: Journal of Medicinal Chemistry (1995), 38(22), 4478-4487) at 50 C. overnight. The solvent is removed on a rotary evaporator and the residue is taken up in 3 ml of triethylamine and 30 ml of ethanol and heated at reflux for 1.5 h. After cooling, the solvents are removed on a rotary evaporator and the residue is taken up in a little DMSO and purified by RP-HPLC (method 5). 56 mg (50% of theory) of the title compound are obtained.LC-MS (method 3): Rt=1.92 min, MS (ES+)=430 (M+H)+.1H NMR (400 MHz, CDCl3): delta=0.97-1.03 (m, 2H), 1.18-1.27 (m, 2H), 1.86 (t, J=5.3 Hz, 4H), 2.35 (s, 2H), 3.32 (s, 2H), 3.33-3.43 (m, 4H), 3.79 (s, 3H), 4.03 (m, 1H), 5.50 (s, 1H), 7.89 (d, J=12.2 Hz, 1H), 8.82 (s, 1H), 14.73 (s, 1H)

Reference： [1]Patent: US2009/181996,2009,A1 .Location in patent: Page/Page column 25

2
[ 945892-88-6 ]
[ 561314-57-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(aminoethyl)polystyrene; In methanol; dichloromethane;	Example 68A1-Cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-{3-oxo-2,8-diazaspiro[4,5]decan-8-yl}-1,4-dihydroquinoline-3-carboxylic Acid; From 99 mg (0.52 mmol) of 3-oxo-2,8-diazaspiro[4,5]decane hydrochloride (Example 13A) the free base is liberated by stirring with 1 g of tris(aminoethyl)polystyrene in dichloromethane/methanol 10:1 for 20 minutes and subsequent filtration and removal of the solvents on a rotary evaporator. The residue is taken up in 3 ml of acetonitrile and stirred with 89 mg (0.26 mmol) of (T-4)-(1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolincarboxylato-O3,O4)boron difluoride (for preparation see: Journal of Medicinal Chemistry (1995), 38(22), 4478-4487) at 50 C. overnight. The solvent is removed on a rotary evaporator and the residue is taken up in 3 ml of triethylamine and 30 ml of ethanol and heated at reflux for 1.5 h. After cooling, the solvents are removed on a rotary evaporator and the residue is taken up in a little DMSO and purified by RP-HPLC (method 5). 56 mg (50% of theory) of the title compound are obtained.LC-MS (method 3): Rt=1.92 min, MS (ES+)=430 (M+H)+.1H NMR (400 MHz, CDCl3): delta=0.97-1.03 (m, 2H), 1.18-1.27 (m, 2H), 1.86 (t, J=5.3 Hz, 4H), 2.35 (s, 2H), 3.32 (s, 2H), 3.33-3.43 (m, 4H), 3.79 (s, 3H), 4.03 (m, 1H), 5.50 (s, 1H), 7.89 (d, J=12.2 Hz, 1H), 8.82 (s, 1H), 14.73 (s, 1H)

Reference： [1]Patent: US2009/181996,2009,A1 .Location in patent: Page/Page column 25

3
[ 561314-57-6 ]
[ 1297137-35-9 ]
[ 1609198-61-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2288 - 2294

4
[ 169206-67-1 ]
[ 561314-57-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trifluoroacetic acid; In dichloromethane; at 30℃; for 12h;	Example 3C (920 mg, 3.62 mmol) in DCM /TFA (5mL / 5mL) mixture. Stirred for 12 hours at 30 deg.C. TLC (PE: ethyl acetate = 1: 1) showed complete. The reaction mixture was concentrated under reduced pressure to give the crude product, the crude product was dissolved in water (30 mL) with sodium hydroxide solution(1N) was adjusted to pH 10; the mixture was extracted with dichloromethane(15mL × 4). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give the title compound (550mg, yield 98%) as a yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2288 - 2294
[2]Patent: CN105330698,2016,A .Location in patent: Paragraph 0232; 0233; 0234; 0235

5
[ 561314-57-6 ]
[ 1609198-62-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2288 - 2294

6
[ 561314-57-6 ]
[ 1446358-48-0 ]
C₂₅H₂₃F₂N₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In tetrahydrofuran; at 40℃; for 48h;	General procedure: General procedure B A solution of amino nucleophile (3 equiv.), triethylamine (10 equiv.), and Intermediate 1 (1 equiv.) was stirred in dioxane and water (2:1 ratio) at 90 C until complete consumption of starting material was observed by LC/MS. The solution was diluted withiN hydrochloric acid and dichloromethane. The layers were then separated and thelayer was extracted with dichloromethane. The organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Purification yielded theproduct The title compound was prepared following general procedure B, except <strong>[561314-57-6]2,8-diazaspiro[4.5]decan-3-one</strong> (2 equiv.) was the amine reactant, no triethylamine was used, and contents were heated to 40 C for 2 d as a solution in THF. The reaction was cooled, solvent was removed in vacuo, and the resulting solid was rinsed with iN HC1 solution to deliver the desired compound, Compound 1-30 (57.8 mg, 83% yield) as a white solid. 1H NMR (500 MHz, METHANOL-d4) oe ppm 8.86 (s, 1 H) 8.36 (d, 1 H) 7.71 (s, 1 H) 7.31 -7.37 (m, 1 H) 7.13 (dd, 2 H) 6.99 - 7.04 (m, 2 H) 6.06 (s, 2 H) 4.32 (br. s., 2 H) 4.13 (br. s., 2 H)3.37 (br. s., 2 H) 2.42 (s, 2 H) 1.95 (t, 4 H).

Reference： [1]Patent: WO2014/144100,2014,A2 .Location in patent: Paragraph 00274

7
[ 561314-57-6 ]
ethyl 6-oxo-3-azabicyclo[3.1.1]heptane-3-carboxylate [ No CAS ]
ethyl 6-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-3-azabicyclo[3.1.1]heptane-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2,8-Diazaspiro[4.5]decan-3-one (0.11 g, 0.72 mmol) and ethyl 6-oxo-3- azabicyclo[3.1.1]heptane-3-carboxylate (0.12 g, 0.65 mmol) were dissolved in DCM (6.5 mL). Titanium (IV) isopropoxide (0.35 mL, 1.17 mmol) was added and the reactionmixture was stirred at rt under nitrogen overnight. The reaction mixture was cooled to -78 00 and MeOH (15 mL) was added, the reaction mixture was stirred for 15 mm at -78 00 NaBH4 (0.18 g, 5.20 mmol) was added and the reaction mixture was stirred at -78 00 for 1 h then at rt under nitrogen overnight. The reaction mixture was treated withNaOH (1 M, 10 mL) and stirred for 30 mm. The precipitate was collected by filtration,washed with MeOH (3 x 20 mL) and the solvents were removed in vacuo. The residuewas purified by column chromatography (normal phase, [Biotage SNAP cartridge KPsil 25 g, 40-63 tim, 60 A, 25 mL per mm, gradient 0% to 10% MeOH in DCM]) to give a mixture of diastereomers of ethyl 6-(3-oxo-2 , 8-diazaspi ro[4. 5]dec-8-yl)-3- azabicyclo[3. 1.1 ]heptane-3-carboxylate. The mixture of diastereomers was purified bypreparative reversed phase HPLC (Phenomenex Gemini-NX 5 im 018 11OA Axia column, 100 x 30 mm, eluting with 15 to 50% MeON/Solvent B over 12.5 mm at 30 mLlmin [where solvent B is 0.2% of (28% NH3/H20) in H20] and collecting fractions by monitoring at 205 nm) to give ethyl 6-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-3- azabicyclo[3.1.1]heptane-3-carboxylate, Example 8-1 Isomer 1 (0.006 g, 2.9%) as acolourless solid and ethyl 6-(3-oxo-2 , 8-diazaspi ro[4. 5]dec-8-yl)-3-azabicyclo[3.1.1]heptane-3-carboxylate, Example 8-1 Isomer 2 (0.040 g, 19.2%) as acolourless solid.

Reference： [1]Patent: WO2015/140559,2015,A1 .Location in patent: Page/Page column 67

8
[ 561314-57-6 ]
C₁₆H₂₇N₃O [ No CAS ]

Reference： [1]Patent: WO2015/140559,2015,A1

9
[ 561314-57-6 ]
ethyl 3-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-9-azabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/140559,2015,A1

10
[ 561314-57-6 ]
4-nitrophenyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
(1,1-²H₂)ethyl 3-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/140559,2015,A1

11
[ 561314-57-6 ]
4-nitrophenyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
4-nitrophenyl 3-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.6%		2,8-Diazaspiro[4.5]decan-3-one (1.12 g, 7.24 mmol) and 4-nitrophenyl 3-oxo-8- azabicyclo[3.2.1]octane-8-carboxylate (2.10 g, 7.24 mmol) were dissolved in DCM (10 mL), treated with titanium (IV) isopropoxide (2.57 g, 9.05 mmol), then stirred at rt under nitrogen overnight. The reaction mixture was diluted with MeOH (30 mL) and NaCNBH3 (0.91 g, 14.48 mmol) was added and the reaction mixture was stirred at rtunder nitrogen overnight. Water (10 mL) and DCM (lOmL) were added and the solution was passed through a celite pad to remove solids. The filtrate was separated and the aqueous phase was extracted with DCM (3 x 25 mL). The organic phases were combined and washed with sat. NaHCO3 sol. (25 ml) and dried by passing down a Biotage Phase Separator cartridge. The solvents were removed in vacuo, and theresidue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 10 g, 40-63 tim, 60 A, 10 mL per mm, gradient 0% to 10% MeOH in DCM]) to give 4-nitrophenyl 3-(3-oxo-2 , 8-diazaspi ro[4. 5]dec-8-yl)-8- azabicyclo[3.2.1 ]octane-8-carboxylate, Intermediate 58 as a mixture of diastereoisomers, (204 mg, 6.6%) as a yellow glassy solid.

Reference： [1]Patent: WO2015/140559,2015,A1 .Location in patent: Page/Page column 47; 48

12
[ 561314-57-6 ]
[ 37778-51-1 ]
ethyl 5-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-2-azabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of ethyl 5-oxo-2-azabicyclo[2.2.2]octane-2-carboxylate (6.70 g, 34 mmol)and <strong>[561314-57-6]2,8-diazaspiro[4.5]decan-3-one</strong>l (5.24 g, 34 mmol) in DMF (30 mL) was addedHOAc (2.9 mL, 51 mmol) under nitgogen, the reaction mixture was stirred at rt for 20mi Na(OAc)3BH (21.60 g,102 mmol) was added and the reaction was stirred at45 0Cfor 3 d. Then the reaction mixture was warmed to 60 0C and stirred for another 24 h.The solvent was removed in vacuo and the residue was dissolved in water (20 mL)and basified with sat.NaHCO3. The aqueous layer was concentrated to dryness andthe resulting white solid was diluted with DCM (100 mL). The suspension was stirred atrt for 30 mm, filtered and the filter cake was washed with DCM (4 x 25 mL). Theorganic layers were combined and the solvent was removed in vacuo. The residuewas purified by preparative reversed phase HPLC (Instrument: Gilson, Column:Xbridge 21 .2250 mm C18, 10 um; Mobile Phase: A: water (10 mMol/L NH4HCO3) B:CAN); Flow rate(ml/min): 25.00) to give the two racemic isomers of ethyl 5-(3-oxo-2,8-diazaspi ro[4. 5]dec-8-yl)-2-azabicyclo[2 .2.2]octane-2-carboxylate. Which were furtherpurified by chiral SFC (Column: OJ-H, 4.6250mm; Co-solvent: MeOH(0.1% NH4OH);column temperature: 40;C02 flow rate: 2.55) to give ethyl 5-(3-oxo-2,8-diazaspi ro[4. 5]dec-8-yl)-2-azabicyclo[2 .2.2]octane-2-carboxylate, Example 3-1 Isomer1 (0.78 g, 6.9%) as a colourless solid, ethyl 5-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-2-azabicyclo[2.2.2]octane-2-carboxylate, Example 3-1 Isomer 2 (1.20 g, 10.5%) as acolourless solid, ethyl 5-(3-oxo-2, 8-diazaspi ro[4. 5]dec-8-yl)-2-azabicyclo[2 .2 .2]octane-2-carboxylate, Example 3-1 Isomer 3 (0.45 g, 3.9%) as a colourless solid and ethyl 5-(3-oxo-2, 8-diazaspiro[4. 5]dec-8-yl)-2-azabicyclo[2 .2.2]octane-2-carboxylate, Exam pie3-1 isomer 4 (1.30 g, 11.4%) as a colourless solid.

Reference： [1]Patent: WO2015/140559,2015,A1 .Location in patent: Page/Page column 65; 66

13
[ 561314-57-6 ]
prop-2-yn-1-yl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]
prop-2-yn-1-yl 3-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-9-azabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) isopropylate; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; for 32h;Reflux; Inert atmosphere;	2,8-Diazaspiro[4.5]decan-3-one (0.12 g, 0.75 mmol) and prop-2-yn-1-yl 3-oxo-9- azabicyclo[3.3.1]nonane-9-carboxylate (0.17 g, 0.75 mmol) were dissolved in DOE (7.5 mL) at rt and titanium isopropoxide (0.66 mL, 2.25 mmol) was added. The reactionmixture was heated to reflux under N2 for 16 h then cooled to rt. STAB (0.80 g, 3.75 mmol) was added, the reaction mixture again heated to reflux for 16 h then cooled to rt. The reaction mixture was quenched with the addition of sat. NaHCO3 sol. (10 mL), diluted with DCM (10 mL) then filtered through a pad of celite. The layers were separated and the aqueous layer was extracted with DCM (4 x 20 mL). The organiclayers were combined and washed with brine, then dried (Mg504). The solvents were removed in vacuo, and the residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 25 g, 40-63 tim, 60 A, 27 mL per mm, gradient 1% to 10% MeOH in DCM]) to give an inseparable mixture of diastereomers This mixture was purified by preparative reversed phase HPLC (Phenomenex Gemini-NX 5im 018 11OA Axia column, 100 x 30 mm, eluting with 15 to 35% MeCN/Solvent B over 14.4 mm at 30 mL/min [where solvent B is 0.2% of (28% NH3/H20) in H20] and collecting fractions by monitoring at 205 nm) to give prop-2-yn-1-yl 3-(3-oxo-2,8- diazaspi ro[4. 5]dec-8-yl)-9-azabicyclo[3. 3.1 ]nonane-9-carboxylate Example 5-2 Isomer 1 (0.02 g, 7%) as a colourless solid and prop-2-yn-1-yl 3-(3-oxo-2,8-diazaspi ro[4. 5]dec-8-yl)-9-azabicyclo[3.3. 1 ]nonane-9-carboxylate Example 5-2 Isomer2(0.03 g, 11%) as a colourless solid.

Reference： [1]Patent: WO2015/140559,2015,A1 .Location in patent: Page/Page column 59

14
[ 512822-27-4 ]
[ 561314-57-6 ]
tert-butyl 3-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-9-azabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) isopropylate; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane;Reflux; Inert atmosphere;	2,8-Diazaspiro[4.5]decan-3-one (0.15 g, 1.0 mmol) and tert-butyl 3-oxo-9- azabicyclo[3.3.1]nonane-9-carboxylate (0.25 g, 0.1.05 mmol) were dissolved in DOE(10.0 mL) at rt and titanium isopropoxide (0.89 mL, 3.0 mmol) was added. The reaction mixture was stirred overnight at reflux under N2, then cooled to room temperature. STAB (1.06 g, 5.0 mmol) was added, the reaction mixture again heated to reflux, maintained overnight and then cooled to room temperature. The reaction mixture was quenched with the addition of sat. NaHCO3 sol. (10 mL), diluted with DCM (10 mL)then filtered through a pad of celite. The layers were separated and the aqueous layer was extracted with DCM (4 x 20 mL). The organic layers were combined and washed with brine, then dried (Mg504). The solvents were removed in vacuo to give crude tertbutyl 3-(3-oxo-2 , 8-diazaspi ro[4. 5]dec-8-yl)-9-azabicyclo[3. 3.1 ]nonane-9-carboxylate which was used without any purification.LCMS (Method C): mlz 378 (M+H) (ES), at 1.54 mi UV active.

Reference： [1]Patent: WO2015/140559,2015,A1 .Location in patent: Page/Page column 60

15
[ 561314-57-6 ]
(±)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide [ No CAS ]
(±)-7,8-dimethoxy-N,4-dimethyl-1-[4-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl) phenyl]-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With chloro-(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)]palladium(II); sodium t-butanolate; In toluene; at 110℃; for 16h;Inert atmosphere;	Example 28 (±)-7,8-Dimethoxy-N,4-dimethyl-1-[4-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)phenyl]-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (0881) (0882) Under argon, 100 mg (0.231 mmol) of (±)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 30A), 31 mg (0.324 mmol) of sodium tert-butoxide and 39 mg (0.254 mmol) of <strong>[561314-57-6]2,8-diazaspiro[4.5]decan-3-one</strong> (CAS[561314-57-6] were initially charged in 4 ml of toluene, and the mixture was degassed by flushing with argon. 9.1 mg (0.012 mmol) of chloro-(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)]palladium(II) (CAS [1310584-14-5]) were then added, and the reaction mixture was degassed again, saturated with argon and then stirred at 110 C. for about 16 hours. After cooling, the mixture was added to sat. sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases were filtered through a water-separating filter and the solvents were removed on a rotary evaporator. The residue was purified by preparative RP-HPLC. This gave 16 mg (14% of theory) of the desired product as a solid. (0883) LCMS (method 1): Rt=0.74 min; m/z=506 (M+H)+ (0884) 1H-NMR (400 MHz, CDCl3): delta=1.03 (d, 3H), 1.73 (t, 6H), 2.59 (s, 2H), 2.80-3.0 (m, 4H), 2.91 (d, 3H), 3.10 (dd, 1H), 3.69 (s, 3H), 3.72 (s, 2H), 3.96 (s, 3H), 5.39-5.49 (m, 1H), 6.41-6.49 (m, 1H), 6.63 (s, 1H), 6.75 (s, 1H), 7.54 (d, 2H), 7.68 (d, 2H).

Reference： [1]Patent: US2016/129011,2016,A1 .Location in patent: Paragraph 0881; 0882; 0883; 0884

16
[ 79099-07-3 ]
[ 561314-57-6 ]