858671-91-7|tert-Butyl 2,5-Diazabicyclo[2.2.2]octane-2-carboxylate| Ambeed

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Quality Control of [ 858671-91-7 ] Purity: 98% SDS Specification

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Product Details of [ 858671-91-7 ]

CAS No. :	858671-91-7
Formula :	C₁₁H₂₀N₂O₂
M.W :	212.29
SMILES Code :	O=C(N1C(CC2)CNC2C1)OC(C)(C)C
MDL No. :	MFCD18249863
InChI Key :	RBLOMFQUEUBEBG-UHFFFAOYSA-N
Pubchem ID :	56973608

Safety of [ 858671-91-7 ]

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

Application In Synthesis of [ 858671-91-7 ]

* 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 [ 858671-91-7 ]

[ 858671-91-7 ] Synthesis Path-Downstream 1~35

1
[ 858671-91-7 ]
[ 73781-91-6 ]
C₁₈H₂₅N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5300 - 5309.

2
[ 24424-99-5 ]
[ 1192-92-3 ]
[ 858671-91-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydroxide; In water; isopropyl alcohol; at 0℃; for 1.5h;	A solution of di-tert-butyldicarbonate (6.5 mmol) in isopropanol (15 mL) was added drop wise to a solution of the diamine (7.06 mmol) in isopropanol (100 mL), water (35mL), and 1 M sodium hydroxide (6.5 mL) at 0 C. The reaction mixture was maintained for 1.5 h at 0 C and was concentrated to-50 ni-L. The aqueous slurry was saturated with solid sodium chloride and the pH adjusted to 10 with 2 M sodium hydroxide. The aqueous layer was extracted with ethyl acetate (3 x 35 mL) and the combined organic layers were washed with brine and dried (magnesium sulfate). The volatiles were removed under reduced pressure to afford the crude mono-protected diamine in 42% yield as a light yellow oil.

References: [1]Patent: WO2005/63767,2005,A2 .Location in patent: Page/Page column 52.

3
[ 858671-91-7 ]
[ 50-00-0 ]
C₁₂H₂₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; for 16.1667h;	Formaldehyde (37% aqueous solution, 7.43 mmol) and acetic acid (4.46 mmol) were added to a solution of the crude amine (2.97 mmol) in tetrahydrofuran (25 mL). Solid sodium triacetoxyborohydride (5.94 mmol) was added in small portions to the reaction mixture after 10 min and the reaction mixture was maintained for 16 h. The reaction mixture was diluted with a 10% aqueous sodium bicarbonate solution (100 mL) and was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were washed with brine, dried (magnesium sulfate), and concentrated to provide a light yellow residue. The residue was dissolved in dioxane (25 mL) and diluted with concentrated hydrochloric acid (12.5 mL). The volatiles were removed after 30 minutes, thus providing the mono- methyl bicyclic base in 40% yield as a colorless solid. The procedure for N-methylation and removal of the carbamate protecting group was used for the production of 2-methyl- 2,5-diazabicyclo [2.2. 1] heptane dihydrochloride. Literature references: Newman, H. J. Heterocyclic Chez. 1974, 11, 449. Sturm, P. A.; Henry, D. W. J. Med. Chemin. 1974, 17, 481. The following bases were prepared using this method: 2-Methyl-2,5-diazabicyclo [2.2. 2] octane dihydrochloride. (1S, 4S)-2-Methyl-2, 5-diazabicyclo [2.2. 1] heptane dihydrochloride.

References: [1]Patent: WO2005/63767,2005,A2 .Location in patent: Page/Page column 52.

4
[ 858671-91-7 ]
[ 1255206-68-8 ]
[ 1255208-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 150℃; for 1h;Microwave irradiation;	A mixture of 4-methyl-5 -oxiran-2-yl-2-benzofuran- 1 (3H)-one (700 mg, 3.68 mmol) and 1,1- dimethylethyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate (748 mgs 3.68 mmol) in 2 mL DMSO was heated under microwave condition (15O0C) for 1 hr. After cooling to rt, the mixture was diluted with water (50 mL), extracted with EtOAc (3 X 50 mL). The combined organic layers were washed with brine and dried over Na2SO45 then concentrated. The residue was purified by TLC (MeOHZDCM=I : 15) to obtain l,l-dimethylethyl5-[2-hydroxy-2-(4-methyl-l-oxo-l,3- dihydro-2-benzofuran-5-yl)ethyl]-2,5-diazabicyclo[2.2.2]octane-2-carboxylate as a mixture of 4 isomers, which was separated by SFC chiral chromatography to obtain four chiral isomers or isomer mixtures A, B, C and D with the same MS m/z 403 (M+l)+.

References: [1]Patent: WO2010/129379,2010,A1 .Location in patent: Page/Page column 83.

5
[ 858671-91-7 ]
[ 1276676-86-8 ]
[ 1276677-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; N,N-dimethyl acetamide;bis(tri-t-butylphosphine)palladium(0); at 100℃; for 18h;Inert atmosphere;	Anhydrous dimethylacetamide (85 mL, degassed prior to use) was added to a mixture of 5-chloro-l-(2,2-dimethylpropyl)-3-methyl-l,3-dihydro-2H-imidazo[4,5-¾]pyridin-2- one (1-4, 17.89 g, 70.5 mmol), potassium phosphate tribasic (30.1 g, 142 mmol), bis(tri-t- butylphosphine)palladium(O) (1.45 g, 2.84 mmol), and tert-butyl-2,5-diazabicyclo[2.2.2]octane- 2-carboxylate (15.81 g, 74.5 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 normal-phase chromatography (40% EtOAc in hexane) afforded tert-butyl-5-[l-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-lH- imidazo[4,5-b]pyridin-5-yl]-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (15-1) as a white solid. MS m/z (M+H): calculated = 430.2813; observed = 430.2807.

References: [1]Patent: WO2011/34741,2011,A1 .Location in patent: Page/Page column 71-72.

6
[ 858671-91-7 ]
[ 1276677-09-8 ]
[ 1276677-11-2 ]

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 (655 mL, degassed prior to use) was added to a mixture of 5 -chloro-3 -methyl- 1 -(4,4,4-trifluoro-2,2-dimethylbutyl)- 1 ,3-dihydro-2H-imidazo[4,5- £]pyridin-2-one (34-2, 175 mg, 0.544 mmol), potassium phosphate tribasic (231 mg, 1.09 mmol), bis(tri-t-butylphosphine)palladium(0) (11.2 mg, 0.02 mmol), and tert-butyl-2,5- diazabicyclo[2.2.2]octane-2-carboxylate (115 g, 0.54 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 normal-phasechromatography (40% EtOAc in hexane) afforded tert-butyl 5-[3-methyl-2-oxo-l -(4,4,4- trifluoro-2,2-dimethylbutyl)-2,3-dihydro-lH-imidazo[4,5-¾]pyridin-5-yl]-2,5- diazabicyclo[2.2.2]octane-2-carboxylate (34-3) as a white solid. MS m/z (Mu+Eta): calculated = 497.5; observed = 498.5.

References: [1]Patent: WO2011/34741,2011,A1 .Location in patent: Page/Page column 123-124.

7
[ 858671-91-7 ]
rac-benzyl ((2S,3R,4R)-1-acetyl-6-bromo-2,3-dimethyl-1,2,3,4-tetrahydrociuinolin-4-yl)carbamate [ No CAS ]
tert-butyl 5-((rac-2S,3R,4R)-1-acetyl-4-amino-23-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.6%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃;Inert atmosphere;	A mixture of rac-benzyl ((2S,3R,4R)- I -acetyl-6-bromo-2,3-dimethyl- I ,2,3,4-tetrahydroq uinolin-4-yl)carbamate (for a preparation see Intermediate 3, 73.5 mg, 0.170 mmol), <strong>[858671-91-7]tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate</strong> (43.8 mg, 0.206 mmol), sodium-tert-butoxide (49.4 mg,0.514 mmol), DavePhos (13.6 mg, 0.035 mmol) and Pd2(dba)3 (15.5 mg, 0.017 mmol) had 1,4-dioxane (2 mL) added and were heated with stirring under nitrogen at 100 C. The reaction mixture was allowed to cool to rt and filtered through a celite cartridge which was flushed with ethyl acetate, the filtrate was concentrated and purified by MDAP (Formic) to give the product (12.9 mg, 0.030 mmol, 17.66%) as a cream solid. This was a racemic mixture of diatereoisomers.LCMS (2 mm Formic): Rt = 0.77 mi [MH] = 429.

References: [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 92.

8
[ 858671-91-7 ]
[ 5339-26-4 ]
2,5-bis[2-(4-nitrophenyl)ethyl]-2,5-diazabicyclo[2.2.2]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a flask charged with <strong>[858671-91-7]tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate</strong> (200 mg, 0.94 mmol) and a stir bar was added TFA (5 mL). The mixture was allowed to stir at RT for 2 hours. The volatiles were removed under reduced pressure. To the residue was added 1-(2-bromoethyl)-4-nitrobenzene (650 mg, 2.8 mmol), tetrabutylammonium iodide (35 mg, 0.094 mmol), K2CO3 (521 mg, 3.8 mmol), and DMF (5 mL). The mixture was heated to 80 C for 16 hours. LC showed formation of the desired product, which was separated by mass-directed HPLC. LC-MS (IE, m/z): 411 [M+1]+. (0.21 muM)

References: [1]Patent: EP2632465,2015,B1 .Location in patent: Paragraph 0301.

9
[ 858671-91-7 ]
[ 850589-47-8 ]
[ 589-87-7 ]
tert-butyl 5-[3'-chloro-4’-(dimethylcarbamoyl)biphenyl-4-yl]-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44 mg		A mixture of tert-butyl 2,5-diazabicyclo[2.2.2joctane-2-carboxylate (1.29 g, 6.08 mmol), p15 bromoiodobenzene (1.89 g, 6.68 mmol), CuT (1.16 g, 6.08 mmol), Cesium Carbonate (7.9 g, 24.3mmol), and 2-(2-methyl-1-oxopropyl)cyclohexanone (2.03 mL, 12.15 mmol) was stirred in DMF (20.3 mL) at 100 C overnight. The mixture was then extracted with EtOAc and water, the organic layer was dried over magnesium sulfate, and the solvents were removed in vacuo to give crude product which was purified by silica gel chromatography (0-30% EtOAc/hexanes) andreverse phase chromatography (20-95% ACN/water with 0.1% TFA) to yield an inseparable mixture of tert-butyl 5 -(4-bromophenyl)-2,5-diazabicyclo[2.2. 21 octane-2-carboxylate ; A mixture of products from step 1 (tert-butyl 5-(4-bromophenyl)-2,5-diazabicyclo [2.2.2j octane2-carboxylate and tert-butyl 5-(4-iodophenyl)-2,5-diazabicyclo [2.2.2j octane-2-carboxylate) (283 mg), 3-chloro-4-dimethylcarbamoylphenylboronic acid (210 mg, 0.925 mmol), sodium carbonate (2M, 0.96 mL, 1.9 mmol) in ACN (3.8 mL) was degassed by bubbling N2 for 15 mm.Bis(triphenylphosphine)palladium(II) chloride (21.6 mg, 0.03 mmol) was added and the mixture was stirred at 70C overnight. The mixture was then extracted with EtOAc and 5% aq. KHSO4, the organic layer was dried over magnesium sulfate, and the solvents were removed in vacuo to give crude product which was purified by silica gel chromatography (0-100% EtOAc/hexanes) and reverse phase chromatography (25-95% ACN/water with 0.1% TFA) to yield tert-butyl 5-(3?-chloro-4?-(dimethylcarbamoyl)-[1 , 1 ?-biphenylj-4-yl)-2,5-diazabicyclo[2.2.21 octane-2- carboxylate (44 mg). LRMS m/z (M+H) 470.3 found, 470.2 required.

References: [1]Patent: WO2017/83216,2017,A1 .Location in patent: Page/Page column 63.

10
[ 858671-91-7 ]
[ 850589-47-8 ]
[ 589-87-7 ]
tert-butyl 5-[3,3‘-dichloro-4’-(dimethylcarbamoyl)biphenyl-4-yl]-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]

References: [1]Patent: WO2017/83216,2017,A1 .

11
[ 858671-91-7 ]
[ 589-87-7 ]
tert-butyl 5-(4-bromophenyl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]
tert-butyl 5-(4-iodophenyl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
283 mg	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 100℃;	A mixture of tert-butyl 2,5-diazabicyclo[2.2.2joctane-2-carboxylate (1.29 g, 6.08 mmol), p15 bromoiodobenzene (1.89 g, 6.68 mmol), CuT (1.16 g, 6.08 mmol), Cesium Carbonate (7.9 g, 24.3mmol), and 2-(2-methyl-1-oxopropyl)cyclohexanone (2.03 mL, 12.15 mmol) was stirred in DMF (20.3 mL) at 100 C overnight. The mixture was then extracted with EtOAc and water, the organic layer was dried over magnesium sulfate, and the solvents were removed in vacuo to give crude product which was purified by silica gel chromatography (0-30% EtOAc/hexanes) andreverse phase chromatography (20-95% ACN/water with 0.1% TFA) to yield an inseparable mixture of tert-butyl 5 -(4-bromophenyl)-2,5-diazabicyclo[2.2. 21 octane-2-carboxylate [LRMS m/z (M+H) 367.2 found, 367.1 required.jwith tert-butyl 5-(4-iodophenyl)-2,5-diazabicyclo [2.2.21 octane-2-carboxylate [LRMS m/z (M+H) 415.2 found, 415.1 required.j (283 mg).

References: [1]Patent: WO2017/83216,2017,A1 .Location in patent: Page/Page column 63.

12
[ 858671-91-7 ]
5-[(3R,5R)-1-(2-chloroacetyl)-5-methylpiperidin-3-yl]quinoline-8-carbonitrile [ No CAS ]
5-[(3R,5R)-1-(2-2,5-diazabicyclo[2.2.2]oct-2-ylacetyl)-5-methylpiperidin-3-yl]quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To 5-[(3R,5R)- 1 -(2-Chloro-acetyl)-5-methyl-piperidin-3- ylj-quinoline-8-carbonitrile (50 mg; 0.15 mmol) in CAN (1 ml) was added DIEA (0.05 ml; 0.31 mmol) and tert-butyl 2,5-diazabicyclo [2.2.2j octane-2-carboxylate (39mg, 0.1 8mmol). The reaction mixture was stirred at 80C for 1 hr. The completed reaction was concentrated. The residue was added DCM (0.5 ml) and Trifluoro-acetic acid (347mg; 3.05 mmol; 20.00 eq.). The mixture was stirred at RT for 1 hr.The completed reaction was concentrated. The residue was added 30 ml of DCM and 5 ml of 5% aq Na2HCO3. The separated organic layer was washed with brine, dried and concentrated to yield the title compound as a white wax solid. Compound 116: LC-MS (M+1) = 404. NMR (400 MHz, Methanol-d4) 9.05 (d, I =4.6 Hz, 1H), 8.93 - 8.80 (m, 1H), 8.25 (dd, I = 7.7, 4.3 Hz, 1H), 7.83 - 7.65 (m, 2H), 4.77 (d, I =12.9 Hz, 1H), 4.29 (d, I = 13.5 Hz, 1H), 4.24 - 4.07 (m, 1H), 3.87 - 3.69 (m, 1H), 3.65 - 3.52 (m,2H), 3.52 - 3.38 (m, 2H), 3.15 - 2.95 (m, 3H), 2.95 - 2.76 (m, 2H), 2.76 - 2.57 (m, 1H), 2.45 -2.31 (m, 1H), 2.16 (d, I = 13.1 Hz, 2H), 2.08 - 1.95 (m, 1H), 1.80 - 1.64 (m, 2H), 1.17 - 1.01 (m,3H).

References: [1]Patent: WO2018/31434,2018,A1 .Location in patent: Paragraph 00198; 00412; 00413.

13
[ 858671-91-7 ]
C₈H₄BrClN₂ [ No CAS ]
C₁₉H₂₃BrN₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	General procedure: To a solution of 7 (150mg, 0.61mmol) in DMF (5mL) was added K2CO3 (256.6mg, 1.8mmol) and N-methyl piperazine (0.3mL, 3.0mmol). After heating at 80C for 4h, the reaction mixture was cooled to room temperature, poured in to cold water (20mL) and extracted with EtOAc (2×50mL). The combined organic layer was washed with water, brine, dried over Na2SO4 and concentrated to afford 3-bromo-2-(4-methylpiperazin-1-yl)-1,5-naphthyridine

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 610 - 621.

14
[ 858671-91-7 ]
C₃₁H₃₃F₃N₈O₃S [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 610 - 621.

15
[ 858671-91-7 ]
1-(5-(2-(2,5-diazabicyclo[2.2.2]octan-2-yl)-1,5-naphthyridin-3-yl)-4-(4-(trifluoro-methyl)thiazol-2-yl)pyridin-2-yl)-3-ethylurea [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 610 - 621.

16
[ 858671-91-7 ]
C₂₀H₂₇N₃ [ No CAS ]