[ CAS No. 658-24-2 ] {[proInfo.proName]}

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Quality Control of [ 658-24-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 658-24-2 ]

Product Details of [ 658-24-2 ]

CAS No. :	658-24-2	MDL No. :	MFCD08694643
Formula :	C₆H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	112.17	Pubchem ID :	-
Synonyms :

Safety of [ 658-24-2 ]

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Application In Synthesis of [ 658-24-2 ]

* 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 [ 658-24-2 ]

[ 658-24-2 ] Synthesis Path-Downstream 1~20

1
[ 116163-13-4 ]
[ 658-24-2 ]
[ 116162-82-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1344 - 1352

2
[ 116163-18-9 ]
[ 658-24-2 ]
[ 125197-56-0 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1344 - 1352

3
[ 125290-83-7 ]
[ 658-24-2 ]
1-Cyclopropyl-7-(2,5-diaza-bicyclo[2.2.2]oct-2-yl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 518 - 525

4
[ 132195-59-6 ]
[ 658-24-2 ]
7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 518 - 525

Yield	Reaction Conditions	Operation in experiment
		represents the ring bound over the nitrogen atom of the following ring systems; ... 7-azabicyclo[2.2.1]heptane, 2,5-diazabicyclo[2.2.1]heptane, 2-azabicyclo[2.2.2]octane, 8-azabicyclo[3.2.1]octane, 2,5-diazabicyclo[2.2.2]octane, indoline, isoindoline, (1H)-dihydroquinoline, ...

6
[ 626-55-1 ]
[ 24424-99-5 ]
[ 658-24-2 ]
[ 286946-82-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3627 - 3644

7
[ 623588-14-7 ]
[ 658-24-2 ]
C₂₃H₂₉N₅O₃ [ No CAS ]

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

8
[ 658-24-2 ]
C₁₁H₁₅N₃*2.2HCl [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3627 - 3644

9
[ 658-24-2 ]
[ 136123-89-2 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1344 - 1352

10
[ 626-55-1 ]
[ 658-24-2 ]
2-(3-pyridinyl)-2,5-diazabicyclo[2.2.2]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 75℃; for 2h;	Example 42A tert-butyl 5-(3-pyridinyl)-2,5-diazabicylo[2.2.2]octane-2-carboxylate 2-5-Diazabicyclo[2.2.2]octane (390 mg, 3.5 mmole), prepared by the method of Sturm and Henry (J. Med. Chem. (1974), 17,481), was treated with 3-bromopyridine (545 mg, 3.5 mmole), BINAP (92 mg, 0.14 mmole), Pd2(dba)3 (40 mg, 0.07 mmole) and sodium tert-butoxide (431 mg 4.5 mmole) in toluene (10 mL) under a nitrogen atmosphere. After heating the mixture at 75 C 5 C for 2 hours, the mixture was allowed to cool to ambient temperature and treated with di-tert-butyl-dicarbonate (1.5 g, 6.9 mmole) and then allowed to stir an additional 16 hours. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, hexanes:ethyl acetate 9:1 to1:1) to provide the title compound (193 mg, 19% yield). MS (DCI/NH3) m/z 290 (M+H)+, 307 (M+NH4)+.

Reference： [1]Patent: EP1147112,2003,B1 .Location in patent: Page/Page column 31

11
[ 103994-99-6 ]
[ 138808-69-2 ]
[ 658-24-2 ]
1-(4-Fluorophenyl)-6-fluoro-1,4-dihydro-7-(2,5-diazabicyclo[2.2.2]oct-yl)-4-oxo-3-quinolinecarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In pyridine;	EXAMPLE 30 1-(4-Fluorophenyl)-6-fluoro-1,4-dihydro-7-(2,5-diazabicyclo[2.2.2]oct-yl)-4-oxo-3-quinolinecarboxylic acid (R1 =H; Y=4-fluorophenyl; A=CH; R2 =c; n=2; Q=H) By the method of Example 28, 6,7,-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (957 mg, 3.0 mmol) and <strong>[658-24-2]2,5-diazabicyclo[2.2.2]octane</strong> (772 mg. 6.89 mmol) were reacted in pyridine (20 mL) at 80 C. for 24 hours to give a pale yellow solid (1.15 g, 94% yield); m.p. 285-286 C.

Reference： [1]Patent: US5091383,1992,A

12
[ 658-24-2 ]
[ 126202-23-1 ]
[ 1076206-57-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 130. 2-[(2^5-Trifluorophenyl)methyl]-2,5-diazabicyclo[2.2.2]octaiie (130); 0516] A stirred solution of piperazine 129 (216 mg, 1.93 mmol) in DCE (10 mL) was treated with AcOH (1 mL) and 2,3,5-trifluorobenzaldehyde (62 mg, 0.39 mmol). On stirring at rt for 30 min, STAB (83 mg, 0.39 mmol) was added in one portion and the reaction stirred a further 1.5 h at rt. Reaction progress was monitored by LC/MS. Two further additions of 2,3,5-trifluorobenzaldehyde (31 mg, 0.195 mmol) then took place 1.5 h apart; each was followed 30 min later with a portion of STAB (42 mg, 0.195 mmol). After stirring at rt an additional 1 h, the reaction was diluted with satd NaHCO3 (25 mL) and extracted into DCM (3 x 25 mL). The combined organic phases were dried (Na2SO4), filtered and evaporated to give the crude product which was purified by column chromatography (silica gel, 5-20% MeOH in DCM followed by 7 M NH3 in MeOH) to afford the title compound as a pale yellow oil: LC/MS tR 1.01 min; MS (ES+) m/z 257; 1H NMR deltaH (250 MHz, CDCl3) 6.95 (IH, m), 6.79 (IH, m), 3.74 (2H, s), 3.37 (2H, obs m), 3.08 (2H, d), 2.78 (2H, m), 2.10 (2H, m), 1.76 (2H, m).

Reference： [1]Patent: WO2008/134035,2008,A1 .Location in patent: Page/Page column 196

13
[ 1004-98-4 ]
[ 658-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran;Reflux;	A suspension of 2,5-diazabicyclo[2.2.2]octane-3,6-dione (100 mg, 0.714 mmol) in THF (20 mL) was added dropwise toiM LiAIH4 in THF (3.57 mL, 3.57 mmol) at reflux The resulting mixture was stirred at reflux overnight. The reaction was cooled to 000 in an ice bath.Water (0.2 mL) was added followed by 1M NaOH solution (1.2 mL) and the mixture stirred for 10 mm. Sodium sulphate was added and the mixture stirred for 10 mm. The reaction mixture was filtered through Celite (filter material) and the filter pad washed with THF (3x50 mL). The filtrate and washings were combined and concentrated in vacuo to give the title compound as a yellow gum which was used directly without further purification.
		Example 129. 2,5-Diazabicyclo [2.2.2] octane (129); [0515] A soxhlet extractor thimble was charged with diketopiperazine 128 (100 mg,0.71 mmol), then placed inside a soxhlet suspended above a flask containing a solution of LAH (4.3 mL, 4.30 mmol, 1.0 M in THF) in THF (100 mL). The system was then heated at reflux for 16 h. Once cooled to 0 0C, the reaction mixture was quenched via the addition of water (200 muL), 4 M NaOH (200 muL) then more water (600 muL). On stirring the resultant suspension at rt for 1 h, the mixture was dried (Na2SO4), filtered, and the filter cake washed with THF (100 mL). The combined filtrates were evaporated to afford <n="197"/>the title product as a pale yellow oil: 1H NMR deltaH (250 MHz, CDCl3) 4.95 (2H, br s), 3.20 (2H, dt), 3.02 (2H, dd), 2.79 (2H, m), 1.71-1.83 (4H, m).

Reference： [1]Patent: WO2015/8230,2015,A1 .Location in patent: Page/Page column 229
[2]Patent: WO2008/134035,2008,A1 .Location in patent: Page/Page column 195-196

14
[ 626-55-1 ]
[ 24424-99-5 ]
[ 658-24-2 ]
tert-butyl 5-(3-pyridinyl)-2,5-diazabicylo[2.2.2]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		2-5-Diazabicyclo[2.2.2]octane (390 mg, 3.5 mmole), prepared by the method of Sturm and Henry (J. Med. Chem. (1974), 17, 481), was treated with 3-bromopyridine (545 mg, 3.5 mmole), BINAP (92 mg, 0.14 mmole), Pd2(dba)3 (40 mg, 0.07 mmole) and sodium tert-butoxide (431 mg 4.5 mmole) in toluene (10 mL) under a nitrogen atmosphere. After heating the mixture at 75 C.5 C. for 2 hours, the mixture was allowed to cool to ambient temperature and treated with di-tert-butyl-dicarbonate (1.5 g, 6.9 mmole) and then allowed to stir an additional 16 hours. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, hexanes:ethyl acetate 9:1 to 1:1) to provide the title compound (193 mg, 19% yield). MS (DCI/NH3) m/z 290 (M+H)+, 307 (M+NH4)+.

Reference： [1]Patent: US2003/225268,2003,A1 .Location in patent: Page 29

15
[ 53533-54-3 ]
[ 658-24-2 ]
[ 864493-97-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 34 - 42

16
[ 14037-86-6 ]
[ 658-24-2 ]
C₃₂H₄₄N₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium carbonate; In N,N-dimethyl-formamide; for 48h;Inert atmosphere;	General procedure: Alkyl bromides (3 equivalents) were dissolved in 10 equivalents DMF (wt/v) and to this was added powdered K2CO3 (5 equivalents) and diamine. The mixture was stirred 2 d before addition of water which was rinsed several times with CH2Cl2, the combined CH2Cl2 was dried (MgSO4), filtered and chromatographed with MeOH saturated with NH3 in CH2Cl2 to isolate the product. Liquid products were dissolved in ether and precipitated out as white solids by the addition of 2M HCl/Ether.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5801 - 5804

17
2-bromobutyl 3,4,5-trimethoxybenzoate [ No CAS ]
[ 658-24-2 ]
C₃₄H₄₈N₂O₁₀*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%		General procedure: Alkyl bromides (3 equivalents) were dissolved in 10 equivalents DMF (wt/v) and to this was added powdered K2CO3 (5 equivalents) and diamine. The mixture was stirred 2 d before addition of water which was rinsed several times with CH2Cl2, the combined CH2Cl2 was dried (MgSO4), filtered and chromatographed with MeOH saturated with NH3 in CH2Cl2 to isolate the product. Liquid products were dissolved in ether and precipitated out as white solids by the addition of 2M HCl/Ether.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5801 - 5804

18
[ 54221-37-3 ]
[ 658-24-2 ]

Reference： [1]Patent: WO2008/134035,2008,A1

19
[ 54221-38-4 ]
[ 658-24-2 ]

Reference： [1]Patent: WO2008/134035,2008,A1

20
(2R,5S)-2,5-diaminohexanedioic acid diethyl ester dihydrochloride [ No CAS ]
[ 658-24-2 ]

Reference： [1]Patent: WO2008/134035,2008,A1

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[ CAS No. 658-24-2 ] {[proInfo.proName]}

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[ 658-24-2 ] Synthesis Path-Downstream 1~20

Precautionary Statements-General

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