[ CAS No. 234108-58-8 ] {[proInfo.proName]}

Name: 234108-58-8|tert-Butyl 4-(2-aminoethyl)-3-oxopiperazine-1-carboxylate|95%
Brand: Ambeed
SKU: A212632
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3d Animation Molecule Structure of 234108-58-8

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Quality Control of [ 234108-58-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 234108-58-8 ]

SDS Specification

Alternatived Products of [ 234108-58-8 ]

Product Details of [ 234108-58-8 ]

CAS No. :	234108-58-8	MDL No. :	MFCD28053710
Formula :	C₁₁H₂₁N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MCRRSQHTAKWRQS-UHFFFAOYSA-N
M.W :	243.30	Pubchem ID :	54065570
Synonyms :

Calculated chemistry of [ 234108-58-8 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	71.12
TPSA :	75.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	-0.53
Log Po/w (WLOGP) :	-0.74
Log Po/w (MLOGP) :	-0.19
Log Po/w (SILICOS-IT) :	-0.29
Consensus Log Po/w :	0.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.68
Solubility :	50.3 mg/ml ; 0.207 mol/l
Class :	Very soluble
Log S (Ali) :	-0.59
Solubility :	61.9 mg/ml ; 0.254 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.91
Solubility :	30.1 mg/ml ; 0.124 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.47

Safety of [ 234108-58-8 ]

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

Application In Synthesis of [ 234108-58-8 ]

* 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.

Upstream synthesis route of [ 234108-58-8 ]
Downstream synthetic route of [ 234108-58-8 ]

[ 234108-58-8 ] Synthesis Path-Upstream 1~2

1
[ 234108-59-9 ]
[ 234108-58-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With platinum(IV) oxide; palladium on activated charcoal; hydrogen In ethanol at 20℃;	step 2: A mixture of tert-butyl 4-(cyanomethyl)-3-oxopiperazine-1-carboxylate (3.0 g, 12.5 mmol), PtO₂(300 mg, 1.32 mmol) in EtOH (20 mL) was stirred at 20° C. under H₂(50 psi) overnight. The Pd/C catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to afford tert-butyl 4-(2-aminoethyl)-3-oxopiperazine-1-carboxylate (2.8 g, 93percent) as yellow solid. LCMS (ESI): m/z=244.2 [M+1]⁺.

Reference： [1] Patent: US2015/31674, 2015, A1, . Location in patent: Paragraph 0303; 0305; 0729
[2] Patent: US2004/102450, 2004, A1, . Location in patent: Page/Page column 90-91

2
[ 76003-29-7 ]
[ 234108-58-8 ]

Reference： [1] Patent: US2015/31674, 2015, A1,

[ 234108-58-8 ] Synthesis Path-Downstream 1~8

1
[ 14161-11-6 ]
[ 234108-58-8 ]
C₁₅H₂₁Cl₂N₅O₃ [ No CAS ]
C₁₅H₂₁Cl₂N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 120.0℃; for 3.0h;	EXAMPLE 95 1-[2-(Pyridazin-4-ylamino)-ethyl]-piperazin-2-one. 1-(2-Aminoethyl)-4-(tert-butyloxycarbonyl)-piperazin-2-one from EXAMPLE 92, Part A (1.0 g, 4.1 mmol) is treated with 3,4,5-trichloropyridazine (0.81 g, 4.1 mmol), triethylamine (0.57 ML, 4.1 mmol), THF (25 ML) and heated to 120 C. in a sealed tube for 3 hours.Upon cooling, the solution is diluted with ethyl acetate and washed with aqueous sodium bicarbonate (25 ML), water and dried over sodium sulfate.The organic layer is concentrated and chromatographed (5% methanol/methylene chloride) to give a mixture of isomers (0.8 g, 20 mmol).The mixture is dissolved in 0.5 M sodium methoxide in methanol (200 ML), treated with 10% Pd/C (0.5 g) and agitated under 50 PSI of hydrogen for 20 hours.The reaction mixture is filtered; the filtrate is concentrated to a residue which is chromatographed (NH4OH/H2O/MeOH/EtOAc, 1:1:2:90) to give crude 4-(tert-butyloxycarbonyl)-1-[2-(pyridazin-4-ylamino)-ethyl]-piperazin-2-one.This material is dissolved in a minimal amount of THF and treated with a saturated solution of HCl in ethyl acetate (50 ML).The solution is stirred at ambient temperature for 2 h and diluted with diethyl ether (50 ML).The precipitated title compoundcompound is collected and air dried (0.5 g, 1.7 mmol). MS m/z: 367, [M+1]+; 1H NMR (CD3OD, 300 MHz) delta8.8 (d, 1H), 8.5 (s, 1H), 7.4 (d, 1H), 4.1 (s, 2H), 3.5-3.8 (m, 8H).

Reference： [1]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 92

2
[ 234108-58-8 ]
[ 20928-46-5 ]
[ 234108-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In dichloromethane; for 5.0h;	B. 4-(tert-Butyloxycarbonyl)-1-[2-(2,3 5,6-tetrachloropyridin-4-ylamino)-ethyl]-piperazin-2-one. <strong>[234108-58-8]4-(tert-Butyloxycarbonyl)-1-(2-aminoethyl)-piperazin-2-one</strong> (4.0 g, 16 mmol) is dissolved in methylene chloride (150 ML) and treated with 4-nitro-2,3,5,6-tetrachloro-pyridine (4.8 g, 18 mmol) and N-methylmorpholine (4.0 ML, 36 mmol).The reaction mixture is stirred for 5 h, concentrated and the residue is purified by chromatography (50% ethyl acetate/hexane) to give the title compound (4.8 g, 10.5 mmol).Fab MS m/z: 457, 469, 461, [M+1]+; 1H NMR (CDCl3, 300 MHz) delta6.00 (t, 1H), 4.10 (s, 2H), 3.97 (m, 2H), 3.66 (m, 2H), 3.38 (m, 2H).

Reference： [1]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 91

3
[ 234108-59-9 ]
[ 234108-58-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With platinum(IV) oxide; palladium on activated charcoal; hydrogen; In ethanol; at 20.0℃; under 2585.81 Torr;	step 2: A mixture of tert-butyl 4-(cyanomethyl)-3-oxopiperazine-1-carboxylate (3.0 g, 12.5 mmol), PtO2 (300 mg, 1.32 mmol) in EtOH (20 mL) was stirred at 20 C. under H2 (50 psi) overnight. The Pd/C catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to afford tert-butyl 4-(2-aminoethyl)-3-oxopiperazine-1-carboxylate (2.8 g, 93%) as yellow solid. LCMS (ESI): m/z=244.2 [M+1]+.
	With hydrogen;platinum(IV) oxide; In ethanol; under 2585.81 Torr; for 24.0h;	A. 4-(tert-Butyloxycarbonyl)-1-(2-aminoethyl)-piperazin-2-one. 4-(tert-Butyloxycarbonyl)-piperazin-2-one (8.0 g, 40 mmol), EXAMPLE 40, is dissolved in THF (160 ML), cooled in an ice bath and treated with 60% sodium hydride (1.9 g, 48 mmol).The reaction mixture is stirred 40 minutes, then treated with tetra-butylammonium iodide (0.35 g, 0.95 mmol) and bromoacetonitrile (3.4 ML, 48 mmol).After 2 h the reaction is quenched with water, concentrated to a small volume and extracted with methylene chloride (3*).The combined organic extracts are concentrated and the residue is chromatographed (50% ethyl acetate/hexane) to give 4-(tert-butyloxycarbonyl)-1-cyanomethyl-piperazin-2-one (5.2 g, 21.7 mmol).This material is dissolved in ethanol (140 ML) and treated with platinum oxide (0.83 g) at 50 PSI of hydrogen gas for 24 hours.The catalyst is removed by filtration and the solution is concentrated to yield 4-(tert-butyloxycarbonyl)-1-(2-aminoethyl)-piperazin-2-one (5.2 g, 21.6 mmol).1H NMR (CDCl3, 300 MHz) delta4.08 (s, 2H), 3.62 (m, 2H), 3.44 (t, 2H), 3.38 (t, 2H), 2.89 (t, 2H).

Reference： [1]Patent: US2015/31674,2015,A1 .Location in patent: Paragraph 0303; 0305; 0729
[2]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 90-91

4
[ 76003-29-7 ]
[ 234108-58-8 ]

Reference： [1]Patent: US2015/31674,2015,A1
[2]Patent: WO2019/183577,2019,A1

5
[ 3261-87-8 ]
[ 234108-58-8 ]
2-((2-((2-(4-(tert-butoxycarbonyl)-2-oxopiperazin-1-yl)ethyl)amino)-2-oxoethyl)thio)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54 mg	In tetrahydrofuran; for 0.0833333h;	A solution of /er/-butyl 4-(2-aminoethyl)-3-oxopiperazine- l-carboxylate, 1-324 (crude product, ca. 0.77 mmol) and 1,4 - thiodiglycolic anhydride (100 mg, 1.0 equiv.) in THF (5 mL) was stirred for 5 min and concentrated under reduced pressure. The crude product was purified by preparative HPLC (Mobile Phase: MeCN/ThO (0.1% formic acid), Gradient:20-30% MeCN) to afford carboxylic acid 1-325 as a white solid (54 mg, 19 % yield). MS (ESI, pos. ion) m/z: 398.2 (M+23). 1H NMR (400 MHz, CDC13) d 4.14 (s, 2H), 3.67 (dd, 4H), 3.59 - 3.50 (m, 2H), 3.44 (d, 2H), 3.35 (s, 2H), 3.27 (s, 2H), 1.47 (s, 9H).

Reference： [1]Patent: WO2019/183577,2019,A1 .Location in patent: Page/Page column 246-248

6
[ 786683-69-0 ]
[ 234108-58-8 ]

Reference： [1]Patent: WO2019/183577,2019,A1

7
[ 910573-06-7 ]
[ 234108-58-8 ]

Reference： [1]Patent: WO2019/183577,2019,A1

8
tert-butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-3-oxopiperazine-1-carboxylate [ No CAS ]
[ 234108-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In methanol; at 20.0℃; for 18.0h;Cooling with ice;	To a solution of /cvV-butyl 4-(2-(l,3-dioxoisoindolin-2-yl)ethyl)-3-oxopiperazine- (1905) 1 -carboxylate, 1-323 (0.58 g, ca. 0.77 mmol) in MeOH (8 mL) that had been pre-cooled in an ice-water bath was added NH2NH2 (85% in LEO, 0.1 mL, 2 equiv.). The reaction mixture was allowed to warm to ambient temperature and then stirred for 18 hours. Upon completion of the reaction, the slurry was filtered and the filtrate was concentrated to afford a pale oil. The crude product, 1-324 was used directly for next step. MS (ESI, pos. ion) m/z: 266(M+23).

Reference： [1]Patent: WO2019/183577,2019,A1 .Location in patent: Page/Page column 246-247

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Ghs Precautionary Statements

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 234108-58-8 ] {[proInfo.proName]}

Quality Control of [ 234108-58-8 ]

Related Doc. of [ 234108-58-8 ]

Product Details of [ 234108-58-8 ]

Calculated chemistry of [ 234108-58-8 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 234108-58-8 ]

[ 234108-58-8 ] Synthesis Path-Upstream 1~2

[ 234108-58-8 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 234108-58-8 ]

Amides

Amines

Related Parent Nucleus of [ 234108-58-8 ]

Aliphatic Heterocycles

Piperazines

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[ 234108-58-8 ]

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[ 234108-58-8 ]