[ CAS No. 1240586-48-4 ]

Name: 1240586-48-4|(2R,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate|95%
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SKU: A259658
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Quality Control of [ 1240586-48-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1240586-48-4 ]

Product Details of [ 1240586-48-4 ]

CAS No. :	1240586-48-4	MDL No. :	MFCD08686669
Formula :	C₁₁H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PGZCVLUQTJRRAA-RKDXNWHRSA-N
M.W :	214.30 g/mol	Pubchem ID :	44828681
Synonyms :

Calculated chemistry of [ 1240586-48-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.12
TPSA :	41.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.89
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.69
Consensus Log Po/w :	1.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.8
Solubility :	3.38 mg/ml ; 0.0158 mol/l
Class :	Very soluble
Log S (Ali) :	-1.79
Solubility :	3.44 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.6
Solubility :	5.42 mg/ml ; 0.0253 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.08

Safety of [ 1240586-48-4 ]

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

Application In Synthesis of [ 1240586-48-4 ]

* 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 [ 1240586-48-4 ]

[ 1240586-48-4 ] Synthesis Path-Downstream 1~6

1
[ 194032-16-1 ]
[ 1240586-48-4 ]
[ 194031-90-8 ]

Yield	Reaction Conditions	Operation in experiment
		23 Cis-2,5-Dimethyl-1-[(4-methyl-5-isoquinolinyl)sulfonyl]piperazine dihydrochloride EXAMPLE 23 Cis-2,5-Dimethyl-1-[(4-methyl-5-isoquinolinyl)sulfonyl]piperazine dihydrochloride Using 0.43 g of cis-1-(tert-butoxycarbonyl)-2,5-dimethylpiperazine and 0.48 g of 5-chlorosulfonyl-4-methylisoquinoline, the procedure of Example 1 was otherwise repeated to provide 0.2 g of the objective compound (white crystals). m.p. 258-263° C. (decomp.) Elemental analysis (for C16 H21 N3 O2 S.2HCl) Calcd. (%): C, 48.98; H, 5.91; N, 10.71 Found (%): C, 48.69; H, 6.15; N, 10.61

Reference： [1]Current Patent Assignee: D.WESTERN THERAPEUTICS INSTITUTE INC - US6153608, 2000, A

2
[ 1033711-56-6 ]
[ 24424-99-5 ]
[ 1240586-48-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In methanol	A A. Compound 12 and Intermediates (2R,5R)-1-tert-butoxycarbonyl-2,5-dimethylpiperazine (19) A solution of 1.43 g (5.19 mmol) of (2R,5R)-2,5-dimethyl piperazine dihydrobromide 181 was dissolved in 30 mL of MeOH along with 262 mg (2.59 mmol) of Et3N. Into this solution was added 565 mg (2.59 mmol) of Boc2O and the solution was stirred overnight. The solution was subjected to rotary evaporation and added 20 mL of CH2Cl2 and 20 ml of conc. NaHCO3. The mixture was shaken thoroughly and the layers separated. The organic layer was extracted twice with conc. NaHCO3 and the organic layer dried over MgSO4, filtered and the solvents removed. The residue was purified by silica-gel column chromatography eluting with 2:1 CMA80:CH2Cl2 to yield 497 mg (84%) of pure 19 as a clear oil. 1H NMR (CDCl3): δ 4.28-4.02 (bd, 1H); 3.90-3.63 (bdd, 1H); 2.99-2.94 (dd, 1H); 2.81-2.75 (d, 1H); 2.71-2.62 (m, 1H); 2.53-2.49 (d, 6H); 1.25 (d, 3H); 1.06 (d, 3H). ESIMS: m/z 215 (M+H+, 100).

Reference： [1]Current Patent Assignee: RESEARCH TRIANGLE INSTITUTE - US2012/295919, 2012, A1 Location in patent: Page/Page column 14

3
[ 1240586-48-4 ]
[ 350-46-9 ]
[ 1799562-43-8 ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 168h; Inert atmosphere;	79.1 (2R,5R)-tert-butyl 2,5-dimethyl-4-(4- nitrophenyl)piperazine-1-carboxylate: A suspension of 1-fluoro-4-nitrobenzene (329 mg, 2.333mmol), (2R,5R)-tert-butyl 2,5-dimethylpiperazine-1- carboxylate (500 mg, 2.333 mmol) and potassium carbonate (484 mg, 3.50 mmol) in anhydrous DMF (2 mL) was heated to50 °C under a nitrogen atmosphere for 7 days. Thereaction mixture was allowed to cool to room temperature,diluted with water (70 mL) and stirred at roomtemperature for 15 minutes. The mixture was extractedinto ethyl acetate (3 x 20 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue was purified by two consecutive Biotage chromatography columns (silica lOOg cartridge,cyclohexane:ethyl acetate, gradient elution from 90:10 to50:50) to give the title compound as a yellow solid (200 mg, 26%). ‘H NMR (400 MHz, CDC13) : 3 8.11 (d, 2H), 6.66 (d, 2H), 3.93-4.21 (m, 3H), 3.79 (dd, 1H), 3.08 (dd, 1H), 2.90 (dd, 1H), 1.41 (s, 9H), 1.20 (dd, 6H) . LCMS (MethodC): = 1.74 mi m/z = 336 [M+H].

Reference： [1]Current Patent Assignee: THE MCCLAY FOUNDATION - WO2015/92431, 2015, A1 Location in patent: Page/Page column 188; 189

4
[ 1240586-48-4 ]
[ 350-46-9 ]
[ 1799562-44-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 168 h / 50 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 50 °C

Reference： [1]Current Patent Assignee: THE MCCLAY FOUNDATION - WO2015/92431, 2015, A1

5
(2R,5R)-tert-butyl 2,5-dimethylpiperazine-1-carboxylate [ No CAS ]
[ 27064-94-4 ]
tert-butyl (2R,5R)-4-(bis(4-fluorophenyl)methyl)-2,5-dimethylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.2%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃;	INTERMEDIATE 93 (1097) tert-butyl (2R,5R)-4-(bis(4-fluorophenyl)methyl)-2,5-dimethylpiperazine-1-carboxylate To a solution of 4,4'-(chloromethylene)bis(fluorobenzene) (130 mg, 0.545 mmol) in acetonitrile (20 mL) at room temperature were added tert-butyl (2R,5R)-2,5- dimethylpiperazine-1-carboxylate (128 mg, 0.599 mmol) and DIPEA (0.285 mL, 1.634 mmol). The reaction mixture was heated to 80 °C overnight. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in DCM and washed with water, brine and dried over sodium sulfate and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using 24 g flash column, eluting with 30 % EtOAc in petroleum ether. The fractions were concentrated under reduced pressure to yield tert-butyl (2R,5R)-4-(bis(4-fluorophenyl)methyl)-2,5- dimethylpiperazine-1-carboxylate (150 mg, 58.2 % yield); LCMS: m/z = 417.4 (M+H); rt 1.72 min. LCMS Method: M. phase A:10 mM ammonium acetate:acetonitrile (95:5) Mobile phase B:10 mM ammonium acetate:acetonitrile (5:95) Method:%B: 0 min-20:2 min-100: 2.3 min-100 Flow: 0.7 mL/min Column: AQUITY UPLC BEH C18 (3.0 x 50 mm) 1.7 ^m.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/6018, 2020, A1 Location in patent: Page/Page column 275; 276

6
[ 1240586-48-4 ]
[ 2446932-17-6 ]
[ 2446932-90-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 16h;	31 A. tert-Butyl (2R,5R)-4-(2-(4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5- dimethyl-4-oxo-2-thioxoimidazolidin-l-yl)-2-ethylphenoxy)ethyl)-2,5-dimethylpiperazine-l- carboxylate. 4-(3-(4-(2-Bromoethoxy)-3-ethylphenyl)-4,4-dimethyl-5-oxo-2- thioxoimidazolidin-l-yl)-2-(trifluoromethyl)benzonitrile (0.200 g, 0.370 mmol) (prepared as described herein), (2R,5R)-tert-butyl 2,5-dimethylpiperazine-l-carboxylate (0.095 g, 0.444 mmol) and DIEA (0.162 mL, 0.925 mmol) were combined in DMF (1.5 mL) and the mixture was heated to 70 °C in a screw cap vial. After 16 h, the solution was concentrated under reduced pressure to afford an orange residue that was purified by silica gel column chromatography (0-80% EtOAc in hexanes) to afford the title compound (0.204 g, 0.299 mmol, 81.0% yield). MS (ESI) m/z 674 [M+l]+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/132014, 2020, A1 Location in patent: Paragraph 00499

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P262	Do not get in eyes, on skin, or on clothing.
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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
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Physical hazards
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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. 1240586-48-4 ]

Quality Control of [ 1240586-48-4 ]

Related Doc. of [ 1240586-48-4 ]

Product Details of [ 1240586-48-4 ]

Calculated chemistry of [ 1240586-48-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1240586-48-4 ]

Application In Synthesis of [ 1240586-48-4 ]

[ 1240586-48-4 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 1240586-48-4 ]

Amides

Related Parent Nucleus of [ 1240586-48-4 ]

Aliphatic Heterocycles

Piperazines

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Prevention

Response

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Physical hazards

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Environmental hazards

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Related Functional Groups of
[ 1240586-48-4 ]

Related Parent Nucleus of
[ 1240586-48-4 ]