[ CAS No. 325145-35-5 ] {[proInfo.proName]}

Name: 325145-35-5|(S)-tert-Butyl 2-ethylpiperazine-1-carboxylate|97%
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SKU: A147913
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Quality Control of [ 325145-35-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 325145-35-5 ]

Product Details of [ 325145-35-5 ]

CAS No. :	325145-35-5	MDL No. :	MFCD07772100
Formula :	C₁₁H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CTCGRXDGXGUOTE-VIFPVBQESA-N
M.W :	214.31	Pubchem ID :	17750462
Synonyms :

Calculated chemistry of [ 325145-35-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	4
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) :	-6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.82
Log Po/w (XLOGP3) :	1.42
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.97
Consensus Log Po/w :	1.44

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 :	3.4 mg/ml ; 0.0159 mol/l
Class :	Very soluble
Log S (Ali) :	-1.9
Solubility :	2.71 mg/ml ; 0.0127 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.84
Solubility :	3.06 mg/ml ; 0.0143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.75

Safety of [ 325145-35-5 ]

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

Application In Synthesis of [ 325145-35-5 ]

* 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 [ 325145-35-5 ]
Downstream synthetic route of [ 325145-35-5 ]

[ 325145-35-5 ] Synthesis Path-Upstream 1~5

1
[ 502482-44-2 ]
[ 325145-35-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 7, p. 1345 - 1348
[2] Patent: WO2006/56752, 2006, A1, . Location in patent: Page/Page column 67
[3] Patent: US2008/255150, 2008, A1, . Location in patent: Page/Page column 20

2
[ 24424-99-5 ]
[ 325145-35-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 7, p. 1345 - 1348

3
[ 324750-04-1 ]
[ 325145-35-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 7, p. 1345 - 1348

4
[ 325145-36-6 ]
[ 325145-35-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 7, p. 1345 - 1348

5
[ 110-85-0 ]
[ 110-17-8 ]
[ 325145-35-5 ]

Reference： [1] Patent: US6638936, 2003, B1,

[ 325145-35-5 ] Synthesis Path-Downstream 1~32

1
[ 502482-44-2 ]
[ 325145-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 2850.29 Torr; for 16h;	A solution of the product from example 69 part c) (6.09 g) and 10percent Pd/C (1.14 g) in EtOH (85 mL) was hydrogenated at 3.8 bar for 16 h. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give the sub-title compound as an oil (3.65 g).1H NMR (CDCl3) delta 3.87 (2H, m), 2.87 (4H, m), 2.68 (IH, td), 1.76 (IH, m), 1.59 (IH, m), 1.46 (9H, s), 0.89 (3H, t).
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 2850.29 Torr; for 16h;	A solution of the product from example 69 part c) (6.09 g) and 10percent Pd/C (1.14 g) in EtOH (85 mL) was hydrogenated at 3.8 bar for 16 h. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give the sub-title compound as an oil (3.65 g).1H NMR (CDCl3) delta 3.87 (2H, m), 2.87 (4H, m), 2.68 (1H, td), 1.76 (1H, m), 1.59 (1H, m), 1.46 (9H, s), 0.89 (3H, t).

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348
[2]Patent: WO2006/56752,2006,A1 .Location in patent: Page/Page column 67
[3]Patent: US2008/255150,2008,A1 .Location in patent: Page/Page column 20

2
[ 325145-35-5 ]
[ 603-79-2 ]
(S)-4-(2,3-Dimethyl-benzoyl)-2-ethyl-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

3
[ 1359649-44-7 ]
[ 325145-35-5 ]
[ 950848-57-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 88h;	Boc-2-S-ethyl piperazine 22 (prepared as per Kiley et al Org. Prep. Proc- Int. 1990, 22, 761 ; 4.2 g, 18.6 mmol), tris(dibenzylideneacetone)dipalladium (340 mg, 0.37 mmol), racemic-2,2'-bis(diphenylphosphino)-1 ,1'-binaphthyl (BINAP) (495 mtf, 0.74 mmol), cesium carbonate (12 g, 37.2 mmol) and toluene (80 ml). After the mixture was heated at 100 0C for 16 h, fresh tris(dibenzylideneacetone)- dipalladium (340 mg, 0.37 mmol) and BINAP (495 mg, 0.74 mmol) were added and the heating was continued for 3 days. The solvent was removed in vacuo, and the residue was suspended in a 100 ml portion of ethyl acetate. This mixture was extracted with water and brine. The separated organic layer was dried over sodium sulfate and concentrated in vacuo. Purification of the residue via silica gel flash chromatography (5percent methanol/ 95percent DCM) yielded 5.3 g of a partially purified material 23 which was used directly in the next step. M.S. M+H = 350

Reference： [1]Patent: WO2007/109238,2007,A1 .Location in patent: Page/Page column 83

4
[ 950848-56-3 ]
[ 325145-35-5 ]
[ 950848-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 88h;	Example 2J kJlBOCA 250 ml round bottom flask was charged with A2 (4g, 15.9 mmol), 1-Boc-2-S-ethyl piperazine A3 (prepared as per Kiley et al Org. Prep. Proc. Int. 1990, 22, 761; 4.2 g, 18.6 mmol), tris(dibenzylideneacetone)dipalladium , (340 mg, 0.37 mmol), racemic-2,2'-bis(diphenylphosphino)-1 ,1'-binaphthyl (BINAP) (495 mg, 0.74 mmol), cesium carbonate (12g, 37.2 mmol) and toluene (80 ml). After the mixture was heated at 1003C for 16 h, fresh tris(dibenzylidene- acetone)dipalladium (340 mg, 0.37 mmol) and BINAP (495 mg, 0.74 mmol) were added and the heating was continued for 3 days. The solvent was removed in vacuo, and the residue was suspended in a 100 ml portion of ethyl acetate. This mixture was extracted with water and brine, dried over sodium sulfate, and concentrated in vacuo. Purification of the residue via silica gel flash chromatography (5percentmethanol/ 95percent DCM) yielded 5.3 g of a partially purified material which was used directly in the next step. M+H = 350

Reference： [1]Patent: WO2008/8453,2008,A1 .Location in patent: Page/Page column 65

5
[ 24424-99-5 ]
[ 325145-35-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

6
[ 325145-35-5 ]
(2,3-Dimethyl-phenyl)-((S)-3-ethyl-piperazin-1-yl)-methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

7
[ 325145-35-5 ]
[(S)-4-((R)-2-Amino-3-mercapto-propyl)-3-ethyl-piperazin-1-yl]-(2,3-dimethyl-phenyl)-methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

8
[ 325145-35-5 ]
{(R)-1-[(S)-4-(2,3-Dimethyl-benzoyl)-2-ethyl-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

9
[ 324750-04-1 ]
[ 325145-35-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

10
[ 325145-36-6 ]
[ 325145-35-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

11
[Benzyl-((S)-2-tert-butoxycarbonylamino-butyryl)-amino]-acetic acid ethyl ester [ No CAS ]
[ 325145-35-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1345 - 1348

13
[ 888972-26-7 ]
[ 325145-35-5 ]
[ 888972-60-9 ]

Yield	Reaction Conditions	Operation in experiment
		The product from example 69 part d) (1 g), the product from example 13 part b) (1.263 s g) and MgSO4 (xs) were stirred in THF (50 ml) for 16 h. Sodium triacetoxy borohydride (3.96 g) was added and the reaction stirred for 16 h. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated in vacuo. It was purified by chromatography (silica, (20percent EtOAc/isohexane as eluent)), to give the sub-titled compound as a colourless oil (2.03 g). o MS: APCI (+ve): 469 (M+l)

Reference： [1]Patent: WO2006/56752,2006,A1 .Location in patent: Page/Page column 68

14
[ 110-85-0 ]
[ 110-17-8 ]
[ 325145-35-5 ]

Yield	Reaction Conditions	Operation in experiment
1.39 g (81%)	In diethyl ether; ethanol;	This piperazine was dissolved in 20 mL absolute ethanol and the solution was filtered. The filtrate was heated to reflux and treated with 0.48 gm fumaric acid. The mixture was heated for five minutes until all the solids dissolved. The solution was concentrated under reduced pressure and the residue was triturated with 50 mL diethyl ether. The slurry was allowed to stir for 0.5 hour, was filtered, and the white solid was rinsed with 2*20 mL diethyl ether. The solid was dried at 60° C. under reduced pressure for 4 hours to provide 1.39 g (81percent) of the title compound. mp=163-164.5° C. EA: Calculated for C15H17F3N2O.C4H4O4: C, 55.07; H, 5.11; N, 6.76. Found: C, 54.98; H, 5.09; N, 6.77.

Reference： [1]Patent: US6638936,2003,B1

15
[ 286836-99-5 ]
[ 325145-35-5 ]
[ 325145-41-3 ]

Yield	Reaction Conditions	Operation in experiment
		1-(4-trifluoromethylbenzofur-7-yl)-3(S)-ethyl-4-tert-butoxycarbonylpiperazine Beginning with 1.45 gm (5.47 mMol) 4-trifluoromethyl-7-bromobenzofuran and 1.4 gm (6.53 mMol) 1-(tert-butoxycarbonyl)-2(S)-ethylpiperazine, 1.82 gm (84percent) of the desired compound were prepared essentially as described in Example 1. ESMS: m/e=399 (M+1)

Reference： [1]Patent: US6638936,2003,B1

16
[ 325145-35-5 ]
2-(S)-ethylpiperazine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 0.333333h;	Concentrated hydrochloric acid (3 ml) was added to 2-(S)-ethyl-1-tert-butoxycarbonylpiperazine (986 mg, 4.27 mmol) and the resulting mixture was stirred for 20 minutes and then concentrated under reduced pressure, and the solvent was removed azeotropically with ethanol. The resulting solid was washed with 2-propanol to give the title compound (694 mg) as a colorless solid. This compound was used in the next step without being purified.

Reference： [1]Patent: US2010/130492,2010,A1 .Location in patent: Page/Page column 132

17
[ 155937-28-3 ]
[ 325145-35-5 ]
[ 1228022-22-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 24h;	Preparation 7(S)-tert-Butyl 2-ethyl-4-(4-(4-fluorophenyl)phthalazin-1-yl)piperazine-1-carboxylateHeat a mixture of 1-chloro-4-(4-fluorophenyl)phthalazine (5.02 g, 19.4 mmol), <strong>[325145-35-5](S)-tert-butyl 2-ethylpiperazine-1-carboxylate</strong> (5.00 g, 23.3 mmol) and K2CO3 (5.38 g, 38.9 mmol) in DMSO (75 mL) at 120° C. for 1 d.Pour the reaction mixture into water, rinsing with EtOAc.Extract with EtOAc.Wash the organic layer with water (2*), then brine, dry over Na2SO4, and concentrate under reduced pressure.Purify the resulting residue by flash silica gel chromatography (gradient of 20 to 80percent EtOAc in hexanes) to provide the title compound (5.11 g, 60percent). ES/MS m/z 437.2 (M+1).

Reference： [1]Patent: US2011/190304,2011,A1 .Location in patent: Page/Page column 6

18
[ 1175014-68-2 ]
[ 325145-35-5 ]
C₂₅H₂₉ClN₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5480 - 5486

19
trans-4-(4-fluorophenoxy)-N-(4-formyl-3-methylphenyl)-N-methylcyclohexanecarboxamide [ No CAS ]
[ 325145-35-5 ]
tert-butyl (2S)-4-{4-[[trans-4-(4-fluorophenoxy)cyclohexyl]carbonyl}(methyl)amino]-2-methylbenzyl}-2-ethylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	(8D) Tert-butyl (2S)-4-{4-[[trans-4-(4-fluorophenoxy)cyclohexyl]carbonyl}(methyl)amino]-2-methylbenzyl}-2-ethylpiperazine-1--carboxylate [0230] Trans-4-(4-fluorophenoxy)-N-(4-formyl-3-methylphenyl)-N-methylcyclohexanecarboxamide (55.0 mg, 0.149 mmol) produced in (8C) and <strong>[325145-35-5]tert-butyl (2S)-2-ethylpiperazine-1-carboxylate</strong> (39.0 mg, 0.182 mmol) were dissolved in dichloromethane (3 mL), and acetic acid (45.0 mg, 0.749 mmol) was added thereto at room temperature, and then, sodium triacetoxy borohydride (48 mg, 0.226 mmol) was added thereto at 0°C. Then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. [0231] To the reaction solution, a saturated aqueous solution of sodium hydrogen carbonate was added, and the organic matter was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate = 100:0 to 0:100 (v/v)), whereby the target compound was obtained as a colorless oil (70.0 mg, yield: 83percent). 1H-NMR (CDCl3, 400MHz): delta0.78 (3H, t, J = 7.6 Hz), 1.19-1.05 (2H, m), 1.46 (9H, s), 1.82-1.58 (6H, m), 2.16-2.02 (4H, m), 2.28-2.18 (1H, m), 2.38 (3H, s), 2.77-2.64 (2H, m), 3.08-2.96 (1H, m), 3.23 (3H, s), 3.48-3.35 (2H, m), 4.13-3.82 (3H, m), 6.80-6.74 (2H, m), 6.98-6.88 (4H, m), 7.29 (1H, d, J = 7.4 Hz).

Reference： [1]Patent: EP2623492,2013,A1 .Location in patent: Paragraph 0230-0231

20
[ 1133116-39-8 ]
[ 325145-35-5 ]
[ 1509949-08-9 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 10132 - 10141

21
[ 906559-30-6 ]
[ 325145-35-5 ]
C₁₉H₂₉ClN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	Chloride 3 (5.35 g, 24.4 mmol) was dissolved in DMF (50 mL, dried over molsieves). Piperazine 4 (5.0 g, 23.3 mmol) was added, followed by the addition of K2CO3 (8.0 gr, 58 mmol). The mixture was stirred overnight at 80°C. The DMF was evaporated under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give crude Boc-protected product. This was dissolved in DCM (50 mL) and CF3COOH (5 mL) was added dropwise. The mixture was stirred for 1 hour at room temperature and subsequently concentrated under vacuum. The residue was dissolved in DCM (25 mL) and washed with 1.0M aq. NaOH (25 mL) and water (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. Column chromatography (gradient: EtOAc/Et3N 99/1 toEtOAc/MeOH/Et3N 80/20/1) afforded the product as a white solid (3.35 g, 46 percent).LC-MS purity: 98+ percent. 1H-NMR (CDCl3, 400 MHz) delta 8.48 (d, 1H, J=2.1 Hz), 7.97 (d, 1H, J=2.1Hz), 6.09 (br t, 1H), 4.00-3.89 (m, 2H), 3.48 (dq, 2H, J1=7.3 Hz), 3.11-2.89 (m, 3H), 2.82-2.72(m, 1H), 2.58 (dd, 1H, J1=12.4 Hz, J2=10.0 Hz), 1.52-1.35 (m, 2H), 1.23 (t, 3H, J=7.3 Hz),0.97 (t, 3H, J=7.5 Hz).

Reference： [1]Molecular Pharmacology,2014,vol. 85,p. 116 - 126

22
C₁₆H₁₅N₃O₃ [ No CAS ]
[ 325145-35-5 ]
C₂₇H₃₅N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	ER-895473 (103 mg, 0.261 mmol, 27.1percent yield) was prepared in a similar manner to ER-899742 starting with 38 (286 mg, 0.962 mmol) and <strong>[325145-35-5](S)-tert-butyl 2-ethylpiperazine-1-carboxylate</strong> (206 mg, 0.962 mmol). DMF (3 mL) was used instead of DCM for the amide forming reaction and 2.0 M HCl in ethyl ether (1.3 mL, 2.6 mmol) was used in the Boc-deprotection process using acetonitrile (1 mL) as a solvent. ER-895473 was purified by reverse-phase HPLC (X-Bridge C18 19×100 mm column; eluting with a gradient of increasing acetonitrile in water containing 0.1percent formic acid). The product fractions were combined and concentrated to dry followed by dilution in MeOH (1 mL), passed through as basic silica gel plug (Biotage SiCO3, 1 g, eluting with MeOH (1 mL)), concentrated and dried in vacuo.To a stirred solution of 38 (300 mg, 1.01 mmol) in DCM (2 mL) was added the mixture of (3S,4R)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate and (3R,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate, 77 (205.3 mg, 1.005 mmol), HBTU (247 mg, 1.211 mmol) and DIEA (0.70 mL, 4.04 mmol) followed by stifling at rt for 16 h. The was found complete and concentrated to dryness followed by dissolving in EtOAc (20 mL), washed 1 time with water (10 mL), 2 N citric acid in water (10 mL), saturated NaHCO3 (10 mL), and brine (10 mL). The combined aqueous layers were extracted 3 times with EtOAc (10 mL ea.) after which time the combined organic fractions were dried over MgSO4, filtered and concentrated to dry. The crude product was purified over a 25 g Biotage silica gel column eluting with 0-10percent MeOH in DCM (200 mL total) to provide the diastereomeric mixture of 78 and 79.

Reference： [1]Patent: US2015/105370,2015,A1 .Location in patent: Paragraph 0444; 0458

23
((2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl)methyl 4-methylbenzenesulfonate [ No CAS ]
[ 325145-35-5 ]
5-((2S,6R)-2-(((S)-4-(3,3-dimethylbutanoyl)-3-ethylpiperazin-1-yl)methyl)-6-methylmorpholino)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In N,N-dimethyl acetamide; at 110℃; for 12h;	Compound 15 as Boc-Protected ER-890963 To a solution of 14 (13.9 g, 31.77 mmol) and TEA (8.86 mL, 63.541 mmol) in DMA (89 mL) at rt was added dropwise commercially available <strong>[325145-35-5](S)-tert-butyl 2-ethylpiperazine-1-carboxylate</strong> (7.49 g, 34.95 mmol) over 5-min period. The reaction mixture was stirred at 110° C. for 12 h to completion after which time the reaction was cooled to rt. The reaction was concentrated to remove DMA followed by dilution with DCM (30 mL). The resultant organic solution was washed two times with water (30 mL each), brine (30 mL), and dried over MgSO4. The crude was filtered, concentrated in vacuo, and purified over silica gel (SNAP 340 g eluting 10percent to 30percent EtOAc in heptene, TLC heptane/EtOAc=3/1, rt=0.6) gave 5-((2S,6R)-2-(((S)-4-(3,3-dimethylbutanoyl)-3-ethylpiperazin-1-yl)methyl)-6-methylmorpholino)quinoline-8-carbonitrile or Boc-protected ER-890963 (12.27 g, 24.15 mmol, 76percent yield) as yellow powder after concentration of the combined desired fractions and drying in vacuo.

Reference： [1]Patent: US2015/105370,2015,A1 .Location in patent: Paragraph 0204

24
5-chloro-1-(chloromethyl)-2-methyl-3-nitrobenzene [ No CAS ]
[ 325145-35-5 ]
(S)-4-(5-chloro-2-methyl-3-nitrobenzyl)-2-ethylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.3 g	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;	To a solution of 5-chloro-1- (chloromethyl) -2-methyl-3-nitrobenzene (D23 1.232 g) in DMF (20 mL) were added (S) -tert-butyl 2-ethylpiperazine-1-carboxylate (1 g) and K2CO3(1.935 g) at 60. After stirring overnight the mixture was poured into ice/water and then extracted with DCM (3×100 mL) . The combined organic layers were dried over Na2SO4 filtered and concentrated to give a yellow oil which was purified by column chromatography (eluting with EAPE5) to give the title compund (1.3 g) as a yellow solid. MS (ESI) C19H28ClN3O4requires 397 found 398 [M+H]+.
3 g	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;	At 60 ° C (S) chloro-1- (chloromethyl) -2-methyl-3-nitrobenzene (D23, 1.232 g) in DMF (20 mL) was added <strong>[325145-35-5](S)-2-ethylpiperazine-1-carboxylic acid tert-butyl ester</strong>(1 g) and K2CO3 (1.935 g). After taking a over night, The mixture is poured into ice / water,Then extracted with DCM (3 x 100 mL).The combined organic layers were dehydrated by Na2S04,Filter & apos; with concentrated to produce a yellow oil,Purification by column chromatography (using EpsilonAlpha: PE = 5percent) gave the title compound ( 3 g) as a yellow solid

Reference： [1]Patent: WO2015/180614,2015,A1 .Location in patent: Page/Page column 29-30
[2]Patent: TW2017/14884,2017,A .Location in patent: Paragraph 0090

25
[ 1399119-66-4 ]
[ 325145-35-5 ]
(S)-2-ethyl-4-(5-((2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)-2-fluorobenzoyl)piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.8%		The 3 - ((2,4-dioxo -3,4-dihydrochinazolines having antiviral properties -1 (2H)-yl) methyl) benzoic acid (150 mg, 0 . 51mmol), HATU (388 mg, 1 . 02mmol), HOBt (138 mg, 1 . 02mmol) and TEA (104 mg, 1 . 02mmol) into the reaction bottle in, addition of about 5 ml of the dissolution of water-free DMF, r.t. The lower stirring 15 min, then dropwise (S)-N-Boc-2-ethyl piperazine (153 mg, 0 . 76mmol) in the DMF solution to the reaction solution, r.t. The lower stirring sleepovers, reducing pressure and evaporating solvent, addition of about 20mLDCM, saturated NaHCO3washing (25 ml × 2), dried anhydrous sodium sulfate, silica gel column chromatography to obtain 150 mg of solid, yield 65.8percent.

Reference： [1]Patent: CN105461697,2016,A .Location in patent: Paragraph 0142; 0143; 0144; 0145; 0146

26
2-carboxyl-1H-benzo[d]immidazole-4-carboxamide [ No CAS ]
[ 325145-35-5 ]
(S)-tert-butyl 4-(4-carbamoyl-1H-benzo[d]imidazole-2-carbonyl)-2-ethylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.6%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 20h;	General procedure: A mixture of 2-carboxyl-1H-benzo[d]immidazole-4-carboxamide (75 mg, 0.37 mmol), EDC (210 mg, 1.09 mmol), HOBt(147 mg, 1.09 mmol), Et3N (0.4 mL, 2.93 mmol) and N-Boc-aminopyrrolidine(202 mg, 1.09 mmol) in DMF (5 mL) was stirred atroom temperature for 20 h and then H2O was added to the mixture.The solutionwas extracted with the solvent mixture (ethyl acetate/methanol = 10:1) (30 mL x 3) and then the organic layer waswashed with brine (20 mL x 2). The combined organic layer wasdried over anhydrous MgSO4. After filtration and concentration, thecrude product was obtained and purified with column chromatography(methylene chloride/methanol 50:1 to 40:1) to givecompound 7a as a white solid (74 mg, 54.4percent).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 132,p. 26 - 41

27
[ 325145-35-5 ]
[ 179232-29-2 ]
tert-butyl (2S)-2-ethyl-4-(3-fluoro-4-methoxycarbonylphenyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4444 - 4457

28
[ 325145-35-5 ]
tert-butyl (2S)-4-(4-carbamoyl-3-fluorophenyl)-2-ethylpiperazine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4444 - 4457

29
[ 325145-35-5 ]
C₂₅H₃₁FN₆O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4444 - 4457

30
[ 325145-35-5 ]
4-[(3S)-3-ethylpiperazin-1-yl]-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4444 - 4457

31
[ 325145-35-5 ]
C₁₈H₂₅FN₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4444 - 4457

32
[ 325145-35-5 ]
C₂₁H₂₇FN₄O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4444 - 4457

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P230	Keep wetted
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P233	Keep container tightly closed.
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P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
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.
P403 + P235	Store in a well-ventilated place. Keep cool.
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.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 325145-35-5 ] {[proInfo.proName]}

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Medicinal Chemistry

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[ 325145-35-5 ] Synthesis Path-Upstream 1~5

[ 325145-35-5 ] Synthesis Path-Downstream 1~32

Related Functional Groups of [ 325145-35-5 ]

Amides

Related Parent Nucleus of [ 325145-35-5 ]

Aliphatic Heterocycles

Piperazines

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[ 325145-35-5 ]

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[ 325145-35-5 ]